2024
K. Hidaka, D. Kobayashi, J. Hayashi, M. Denda, and A. Otaka
Advanced Insulin Synthesis by One-pot/stepwise Disulfide Bond Formation Enabled by Acid-activated S-Protected Cysteine Sulfoxide in the Presence of Chloride Anion
ChemRxiv, Organic Chemistry, 2024. (doi: 10.26434/chemrxiv-2024-jg5z3)
R. Miyajima, K. Tanegashima, N. Naruse, M. Denda, T. Hara*, and A. Otaka*
Identification of Low-Density Lipoprotein Receptor-Related Protein 1 as a CXCL14 Receptor Using Chemically Synthesized Tetrafunctional Probes
ACS Chem. Biol. 2024. (doi: 10.1021/acschembio.3c00717)
D. Kobayashi, M. Denda, J. Hayashi, K. Hidaka, Y. Kohmura, T. Tsunematsu, K. Nishino, H. Yoshikawa, K. Ohkawachi, K. Nigorikawa, T. Yoshimaru, N. Ishimaru, W. Nomura, T. Katagiri, H. Hosako, and A. Otaka
Sulfoxide-mediated Cys-Trp-selective bioconjugation that enables protein labeling and peptide heterodimerization
ChemRxiv, Organic Chemistry, 2024. (doi: 10.26434/chemrxiv-2024-tkv7w-v2)
2023
M. Imanishi, T. Inoue, K. Fukushima, R. Yamashita, R. Nakayama, M. Nojima, K. Kondo, Y. Gomi, H. Tsunematsu, K. Goto, L. Miyamoto, M. Funamoto, M. Denda, K. Ishizawa, A. Otaka, H. Fujino, Y. Ikeda, and K. Tsuchiya
CA9 and PRELID2; hypoxia-responsive potential therapeutic targets for pancreatic ductal adenocarcinoma as per bioinformatics analyses
J. Pharmacol. Sci. 2023, 153(4), 232-242. (doi: 10.1016/j.jphs.2023.10.003)
T. Tsuji, H. Tsunematsu, M. Imanishi, M. Denda, K. Tsuchiya, and A. Otaka
Enhanced tumor specific drug release by hypoxia sensitive dual-prodrugs based on 2-nitroimidazole
Bioorg. Med. Chem. Lett. 2023, 95. (doi: 10.1016/j.bmcl.2023.129484)
M. Neishi, H. Hamano, T. Niimura, M. Denda, K. Yagi, K. Miyata, T. J. Lin, T. Higashionna, M. Goda, Y. Zamami, K. Ishizawaand, and H. Nawa
Structural characterization of the optical isomers esomeprazole and omeprazole using the JADER and FAERS databases
Toxicol. Appl. Pharmacol. 2023, 475. (doi: 10.1016/j.taap.2023.116632)
K. Ohkawachi, K. Anzaki, D. Kobayashi, R. Kyan, T. Yasuda, M.Denda, N. Harada, A. Shigenaga, N. Inagaki, and A. Otaka*
Residue-Selective C-H Sulfenylation Enabled by Acid-Activated S-Acetamidomethyl Cysteine Sulfoxide with Application to One-Pot Stapling and Lipidation Sequence
Chem. Eur. J. 2023, 29(26). (doi:10.1002/chem.202300799)
2022
A. Otaka
Development of Naturally Inspired Peptide and Protein Chemistry
Chem. Pharm. Bull. 2022, 70(11), 748-764. (doi: 10.1248/cpb.c22-00623)
D. Kobayashi, E. Kuraoka, J. Hayashi, T. Yasuda, Y. Kohmura, M. Denda, N. Harada, N. Inagaki, and A. Otaka*
S-Protected cysteine sulfoxide-enabled tryptophan-selective modification with application to peptide lipidation
ACS Med. Chem. Lett. 2022, 13(7), 1125-1130. (doi:10.1021/acsmedchemlett.2c00161)
M. Denda, A. Otaka
