Facile Synthesis of Membrane-embedded Peptides Utilizing Lipid Bilayer-assisted Chemical Ligation. A. Otaka, S. Ueda, K. Tomita, Y. Yano, H. Tamamura, K. Matsuzaki, and N. Fujii.
Chem. Commun. 2004, 1722-1723.
Possible Involvement of the 1 Isoform of 5'AMP-Activated Protein Kinase in Oxidative-Stress-Stimulated Glucose Transport in Skeletal Muscle. T. Toyoda, T. Hayashi, L. Miyamoto, S. Yonemitsu, M. Nakano, S. Tanaka, K. Ebihara, H. Masuzaki, K. Hosoda, G. Inoue, A. Otaka, K. Sato, T. Fushiki, and K. Nakao. Am. J. Physiol. Endocrinol. Metab. 2004, 287, E166-173.
Identification of a CXCR4 antagonist, a T140 analog, as an anti-rheumatoid arthritis agent. H. Tamamura, M. Fujisawa, K. Hiramatsu, M. Mizumoto, H. Nakashima, N. Yamamoto, A. Otaka, and Fujii. FEBS Lett. 2004, 569, 99-104.
HIV protease inhibitor, nelfinavir, inhibits replication of SARS-associted coronavirus. N. Yamamoto, R.Yang, Y. Yoshinaka, S. Amari, T. Nakano, J. Cinatl, H. Rabenau, H.W. Doerr, G. Hunsmann, A. Otaka, H. Tamamura, N. Fujii, and N. Yamamoto. Biochem. Biophys. Res. Commun. 2004, 318, 719-725.
Synthesis of Fluorine-Containing Bioisosteres Corresponding to Phosphoamino Acids and Dipeptide Units. A. Otaka, E. Mitsuyama, J. Watanabe, H. Watanabe, and N. Fujii. Biopolymers 2004, 76, 140-149.
SmI2-mediated Reduction of g,g-Difluoro-a,b-enoates and Its Application to the Synthesis of (Z)-Fluoroalkene-type Dipeptide Isosteres. A. Otaka, J. Watanabe, A. Yukimasa, H. Watanabe, T. Kinoshita, S. Oishi, H.Tamamura, and N. Fujii. J. Org. Chem. 2004, 69, 1634-1645.
Topochemical exploration of potent compounds using retro-enantiomer libraries of cyclic pentapeptides. H. Tamamura, M. Mizumoto. K. Hiramatsu, S. Kusano, S. Terakuba, N. Yamamoto, J. O. Trent, Z. Wang, S.C. Peiper, H. Nakashima, A. Otaka, and N. Fujii. Org. Biomol. Chem. 2004, 2, 1-4.
Molecular Size Reduction of a Potent CXCR4-Chemokimne Antagonists Using Orthogona Combination of Conformation-based and Sequence-based Libraries. N. Fujii, S. Oishi, K. Hiramatsu, T. Araki, S. Ueda, H. Tamamura, A. Otaka, S. Kusano, S. Terakubo, H. Nakashima, J.A. Broach, J.H. Trent, Z.-x. Wang, and S. C. Peiper. Angew. Chem. Int Ed. Engl. 2003, 42, 3251-3253.
T140 Analogs as CXCR4 Antagonists Identified as Anti-metastatic Agents in the Treatment of Breast Cancer. H. Tamamura, A. Hori, N. Kanzaki, K. Hiramatsu, M. Mizumoto, H. Nakashima, N.Yamamoto, A. Otaka, and N. Fujii. FEBS Lett. 2003, 550, 79-83.
Application of Samarium Diiodide (SmI2)-induced Reduction of g-Acetoxy-a,b-enoates with a-Specific Kinetic Electrophilic Trapping for the Synthesis of Amino Acid Derivatives. A. Otaka, A.Yukimasa, J. Watanabe, Y. Sasaki, S. Oishi, H. Tamamura, and N. Fujii. Chem. Commun. 2003, 1834-1835
Enhancement of the T140-based pharmacophores leads to the development of more potent and bio-stable CXCR4 antagonists. H.Tamamura, K. Hiramatsu, M. Mizumoto, S. Ueda, S. Kusano, S. Terakubo, M. Akamatsu, N. Yamamoto, J.O. Trent, Z. Wang, S.C. Peiper, H. Nakashima, A. Otaka, and N. Fujii. Org. Biomol. Chem. 2003, 1, 3663-3669.
Synthesis of potent CXCR4 inhibitors possessing low cytotoxicity and improved biostability based on T140 derivatives. H. Tamamura, K. Hiramatsu, S. Kusano, S. Terakubo, N. Yamamoto, J. O. Trent, Z. Wang, S. C. Peiper, H. Nakashima, A. Otaka, and N. Fujii. Org. Biomol. Chem. 2003, 1, 3656-3662.
Synthesis of Potent g-Secretase Inhibitors Containing a Hydroxyethylamine Dipeptide Isostere and Their Structure-Activity Relationship Studies. H. Tamamura, T. Kato, A. Otaka, and N. Fujii, Org. Biomol. Chem. 2003, 1, 2468-2473.
Reduction of Peptide Character of HIV Protease Inhibitors that Exhibit NanomolarPotency against Multi-drug Resistant HIV-1 Strains. H. Tamamura, Y. Koh, S. Ueda, Y. Sasaki, T. Yamasaki, M. Aoki, K. Maeda, Y. Watai, H. Arikuni, A. Otaka, H. Mitsuya, and N. Fujii. J. Med. Chem. 2003, 46, 1764-1768.
Remodeling of gp41-C34 Peptide Leads to Highly Effective Inhibitors of the Fusion of HIV-1 with Target Cells. A. Otaka, M. Nakamura, D. Nameki, E. Kodama, S. Uchiyama, S. Nakamura, H. Nakano, H. Tamamura, Y. Kobayashi, M. Masuoka, and N. Fujii. Angew. Chem. Int. Ed. 2002, 41, 2937-2940.
Diastereoselective Synthesis of New y[(E)-CH=CMe]- and y[(Z)-CH=CMe]-type Alkene Dipeptide Isosteres by Organocopper Reagents and Application to Conformationally Restricted Cyclic RGD Peptidomimetics. S. Oishi, T. Kamano, A. Niida, Y. Odagaki, N. Hamanaka, M. Yamamoto, K. Ajito, H. Tamamura, A. Otaka, and N. Fujii. J. Org. Chem. 2002, 67, 6162-6173.
Regio- and Stereoselective Synthesis of (E)-Alkene trans-Xaa-Pro Dipeptide Mimetics Utilizing Organocopper-Mediated Anti-SN2' Reactions. A. Otaka, F. Katagiri, T. Kinoshita, Y. Odagaki, S. Oishi, H. Tamamura, N. Hamanaka, and N. Fujii. J. Org. Chem. 2002, 67, 6152-6161.
Identification of cell binding sites in the laminin alpha5-chain G domain. M. Makino, I. Okazaki, S. Kasai, N. Nishi, M. Bougaeva, B. S. Weeks, A. Otaka, P. K. Nielsen, Y. Yamada, and M. Nomizu. Exp. Cell Res. 2002, 277, 95-106.
Regio- and stereoselective ring-opening of chiral 1,3-oxazolidin-2-one derivatives by organocopper reagents provides novel access to di-, tri- and tetra-substituted alkene dipeptide isosteres. Shinya Oishi, Ayumu Niida, Takae Kamano, Yoshihisa Miwa, Tooru Taga, Yoshihiko Odagaki, Nobuyuki Hamanaka, Mikio Yamamoto, Keiichi Ajito, Hirokazu Tamamura, Akira Otaka, Nobutaka Fujii. J. Chem. Soc., Perkin Trans. 1, 2002, 1786-1793.
Certification of the Critical Importance of L-3-(2-Naphthyl)alanine at Position 3 of a Specific CXCR4 Inhibitor, T140, Leads to an Exploratory Performance of Its Downsizing Study. H. Tamamura, A. Omagari, K. Hiramatsu, S. Oishi, H. Habashita, T. Kanamoto, K. Gotoh, N. Yamamoto, H. Nakashima, A. Otaka & N. Fujii. Bioorg. Med. Chem. 2002, 10, 1417-1426.
Synthesis and evaluation of pseudopeptide analogues of a specific CXCR4 inhibitor, T140: The insertion of an (E)-alkene dipeptide isostere into the bII'-turn moiety. H. Tamamura, K. Hiramatsu, K. Miyamoto, A. Omagari, S. Oishi, H. Nakashima, N. Yamamoto, Y. Kuroda, T. Nakagawa, A. Otaka, & N. Fujii. Bioorg Med Chem Lett., 2002, 12, 923-928.
Trojan p16 peptide suppresses pancreatic cancer growth and prolongs survival in mice. R. Hosotani, Y. Miyamoto, K. Fujimoto, R. Doi, A. Otaka, N. Fujii and M. Imamura. Clin. Cancer Res. 2002, 8, 1271-1276.
Efficient stereoselective synthesis of peptidomimetics containing hydroxyethylamine dipeptide isosteres utilizing the aza-Payne rearrangement and O, N-acyl transfer reactions. Hirokazu Tamamura, Tadakazu Hori, Akira Otaka, Nobutaka Fujii. J. Chem. Soc., Perkin Trans. 1, 2002, 998-999.
Diastereoselective Synthesis of y[(E)-CMe=CH]- and y[(E)-CMe=CMe]- Type Dipeptide Isosteres Based on Organocopper-Mediated anti-S(N)2' Reaction. S. Oishi, A. Niida, T. Kamano, Y. Odagaki, H. Tamamura, A. Otaka, N. Hamanaka, and N. Fujii. Org. Lett. 2002, 4, 1055-1058.
Diastereoselective Synthesis of y[(E)-CH=CMe]- and y[(Z)-CH=CMe]-Type Dipeptide Isosteres by Organocopper-Mediated anti-S(N)2' Reaction. S. Oishi, T. Kamano, A. Niida, Y. Odagaki, H. Tamamura, A. Otaka, N. Hamanaka, and N. Fujii. Org. Lett. 2002, 4, 1051-1054.
Notch receptor cleavage depends on but is not directly executed by presenilins. Y. Taniguchi, H. Karlstrom, J. Lundkvist, T. Mizutani, A. Otaka, M. Vestling, A. Bernstein, D. Donoviel, U. Lendahl, & T. Honjo. Proc. Natl. Acad. Sci. U S A., 2002, 99, 4014-4019.
Heterodimer Formation between the Antimicrobial Peptides Magainin 2 and PGLa in Lipid Bilayers: A Cross-linking Study. T. Hara, Y. Mitani, K. Tanaka, N. Uematsu, A. Takakura, T. Tachi, H. Kodama, M. Kondo, H. Mori, A. Otaka, N. Fujii and K. Matsuzaki. Biochemistry, 2001, 40, 12395-12399.
Stereoselective Synthesis of a Set of Two Functionalized (E)-Alkene Dipeptide Isosteres of L-Amino Acid-L-Glu and L-Amino Acid-D-Glu. S. Oishi, H. Tamamura, M. Yamashita, N. Hamanaka, A. Otaka, and N. Fujii. J. Chem. Soc., Perkin Trans 1 2001, 2445-2451.
Synthesis and Evaluation of Bifunctional anti-HIV Agents Based on Specific CXCR4 Antagonists-AZT Conjugation. H. Tamamura, A. Omagari, K. Hiramatsu, T. Kanamoto, K. Gotoh, K. Kanbara, N. Yamamoto, H. Nakashima, A. Otaka, and N. Fujii. Bioorg. Med. Chem. 2001, 9, 2179-2187.
Development of Specific CXCR4 Inhibitors Possessing High Selectivity Indexes as Well as Complete Stability in Serum Based on an Anti-HIV Peptide T140. H. Tamamura, A. Omagari, K. Hiramatsu, K. Gotoh, T. Kanamoto, Y. Xu, E. Kodama, M. Matsuoka, H. Hattori, N. Yamamoto, H. Nakashima, A. Otaka, and N. Fujii. Bioorg. Med. Chem. Lett. 2001, 11, 1897-1902.
Phospho-azatyrosine, a Less Effective Protein-Tyrosine Phosphatase Substrate Than Phosphotyrosine. T. R. Burke, Jr., Z-J. Yao, B. Ye, K. Miyoshi, A. Otaka, L. Wu, and Z-Y. Zhang. Bioorg. Med. Chem. Lett. 2001, 11, 1265-1268.