Advances in Preparation of Peptide and Protein Thioesters Aiming to Use in Medicinal Sciences
Chem. Pharm. Bull. 2022, 70(5), 316-323. (doi: 10.1248/cpb.c21-01019)
D. Sato, M. Denda, H. Tsunematsu, N. Tanaka, I. Konishi, C. Komiya, A. Shigenaga, and A. Otaka*
Late-stage macrolactonisation enabled by tandem acyl transfers followed by desulphurisation
Chem. Commun. 2022, 58(17), 2918-2921. (doi: 10.1039/D1CC07248J)
M. Miyake*, M. Sobajima, K, Kurahashi, A. Shigenaga, M. Denda, A. Otaka, T. Saio, N. Sakane, H. Kosako, and S. Oyadomari*
Identification of an endoplasmic reticulum proteostasis modulator that enhances insulin production in pancreatic β cells
Cell Chemical Biology 2022, 29(6), 996-1009. (doi:10.1016/j.chembiol.2022.01.002)
2021
K. Nakae, S. Masui, A. Yonezawa, M. Hashimoto, R. Watanabe, K. Murata, K. Murakami, M. Tanaka, H. Ito, K. Yokoyama, N. Iwamoto, T. Shimada, M. Nakamura, M. Denda, K. Itohara, S. Nakagawa, Y. Ikemi, S. Imai, T. Nakagawa, M. Hayakari, and K. Matsubara
Potential Application of Measuring Serum Infliximab Levels in Rheumatoid Arthritis Management: A Retrospective Study based on KURAMA Cohort Data
PLOS ONE (doi:10.1371/journal.pone.0258601)
D. Kobayashi, Y. Kohmura, J. Hayashi, M. Denda, K. Tsuchiya, and A. Otaka*
Copper (II)-mediated C-H sulphenylation or selenylation of tryptophan enabling macrocyclization of peptides
Chem. Commun. 2021, 57, 10763-10766. (doi: 10.1039/D1CC04856B)
D. Kobayashi, Y. Kohmura, T. Sugiki, E. Kuraoka, M. Denda, T. Fujiwara, and A. Otaka*
Peptide Cyclization Mediated by Metal-Free S-Arylation: S-Protected Cysteine Sulfoxide as an Umpolung of Cysteine Nucleophile
Chem. Eur. J. 2021, 27(56), 14092-14099. (doi:10.1002/chem.202102420)
R. Iwase, N. Naruse, M. Nakagawa, R. Saito, A. Shigenaga, A. Otaka, T. Hara, and K. Tanegashima
Identification of Functional Domains of CXCL14 Involved in High-Affinity Binding and Intracellular Transport of CpG DNA
J. Immunol. 2021, 207(2), 459-469. (doi:10.4049/jimmunol.2100030)
J. V. V. Arafiles, H. Hirose, Y. Hirai, M. Kuriyama, M. M. Sakyiamah, W. Nomura, K. Sonomura, M. Imanishi, A. Otaka, H. Tamamura, and S. Futaki*
Discovery of a Macropinocytosis-Inducing Peptide Potentiated by Medium-Mediated Intramolecular Disulfide Formation
Angew. Chem. Int. Ed. 2021,60(21), 11928-11936. (doi: 10.1002/anie.202016754)
2020
M. Ueda, C. Komiya, S. Arii, K. Kusumoto, M. Denda, K. Okuhira, A. Shigenaga*, and A. Otaka*
Sequence-independent traceless method for preparation of peptide/protein thioesters using CPaseY-mediated hydrazinolysis
Chem. Pharm. Bull. 2020, 68, 1226-1232. (doi: 10.1248/cpb.c20-00674)
D. Kobayashi, N. Naruse, M. Denda, A. Shigenaga, and A. Otaka*
Deprotection of S-Acetamidomethyl Cysteine with Copper (II) and 1,2-Aminothiols under Aerobic Conditions
Org. Biomol. Chem. 2020, 18, 8638-8645. (doi: 10.1039/D0OB01475C)