New Access to a-Substituted (Z)-Fluoroalkene Dipeptide Isosteres Utilizing Organocopper Reagents under "Reduction-Oxidative Alkylation (R-OA)" Conditions. A. Otaka, H. Watanabe, A. Yukimasa, S. Oishi, H. Tamamura, and N. Fujii. Tetrahedron Lett. 2001, 42, 5443-5446.
Conformational Study of a Highly Specific CXCR4 Inhibitor, T140, Disclosing the Close Proximity of Its Intrinsic Pharmacophores Associated with Strong anti-HIV Activity. H. Tamamura, M. Sugioka, Y. Odagaki, A. Omagari, Y. Kan, S. Oishi, H. Nakashima, N. Yamamoto, S. C. Peiper, N. Hamanaka, A. Otaka, and N. Fujii. Bioorg. Medchem. Lett. 2001, 11, 359-362.
Synthesis of (Z)-Fluoroalkene Dipeptide Isosteres Utilizing Organocopper-mediated Reduction of g,g-Difluoro-a,b-enoates. A. Otaka, H. Watanabe, E. Mitsuyama, A. Yukimasa, H. Tamamura, and N. Fujii. Tetrahedron Lett. 2001, 42, 285-287.
Pharmacophore Identification of a Specific CXCR4 Inhibitor, T140, Leads to Development of Effective anti-HIV Agents with Very High Selectivity Indexes. H. Tamamura, A. Omagari, S. Oishi, T. Kanamoto, N. Yamamoto, S.C. Peiper, H. Nakashima, A. Otaka, and N. Fujii. Bioorg. Medchem. Lett. 2000, 10, 2633-2637.
Cell Adhesive Sequences in Mouse Laminin beta1 Chain. M. Nomizu, Y. Kuratomi, M. L. Ponce, S. Y. Song, K. Miyoshi, A. Otaka, S. K. Powell, M. P. Hoffman, H. K. Kleinman, and Y. Yamada. Arch Biochem Biophys. 2000, 378, 311-320.
Interactions between Local Anesthetics and Na+ Channel Inactivation Gate Peptides in Phosphatidylserine Suspensions as Studied by 1H-NMR Spectroscopy. Y. Kuroda, K. Miyamoto, K. Tanaka, Y. Maeda, J. Ishikawa, R. Hinata, A. Otaka, N. Fujii, and T. Nakagawa. Chem Pharm Bull. 2000, 48, 1293-1298.
Inhibition of pRb Phosphorylation and Cell Cycle Progression by an Antennapedia-p16(INK4A) Fusion Peptide in Pancreatic Cancer Cells. K. Fujimoto, R. Hosotani, Y. Miyamoto, R. Doi, T. Koshiba, A. Otaka, N. Fujii, R. D. Beauchamp, and M. Imamura. Cancer Lett. 2000, 159, 151-158.
Ca(2+)-Independent Activity of Ca(2+)/Calmodulin-dependent Protein Kinase II Involved in Stimulation of Neurite Outgrowth in Neuroblastoma Cells. Y. Sogawa, Y. Yoshimura, A. Otaka, and T. Yamauchi. Brain Res. 2000, 881, 165-175.
Structural Study of Sodium Channel Inactivation Gate Peptide Including an Isoleucine-phenylalanine-methionine Motif and Its Analogous Peptide (phenylalanine/glutamine) in Trifluoroethanol Solutions and SDS Micelles. Y. Kuroda, K. Miyamoto, M. Matsumoto, Y. Maeda, K. Kanamori, A. Otaka, N. Fujii, and T. Nakagawa. J. Peptide Res. 2000, 56, 172-184.
A New Practical Strategy for the Synthesis of Long-chain Phosphopeptide. K. Miyoshi, A. Otaka, M. Kaneko, H. Tamamura, and N. Fujii. Chem. Pharm. Bull. 2000, 48, 1230-1233.
Development of New Methodology for the Synthesis of Functionalized a-Fluorophosphonates and Its Practical Application to the Preparation of Phosphopeptide Mimetics. A. Otaka, E. Mitsuyama, H. Watanabe, H. Tamamura, and N. Fujii. Chem. Commun. 2000, 1081-1082.
Stereoselective Synthesis of CF2-Substituted Phosphothreonine Mimetics and Their Incorporation into Peptides Using Newly Developed Deprotection Procedures. A. Otaka, E. Mitsuyama, T. Kinoshita, H. Tamamura, and N. Fujii. J. Org. Chem. 2000, 65, 4888-4899.
Development of New Deprotecting Methodologies for Peptides and Application to Studies on Signaling Mechanism. A. Otaka. Yakugaku zasshi 2000, 120, 54-67.
1H-NMR and Circular Dichroism Spectroscopic Studies on Changes in Secondary Structures of the Sodium Channel Inactivation Gate Peptides as Caused by the Pentapeptide KIFMK. Y. Kuroda, Y. Maeda, K. Miyamoto, K. Tanaka, K. Kanaori, A. Otaka, N. Fujii, and T. Nakagawa. Biophys. J. 1999, 77, 1363-1373.
Induction of Human Leukocyte Antigen (HLA)-A2-restricted and MAGE-3-gene-derived Peptide-specific Cytolytic T Lymphocytes Using Cultured Dendritic Cells from an HLA-A2 Esophageal Cancer Patient. S. Kanaoka, S. Yamasaki, T. Okino, N. Inoue, Y. Shimada, M. Kaneko, A. Otaka, N. Fujii, and M. Imamura. J. Surg. Oncol. 1999, 71, 16-21.
Regiospecific Ring-opening Reactions of b-Aziridinyl a,b-enoates with Acids: Application to the Stereoselective Synthesis of a couple of Diastereoisomeric (E)-Alkene Dipeptide Isosteres from a Single b-Aziridinyl a,b-enoate and to the Convenient Preparation of Amino alcohols Bearing a,b-Unsaturated Ester Groups. H. Tamamura, M. Yamashita, Y. Nakajima, K. Sakano, A. Otaka, H. Ohono, T. Ibuka, and N. Fujii. J. Chem. Soc. Perkin Trans. 1 1999, 2983-2996.
Unambiguous Synthesis of Stromal Cell-derived Factor-1 by Regioselective Disulfide Bond Formation Using a DMSO-aqueous HCl System. H. Tamamura, F. Matsumoto, K. Sakano, A. Otaka, T. Ibuka, and N. Fujii. Chem. Commun. 1998, 151-152.
Convenient One-pot Synthesis of Cystine-containing Peptides Using the Trimethylsilyl Chloride-dimethyl sulfoxide/trifluoroacetic Acid System and Its Application to the Synthesis of Bifunctional anti-HIV Compounds 1. H. Tamamura, T. Ishihara, H. Oyake, M. Imai, A. Otaka, T. Ibuka, R. Arakaki, H. Nakashima, T. Murakami, M. Waki, A. Matsumoto, N. Yamamoto, and N. Fujii. J. Chem. Soc. Perkin Trans. 1 1998, 495-500.
Cell Binding Sequences in Mouse Laminin alpha1 Chain. M. Nomizu, Y. Kuratomi, K. M. Malinda, S. Y. Song, K. Miyoshi, A. Otaka, S. K. Powell, M. P. Hoffman, H. K. Kleinman, and Y. Yamada. J. Biol. Chem. 1998, 273, 32491-32499.
A Low-molecular-weight Inhibitor against the Chemokine Receptor CXCR4: a Strong anti-HIV Peptide T140. H. Tamamura, Y. Xu, T. Hattori, X. Zhang, R. Arakaki, K. Kanbara, A. Omagari, A. Otaka, T. Ibuka, N. Yamamoto, H. Nakashima, and N. Fujii. Biochem. Biophys. Res. Commun. 1998, 253, 877-882.
Pharmacophore Identification of a Chemokine Receptor (CXCR4) Antagonist, T22 ([Tyr(5,12),Lys7]-polyphemusin II), which Specifically Blocks T cell-line-tropic HIV-1 Infection. H. Tamamura, M. Imai, T. Ishihara, M. Masuda, H. Funakoshi, H. Oyake, T. Murakami, R. Arakaki, H. Nakashima, A. Otaka, T. Ibuka, M. Waki, A. Matsumoto, N. Yamamoto, and N. Fujii. Bioorg. Med. Chem. 1998, 6, 1033-1041.
Downsizing of an HIV-cell Fusion Inhibitor, T22 ([Tyr5,12, Lys7]-polyphemusin II), with the Maintenance of anti-HIV Activity and Solution Structure. H. Tamamura, M. Waki, M. Imai, A. Otaka, T. Ibuka, K. Waki, K. Miyamoto, A. Matsumoto, T. Murakami, H. Nakashima, N. Yamamoto, and N. Fujii. Bioorg. Med. Chem. 1998, 6, 473-479.
Effective Lowly Cytotoxic Analogs of an HIV-cell Fusion Inhibitor, T22 ([Tyr5,12, Lys7]-polyphemusin II). H. Tamamura, R. Arakaki, H. Funakoshi, M. Imai, A. Otaka, T. Ibuka, H. Nakashima, T. Murakami, M. Waki, A. Matsumoto, N. Yamamoto, and N. Fujii. Bioorg. Med. Chem. 1998, 6, 231-238.
14-3-3beta Protein Associates with Insulin Receptor Substrate 1 and Decreases Insulin-stimulated Phosphatidylinositol 3'-kinase Activity in 3T3L1 Adipocytes. A. Kosaki, K. Yamada, J. Suga, A. Otaka, H. Kuzuya. J. Biol. Chem. 1998, 273, 940-944.
Identification of Cell Binding Sequences in Mouse Laminin Gamma1 Chain by Systematic Peptide Screening. M. Nomizu, Y. Kuratomi, S. Y. Song, M. L. Ponce, M. P. Hoffman, S. K. Powell, K. Miyoshi, A. Otaka, H. K. Kleinman, and Y. Yamada. J. Biol. Chem. 1997, 272, 32198-32205.
Regiospecific Ring-opening Reactions of Aziridines Bearing an a,b-Unsaturated Ester Group with Trifluoroacetic Acid or Methanesulfonic Acid: Application to the Stereoselective Synthesis of (E)-Alkene Dipeptide Isosteres. H. Tamamura, M. Yamashita, H. Muramatsu, H. Ohno, T. Ibuka, A. Otaka, and N. Fujii. Chem. Commun. 1997, 2327-2328.
Regio- and Stereoselectivity in Reactions of 2,3-cis- and trans-3-Alkyl-2-Vinylaziridines with Organocopper Reagents: Importance of 2,3-cis-Stereochemistry in Controlling Selectivity. H. Aoyama, N. Mimura, H. Ohno, K. Ishii, A. Toda, H. Tamamura, A. Otaka, N. Fujii, and T. Ibuka. Tetrahedron Lett. 1997, 38, 7383-7386.
Palladium-Catalyzed Reductive Ring Opening with Formic Acid of Aziridines Bearing an a,b-Unsaturated Ester Group. H. Ohno, N. Mimura, A. Otaka, H. Tamamura, N. Fujii, T. Ibuka, I. Shimizu, A. Satake, and Y. Yamamoto. Tetrahedron 1997, 53, 12933-12946.
An anti-HIV peptide, T22, forms a highly active complex with Zn(II). H. Tamamura, A. Otaka, T. Murakami, T. Ibuka, K. Sakano, M. Waki, A. Matsumoto, N. Yamamoto, and N. Fujii. Biochem. Biophys. Res. Commun. 1996, 229, 648-652.
Interaction of an anti-HIV peptide, T22, with gp120 and CD4. H. Tamamura, A. Otaka, T. Murakami, T. Ishihara, T. Ibuka, M. Waki, A. Matsumoto, N. Yamamoto, and N. Fujii. Biochem. Biophys. Res. Commun. 1996, 219, 555-559.
Analysis of the interaction of an anti-HIV peptide, T22 ([Tyr5, 12, Lys7]-polyphemusin II), with gp120 and CD4 by surface plasmon resonance. H. Tamamura, T. Ishihara, A. Otaka, T. Murakami, T. Ibuka, M. Waki, A. Matsumoto, N. Yamamoto, and N. Fujii. Biochim. Biophys. Acta 1996, 1298, 37-44.
Mechanism of Laminin Chain Assembly into a Triple-Stranded Coiled-Coil Structure. M. Nomizu, A. Utani, K. Beck, A. Otaka, P. P. Roller and Y. Yamada. Biochemistry 1996, 35, 2885-2893.