K. Ohkawachi, D. Kobayashi, K. Morimoto, A. Shigenaga, M. Denda, K. Yamatsugu, M. Kanai, and A. Otaka*
Sulfanylmethyldimethylaminopyridine as a Useful Thiol Additive for Ligation Chemistry in Peptide/Protein Synthesis
Org. Lett. 2020, 22 (14), 5289-5293. (doi: 10.1021/acs.orglett.0c01383)
Atsushi Nakayama, A. Ohtani, T. Inokuma, D. Tsuji, H. Mukaiyama, Akira Nakayama, K. Itou, A. Otaka, K. Tanino, and K. Namba
Development of a 1,3a,6a-triazapentalene derivatives as a compact and thiol-specific fluorescent labeling reagent
Chem. Commun, 2020, Vol.3, 6. (doi: 10.1038/s42004-019-0250-0)
2019
T. Morisaki, A. Shigenaga*, and A. Otaka*
Development of a turn-on fluorescent traceable linker employing N-sulfanylethylcoumarinyl amide for enrichment and visualization of target proteins
Chem. Pharm. Bull. 2019, 68, 216-219. Current Topic “Drug Discovery: Recent Progress and the Future”(doi: 10.1248/cpb.c19-00726)
N. Naruse, D. Kobayashi, K. Ohkawachi, A. Shigenaga, and A. Otaka*
Copper-mediated deprotection of thiazolidine and selenazolidine derivatives applied to native chemical ligation
J. Org. Chem. 2020, 85, 1425-1433. JOC Special Issue “Modern Peptide and Protein Chemistry” (doi: 10.1021/acs.joc.9b02388)
T. Inokuma*, T. Sakakibara, T. Someno, K. Masui, A. Shigenaga, A. Otaka, and K. Yamada*
Asymmetric synthesis of α-amino phosphonic acids using stable imino phosphonate as a universal precursor
Chem. Eur. J. 2019, 25, 13829-13832. Hot Topic: Organocatalysis (doi: 10.1002/chem.201903572)
C. Komiya, A. Shigenaga*, J. Tsukimoto, M. Ueda, T. Morisaki, T. Inokuma, K. Itoh, and A. Otaka*
Traceless synthesis of protein thioesters using enzyme-mediated hydrazinolysis and subsequent self-editing of cysteinyl prolyl sequence
Chem. Commun. 2019, 55, 7029-7032. (doi: 10.1039/C9CC03583D)
H. Kawahara, N. Miyashita, K. Tachibana, Y. Tsuda, K. Morimoto, K. Tsuji, A. Shigenaga, A. Otaka, T. Ishida, and K. Okuhira*
A photo-activatable peptide mimicking functions of apolipoprotein A-I
Biol. Pharm. Bull. 2019, 42, 1019-1024. (doi: 10.1248/bpb.b19-00114)
2018
A. Otaka
Current Topics - Drug Discovery: Recent Progress and the Future Foreward
Chem. Pharm. Bull. 2018, 66, 189-190. (doi: 10.1248/cpb.c18-ctf6603)
T. Jichu #, T. Inokuma #, K. Aihara, T. Kohiki, K. Nishida, A. Shigenaga, K. Yamada, and A. Otaka* (#equal contribution)
A recyclable hydrophobic anchor-tagged asymmetric amino thiourea catalyst
ChemCatChem 2018, 10, 3402-3405. (doi: 10.1002/cctc.201800714)
T. Inokuma, K. Nishida, A. Shigenaga, K. Yamada, and A. Otaka*
Direct enantioselective indolylation of peptidyl imine for the synthesis of indolyl glycine-containing peptides
Heterocycles (Professor Tomioka's Special Issue) 2018, 97, (2), 1269-1287. (doi: 10.3987/COM-18-S(T)86)