Preparation of Na-Boc 4-O-Diethylphosphono-L-azatyrosine, a Reagent Potentially Useful for the Synthesis of Signal Transduction Related Peptides. B. Ye, A. Otaka and T.R. Burke, Jr. Synlett. 1996, 459-460.
Conformational Analysis of Cyclic Hexapeptides Designed as Constrained Ligands for the SH2 Domain of the p85 Subunit of Phosphatidylinositol-3-OH Kinase. J. J. Barchi, Jr., M. Nomizu, A. Otaka, P. P. Roller, and T. R. Burke, Jr. Biopolymers 1996, 38, 191-208.
Aza-Payne Rearrangement of Activated 2-Aziridinemethanols and 2,3-Epoxy Amines under Basic Conditions. T. Ibuka, K. Nakai, H. Habashita, Y. Hotta, A. Otaka, H. Tamamura, N. Fujii, N. Mimura, Y. Miwa, T. Taga, Y. Chounan and Y. Yamamoto. J. Org. Chem. 1995, 60, 2044-2058.
SN2' Ring opening of aziridines bearing an a,b-unsaturated ester group with organocopper reagents. A new stereoselective synthetic route to (E)-alkene dipeptide isosteres. N. Fujii, K. Nakai, H. Tamamura, A. Otaka, N. Mimura, Y. Miwa, T. Taga, Y. Yamamoto and T. Ibuka. J. Chem. Soc., Perkin Trans. 1 1995, 1359-1371.
A One-pot Aza-Payne Rearrangement-Epoxide Ring Opening Reaction of 2-Aziridinemethanols: A Regio- and Stereoselective Synthetic Route to Diastereomerically Pure 1,2-Amino Alocohols. K. Nakai, T. Ibuka, A. Otaka, H. Tamamura, N. Fujii and Y. Yamamoto. Tetrahedron Lett. 1995, 36, 6247-6250.
Identification of Cell Binding Sites in the Laminin a1 Chain Carboxyl-terminal Globular Domain by Systematic Screening of Synthetic Peptides. M. Nomizu, W. H. Kim, K. Yamamura, A. Utani, S.-Y. Song, A. Otaka, P. P. Roller, H. K. Kleinman and Y. Yamada. J. Biol. Chem. 1995, 270, 20583-20590.
Why Is Phosphonodifluoromethyl Phenylalanine a More Potent Inhibitory Moiety Than Phosphonomethyl Phenylalanine toward Protein-Tyrosine Phosphatases. L. Chen, L. Wu, A. Otaka, M. S. Smyth, P. P. Roller, T. R. Burke, Jr., J. Hertog and Z-Y. Zhang. Biochem. Biophys. Res. Commun. 1995, 216, 976-984.
Development of Efficient Two-step Deprotection Methodology for Dimethyl-protected Phosphoamino Acid-Containing Peptide Resins and Its Application to the Practical Synthesis of Phosphopeptides. A. Otaka, K. Miyoshi, M. Kaneko, H. Tamamura, N. Fujii, M. Nomizu, T. R. Burke, Jr., and P. P. Roller. J. Org. Chem. 1995, 60, 3967-3974.
Synthesis of Protegrin-related Peptides and their Antibacterial and Anti-Human Immunodeficiency Virus Activity. H. Tamamura, T. Murakami, S. Horiuchi, K. Sugihara, A. Otaka, W. Takada, T. Ibuka, M. Waki, N. Yamamoto, and N. Fujii. Chem. Pharm. Bull. 1995, 45, 853-858.
Disulfide Bond-forming Reaction using Dimethylsulfoxide/aqueous HCl System and Its Application to Regioselective Two Disulfide Bond Formation. H. Tamamura, A. Otaka, J. Nakamura, K. Okubo, T. Koide, K. Ikeda, T. Ibuka, and N. Fujii. Int. J. Peptide Protein Res. 1995, 45, 312-319.
Inhibition of TCR Signalling in Jurkat T Cells by a PTP-ase-resistant Phospho-TAM Peptide Analog. R. L. Wange, N. Isakov, T. R. Burke, Jr., A. Otaka, P. P. Roller, J. D. Watts, R. Aebersold, L. E. Samelson. J. Biol. Chem. 1995, 270, 944-948.
Practical Synthesis of Phosphopeptides Using Dimethyl-protected Phosphoamino Acid Derivatives. A. Otaka, K. Miyoshi, P. P. Roller, T. R. Burke, Jr., H. Tamamura, and N. Fujii. J. Chem. Soc., Chem. Commun. 1995, 387-389.
Solution-Phase Synthesis of an Anti-human Immunodeficiency Virus Peptide, T22 ([Tyr5,12, Lys7]-Polyphemusin II), and the Modification of Trp by the p-Methoxybenzyl Group of Cys during Trimethylsilyl Trifluoromethanesulfonate Deprotection. H. Tamamura, A. Otaka, W. Takada, Y. Terakawa, H. Yoshizawa, M. Masuda, T. Ibuka, T. Murakami, H. Nakashima, M. Waki, A. Matsumoto, N. Yamamoto, and N. Fujii. Chem. Pharm. Bull. 1995, 43, 12-18.
Synthesis and Application of N-Boc-L-2-amino-4-(diethylphosphono)-4,4-difluorobutanoic acid for Solid-Phase Synthesis of Nonhydrolyzable Phosphoserine Peptide Analogue. A. Otaka, K. Miyoshi, H. Kubota, T.R. Burke, Jr., P.P. Roller, H. Tamamura, and N. Fujii. Tetrahedron Lett. 1995, 36, 927-930.
Structure-Activity Relationships of An Anti-HIV Peptide, T-22. H. Tamamura, T. Murakami, M. Masuda, A. Otaka, W. Takada, T. Ibuka, H. Nakashima, M. Waki, A. Matsumoto, N. Yamamoto, and N. Fujii. Biochem. Biophys. Res. Commun. 1994, 205, 1729-1735.
(E)-Stereoselective Synthesis of Vinylglycines from (R)-Serine via Organocopper-BF3 and Related Reagents. T. Ibuka, K. Suzuki, H. Habashita, A. Otaka, H. Tamamura, N. Mimura, Y. Miwa, T. Taga, and N. Fujii. J. Chem. Soc., Chem. Commun. 1994, 2151-2152.
Synthesis of Optically Pure 2-Aziridinemethanols: Versatile Synthetic Building Blocks. N. Fujii, K. Nakai, H. Habashita, Y. Hotta, H. Tamamura, A. Otaka, and T. Ibuka. Chem. Pharm. Bull. 1994, 42, 2241-2250.
Assembly of Synthetic Laminin Peptides into a Triple-Stranded Coiled-Coil Structure. M. Nomizu, A. Otaka, A. Utani, P. P. Roller, and Y. Yamada. J. Biol. Chem. 1994, 269, 30386-30392.
Lymphocytes and Promonocytes Attach to The Synthetic [Tyr5,12, Lys7]-Polyphemusin II Peptide (T22). B. S. Weeks, M. Nomizu, A. Otaka, C. A. Weston, A. Okusu, H. Tamamura, A. Matsumoto, N. Yamamoto, and N. Fujii. Biochem. Biophys. Res. Commun. 1994, 202, 470-475.
Molecular Parameters for the Anti-Human Immunodeficiency Virus Activity of T22 ([Tyr5,12, Lys7]-Polyphemusin II. A. Otaka, H. Tamamura, Y. Terakawa, M. Masuda, T. Koide, T. Murakami, H. Nakashima, K. Matsuzaki, K. Miyajima, T. Ibuka, M. Waki, A. Matsumoto, N. Yamamoto, and N. Fujii. Biol. Pharm. Bull. 1994, 17, 1669-1672.
Norleucine as a Replacement for Methionine in Phophatase-resistant Linear and Cyclic Peptides which Bind to p85 SH2 domains. P. P. Roller, A. Otaka, M. Nomizu, M. S. Smyth, J. J. Barchi, Jr., and T. R. Burke, Jr. Bioorg. Med. Chem. Lett. 1994, 4, 1879-1882.
Cyclic Peptide Inhibitors of Phosphoatidylinositol 3-kinase p85 SH2 Domain Binding. T. R. Burke, Jr., M. Nomizu, A. Otaka, M. S. Smyth, P. P. Roller, R. D. Case, G. Wolf, and S. E. Shoelson. Biochem. Biophys. Res. Commun. 1994, 201, 1148-1153.
Nonhydrolyzable Phosphotyrosyl Mimetics for The Preparation of Phosphatase Resistant SH2 Binding Peptides. T. R. Burke, Jr., M. S. Smyth, A. Otaka, M. Nomizu, P. P. Roller, G. Wolf, R. D. Case, and S. E. Shoelson. Biochemistry, 1994, 33, 6490-6494.
Synthesis of Phosphonomethyl-phenylalanine and Phosphotyrosine Containing Cyclic Peptides as Inhibitors of Protein Tyrosine Kinase / SH2 Interactions. M. Nomizu, A. Otaka, T. R. Burke, Jr., and P. P. Roller. Tetrahedron 1994, 50, 2691-2702.
Role of Disulfide Linkage in Tachyplesin-Lipid Interactions. K. Matsuzaki, M. Nakayama, M. Fukui, A. Otaka, S. Funakoshi, N. Fujii, K. Bessho, and K. Miyajima. Biochemistry 1993, 32, 11704-11710.
Multiplicity of Virus-encoded Helper T cell Epitopes Expressed on FBL-3 Tumor Cells. M. Iwashiro, T. Kondo, T. Shimizu, H. Yamagishi, K. Takahashi, Y. Matubayashi, T. Mauda, A. Otaka, N. Fujii, A. Ishimoto, M. Miyazawa, M. N. Robertson, B. Chesebro, and K. Kuribayashi. J. Virol. 1993, 67, 4533-4542.
Preparation of Peptide-carrying Microspheres with Bioactivity on Platelets. Y. Kasuya, K. Fujimoto, M. Miyamoto, T. Juji, A. Otaka, S. Funakoshi, N. Fujii, and H. Kawaguchi. J. Biomater. Sci. Polymer Edn. 1993, 4, 369-380.
Deprotection and Cleavage Methods for Protected Peptide Resins Containing 4-[(Diethylphosphono)difluoromethyl]-D,L-phenylalanine Residues. A. Otaka, T. R. Burke, Jr., M. S. Smyth, M. Nomizu, and P. P. Roller. Tetrahedron Lett. 1993, 34, 4931-4934.
Disulfide Bond Formation in S-Acetamidomethyl Cysteine-Containing Peptides by the Combination of Silver Trifluoromethanesulfonate and Dimethylsulfoxide / Aqueous HCl. H. Tamamura, A. Otaka, J. Nakamura, K. Okubo, T. Koide, K. Ikeda, and N. Fujii. Tetrahedron Lett. 1993, 34, 4931-4934.
Synthesis of 4-Phosphono(difluoromethyl)-D,L-phenylalanine and N-Boc and N-Fmoc Derivatives Suitably Protected for Solid-Phase Synthesis of Nonhydrolyzable Phosphotyrosyl Peptide Analogues. T. R. Burke, Jr., M. S. Smyth, A. Otaka, and P. P. Roller. Tetrahedron Lett. 1993, 34, 4125-4128.
Preparation of Fluoro- and Hydroxy-4-(phosphonomethyl)-D,L-phenylalanine Suitably Protected for Solid-Phase Synthesis of Peptides Containing Hydrolytically Stable Analogues of O-Phosphotyrosine. T. R. Burke, Jr., M. S. Smyth, M. Nomizu, A. Otaka, and P. P. Roller. J. Org. Chem. 1993, 58, 1336-1340.
Syntheses and Biological Activities of Selenium Analogs of a-Rat Atrial Natriuretic Peptide. T. Koide, H. Itoh, A. Otaka, M. Furuya, Y. Kitajima, and N. Fujii. Chem. Pharm. Bull. 1993, 41, 1596-1600.
A Comparative Study of the Solution Structures of Tachyplesin I and a Novel Anti-HIV Synthetic Peptides, T22([Tyr5,12, Lys7]-Polyphemusin II), Determined by Nuclear Magnetic Resonance. H. Tamamura, M. Kuroda, M. Masuda, A. Otaka, S. Funakoshi, H. Nakashima, N. Yamamoto, M. Waki, A. Matsumoto, J.M. Lancelin, D. Kohda, S. Tate, F. Inagaki, and N. Fujii. Biochim. Biophys. Acta 1993, 1163, 209-216.
Investigation of the Dimethylsulfoxide-Trifluoroacetic acid Oxidation System for the Synthesis of Cystine-Containing Peptides. T. Koide, A. Otaka, and N. Fujii. Chem. Pharm. Bull. 1993, 41, 1030-1034.
Direct Disulfide Formation from 2-Quinolinylmethyl Thioethers with Iron(III) or Copper(II) Salt. H. Yoshizawa, A. Otaka, H. Habashita, and N. Fujii. Chem. Lett. 1993, 803-806.
Synthetic Study on Selenocystine-Containing Peptides. T. Koide, H. Itoh, A. Otaka, H. Yasui, M. Kuroda, N. Esaki, K. Soda, and N. Fujii. Chem. Pharm. Bull. 1993, 41, 502-506.
Enzyme Immunoassay of Thyrotropin Releasing Hormone (TRH). M. Takeyama, A. Otaka, and N. Fujii. Chem. Pharm. Bull. 1992, 40, 2199-2201.
A Novel Anti-HIV Synthetic Peptide, T-22 ([Tyr5,12, Lys7]- Polyphemusin II). M. Masuda, H. Nakashima, T. Ueda, H. Naba, R. Ikoma, A. Otaka, Y. Terakawa, H. Tamamura, T. Ibuka, T. Murakami, Y. Koyanagi, M. Waki, A. Matsumoto, N. Yamamoto, S. Funakoshi, and N. Fujii. Biochem. Biophys. Res. Commun. 1992, 189, 845-850.
A Simple Synthesis of y[(E)CH=CH]Gly Dipeptide Isosters via Reductive Elimination of g-Oxygenated a, b-Enoates with Alkenylcopper Reagents. N. Fujii, H. Habashita, N. Shigemori, A. Otaka, T. Ibuka, M. Tanaka, and Y. Yamamoto. Tetrahedron Lett. 1991, 32, 4969-4972.
A Highly Stereoselective Synthesis of (E)-Alkene Dipeptide Isosters via Organocyanocopper-Lewis Acid Mediated Reaction. T. Ibuka, H. Habashita, A. Otaka, N. Fujii, Y. Oguti, T. Uyehara, and Y. Yamamoto. J. Org. Chem. 1991, 56, 4370-4382.
Selective Conversion of S-Protected Cysteine Derivatives to Cystine by Various Sulphoxide-Silyl Compound / Trifluoroacetic Acid Systems. T. Koide, A. Otaka, H. Suzuki, and N. Fujii. SynLett. 1991, 345-346.
Application of Dimethylsulphoxide(DMSO) / Trifluoroacetic Acid(TFA) Oxidation to The Synthesis of Cystine-Containing Peptide. A. Otaka, T. Koide, A. Shide, and N. Fujii. Tetrahedron Lett. 1991, 32, 1223-1226.
Solid Phase Peptide Synthesis of Human Endothelin Precursor Peptides Using Two-step Hard-acid Deprotection / Cleavage Methods. M. Nomizu, Y. Inagaki, A. Iwamatsu, T. Kashiwabara, H. Ohta, A. Morita, K. Nishikori, A. Otaka, N. Fujii, and P. P. Roller. Int. J. Peptide Protein Res. 1991, 38, 580-587.
Two-Step Hard Acid Deprotection / Cleavage Procedure for Solid Phase Peptide Synthesis. M. Nomizu, Y. Inagaki, T. Yamashita, A. Ohkubo, A. Otaka, N. Fujii, P.P. Roller, and H. Yajima. Int. J. Peptide Protein Res. 1991, 37, 145-152.
Microenzyme Immunoassay for The Measurement of Brain Natriuretic Peptide (BNP)-like Immunoreactivity in Porcine Plasma. M. Takeyama, F. Yasunaga, A. Otaka, N. Fujii, and H. Yajima. J. Immunological Methods 1990, 130, 217-222.
Immuno-affinity Purification of Specific Antibodies against Human Gastrin Releasing Peptide (h-GRP) by the hGRP(1-8)-linked Polydimethylacrylamide Resin. M. Takeyama, T. Kino, L.L. Guo, A. Otaka, N. Fujii, and H. Yajima. Int. J. Peptide Protein Res. 1989, 33, 457-462.
Immuno-affinity Purification of Specific Antibodies against Vasoactive Intestinal Polypeptide (VIP) by the VIP(1-10)-linked Polydimethylacrylamide Resin. M. Takeyama, M. Hatano, A. Otaka, N. Fujii, and H. Yajima. Chem. Pharm. Bull. 1989, 37, 834-837.
S-Benzyloxymethylcysteine, Its Properties and Application in the Synthesis of Porcine Brain Natriuretic Peptide (pBNP). A. Otaka, H. Morimoto, N. Fujii, T. Koide, S. Funakoshi, and H. Yajima. Chem. Pharm. Bull. 1989, 37, 526-528.
Silver Trifluoromethanesulfonate, as an S-Deprotecting Reagent for the Synthesis of Cystine-Peptides. N. Fujii, A. Otaka, T. Watanabe, A. Okamachi, H. Tamamura, H. Yajima, Y. Inagaki, M. Nomizu, and K. Asano. J. Chem. Soc. Chem. Commun. 1989, 283-284.
New Strategy for the Chemical Synthesis of Proteins. H. Yajima, N. Fujii, S. Funakoshi, E. Murayama, T. Watanabe, and A. Otaka. Tetrahedron 1988, 44, 805-819.
Selective Transport of the Salts of Amino Acid Esters through an Organic Liquid Membrance with Antamanide as a Carrier. H. Kataoka, T. Katagi, H. Yajima, and A. Otaka. Chem. Pharm. Bull. 1988, 36, 3196-3198.
Human Parathyroid Hormone-Related Peptide Binds to the Parathyroid Hormone Receptors in Rat Osteosarcoma Cells. C. Shigeno, I. Yamamoto, N. Kitamura, K. Lee, T. Sone, K. Shiomi, T. Noda, A. Otaka, N. Fujii, H. Yajima, and J. Konishi. J. Biol. Chem. 1988, 263, 18369-18377.
Model Experiments for the Synthesis of Open-Chain Unsymmetrical Cystine-Peptides. N. Fujii, A. Otaka, S. Funakoshi, T. Watanabe, H. Arai, K. Bessho, and H. Yajima. J. Proteine Chemistry 1988, 7, 151-156.
Sulphoxide-directed Disulfide Bond forming Reaction for the Synthesis of Cystine Peptides. N. Fujii, A. Otaka, T. Watanabe, H. Arai, S. Funakoshi, K. Bessho, and H. Yajima. J. Chem. Soc. Chem. Commun. 1987, 1676-1678.
Synthesis of Second Human Calcitonin Gene-Related Peptide (b-hCGRP) by Application of a New Disulfide-bonding Reaction with Thallium(III) Trifluoroacetate. N. Fujii, T. Watanabe, A. Otaka, K. Bessho, I. Yamamoto, J. Konishi, and H. Yajima. Chem. Pharm. Bull. 1987, 35, 4769-4776.
Evaluation of Trimethylsilyl Bromide as a Hard Acid Deprotecting Reagent in Peptide Synthesis. N. Fujii, A. Otaka, N. Sugiyama, M. Hatano, and H. Yajima. Chem. Pharm. Bull. 1987, 35, 3880-3883.
Hard Acid Deprotecting Procedure for Peptide Synthesis. N. Fujii, A. Otaka, O. Ikemura, M. Hatano, A. Okamachi, S. Funakoshi, M. Sakurai, T. Shioiri, and H. Yajima. Chem. Pharm. Bull. 1987, 35, 3447-3452.
Trimethylsilyl Trifluoromethanesulfonate as a Useful Deprotecting Reagent in Both Solution and Solid Phase Peptide Synthesis. N. Fujii, A. Otaka, O. Ikemura, K. Akaji, S. Funakoshi, Y. Hayashi, Y. Kuroda, and H. Yajima. J. Chem. Soc. Chem. Commun. 1987, 274-275.
Synthesis of Cystine-Peptides by Oxidation of S-Protected Cysteine-Peptides with Thallium(III) Trifluooroacetate. N. Fujii, A. Otaka, S. Funakoshi, K. Bessho, T. Watanabe, K. Akaji, and H. Yajima. Chem. Pharm. Bull. 1987, 35, 2339-2347.
New Procedure for the Synthesis of Cystine-Peptides by Oxidation of S-Substituted Cysteine-Peptides with Thallium(III) Trifluoroacetate. N. Fujii, A. Otaka, S. Funakoshi, K. Bessho, and H. Yajima. J. Chem. Soc. Chem. Commun. 1987, 163-164.
Calcitonin Gene-Related Peptide Promotes Mechanical Nociception by Potentiating Release of Substance P from the Spinal Dorsal Horn in Rats. R. Oku, M. Satoh, N. Fujii, A. Otaka, H. Yajima, and H. Takagi. Brain Research 1987, 403, 350-354.
Possible Mechanisms of Positive Inotropic Action of Synthetic Human Calcitonin Gene-Related Peptide in Isolated Rat Atrium. M. Satoh, R. Oku, A. Maeda, N. Fujii, A. Otaka, S. Funakoshi, H. Yajima, and H. Takagi. Peptides 1986, 7, 631-635.
Human Calcitonin Gene-Related Peptide Possesses Weak Inhibitory Potency of Bone Resorption in vitro. I. Yamamoto, N. Kitamura, J. Aoki, C. Shigematu, M. Hino, K. Asonuma, K. Torizuka, N. Fujii, A. Otaka, and H. Yajima. Calcif. Tissue Int. 1986, 38, 339-341.
Binding Sites of Calcitonin Gene-Related Peptide(CGRP): Abudant Occurrences in Visceral Organs. H. Nakamuta, Y. Fukuda, M. Koida, N. Fujii, A. Otaka, S. Funakoshi, and H. Yajima. Japan J. Pharmacol. 1986, 42, 175-180.
Evaluation of b-Mentylaspartate for Peptide Synthesis. H. Yajima, S. Futaki, A. Otaka, T. Yamashita, S. Funakoshi, K. Bessho, N. Fujii, and K. Akaji. Chem. Pharm. Bull. 1986, 34, 4356-4361.
Synthesis of Des-1-Ala-des-a-amino-Human Calcitonin Gene-Related Peptide. A. Otaka, N. Fujii, S. Funakoshi, I. Yamamoto, K. Torizuka, T. Noda, K. Morita, and H. Yajima. Chem. Pharm. Bull. 1986, 34, 3915-3918.
Evaluation of S-1-Adamantylcysteine for Peptide Synthesis. N. Fujii, A. Otaka, S. Funakoshi, H. Yajima, O. Nishimura, and M. Fujino. Chem. Pharm. Bull. 1986, 34, 869-872.
Evaluation of Two b-Carboxyl Protecting Group of Aspartic Acid, Cycloheptyl and Cyclooctyl, for Peptide Synthesis. N. Fujii, M. Nomizu, S. Futaki, A. Otaka, S. Funakoshi, K. Akaji, K. Watanabe, and H. Yajima. Chem. Pharm. Bull. 1986, 34, 864-868.
Solution-Phase Synthesis of a 37-Residue Peptide Amide Corresponding to the Entire Amino Acid Sequence of Human Calcitonin Gene-Related Peptide(hCGRP). N. Fujii, A. Otaka, S. Funakoshi, M. Nomizu, K. Akaji, H. Yajima, I. Yamamoto, K. Torizuka, K. Kitagawa, T. Akita, K. Ando, T. Kawamoto, Y. Shimonishi, and T. Takao. Chem. Pharm. Bull. 1986, 34, 613-620.
reparation of Seven Peptide Fragments for the Synthesis of Human Calcitonin Gene-Related Peptide(hCGRP). N. Fujii, A. Otaka, S. Funakoshi, M. Nomizu, K. Akaji, H. Yajima, K. Kitagawa, T. Akita, K. Ando, and T. Kawamoto. Chem. Pharm. Bull. 1986, 34, 603-612.
Conventional Procedure for the Reduction of Methionine Sulfoxide. N. Fujii, S. Kuno, A. Otaka, S. Funakoshi, K. Takagi, and H. Yajima. Chem. Pharm. Bull. 1985, 33, 4587-4588.
Application of S-1-Adamantylcysteine to the Synthesis of a 37-Residue Peptide Amide Corresponding to Human Calcitonin Gene-Related Peptide(hCGRP). N. Fujii, H. Yajima, A. Otaka, S. Funakoshi, M. Nomizu, K. Akaji, K. Torizuka, K. Kitagawa, T. Akita, K. Ando, T. Kawamoto, Y. Shimonishi, and T. Takao. J. Chem. Soc. Chem. Comm