H. Inaba*, A. Uemura, K. Morishita, T. Kohiki, A. Shigenaga, A. Otaka, and K. Matsuura*
Light-induced propulsion of a giant liposome driven by peptide nanofibre growth
Sci. Rep. 2018, 8, article number 6243. (doi: 10.1038/s41598-018-24675-7)
鳥取大学および日本の研究.comよりプレスリリース
N. Naruse, K. Ohkawachi, T. Inokuma, A. Shigenaga, and A. Otaka*
Resin-bound crypto-thioester for native chemical ligation
Org. Lett. 2018, 20, 2449-2453. (doi: 10.1021/acs.orglett.8b00795)
C. Mizuguchi, M. Nakamura, N. Kurimitsu, T. Ohgita, K. Nishitsuji, T. Baba, A. Shigenaga, T. Shimanouchi, K. Okuhira, A. Otaka, and H. Saito*
Effect of phosphatidylserine and cholesterol on membrane-mediated fibril formation by the N-terminal amyloidogenic fragment of apolipoprotein A-I
Sci. Rep. 2018, 8, article number 5497. (doi: 10.1038/s41598-018-23920-3)
A. Shigenaga*, N. Naruse, and A. Otaka
ProteoFind: A script for finding proteins that are suitable for chemical synthesis
Tetrahedron 2018, 74, 2291-2297. (doi: 10.1016/j.tet.2018.03.030) [徳島大学機関リポジトリ]
2017
T. Kohiki, Y. Nishikawa, T. Inokuma, A. Shigenaga*, and A. Otaka*
Chemical synthetic platform for chlorpromazine oligomers that were reported as photo-degradation products of chlorpromazine
Chem. Pharm. Bull. 2017, 65, 1161-1166. (doi: 10.1248/cpb.c17-00692) [徳島大学機関リポジトリ]
K. Tanegashima*, R. Takahashi, H. Nuriya, N. Naruse, K. Tsuji, A. Shigenaga, A. Otaka, and T. Hara*
CXCL14 acts as a specific carrier of CpG into dendritic cells and activates Toll-like receptor 9-mediated adaptive immunity
EBioMedicine 2017, 24, 247-256. (doi: 10.1016/j.ebiom.2017.09.012)
K. Aihara, T. Inokuma, T. Jichu, Z. Lin, F. Fu, K. Yamaoka, A. Shigenaga, D. Hutchins, E. Schmidt, and A. Otaka*
Cysteine-free intramolecular ligaiton of N-sulfanylethylanilide peptide using 4-mercaptobenzylphosphonic acid: Synthesis of cyclic peptide, trichamide
Synlett 2017, 28, 1944-1949. Cluster: Recent Advances in Protein and Peptide Synthesis (doi: 10.1055/s-0036-1589055)
T. Kohiki#, Y. Kato#, Y. Nishikawa, K. Yorita, I. Sagawa, M. Denda, T. Inokuma, A. Shigenaga*, K. Fukui*, and A. Otaka* (#equal contribution)
Elucidation of inhibitor-binding pocket of D-amino acid oxidase using docking simulation and N-sulfanylethylanilide-based labeling technology
Org. Biomol. Chem. 2017, 15, 5289-5297. (doi: 10.1039/C7OB00633K) [徳島大学機関リポジトリ]
Inside Front Cover: Org. Biomol. Chem. 2017, 15, 5240. (doi: 10.1039/C7OB90109G)
T. Yoshimaru, K. Aihara, M. Komatsu, Y. Matsushita, Y. Okazaki, S. Toyokuni, J. Honda, M. Sasa, Y. Miyoshi, A. Otaka, and T. Katagiri*
Stapled BIG3 helical peptide ERAP potentiates antitumour activity for breast cancer therapeutics
Scientific Reports 7, Articlenumber:1821 (doi: 10.1038/s41598-017-01951-6)
T. Inokuma, T. Jichu, K. Nishida, A. Shigenaga, and A. Otaka*
A convenient method for preparation of α-imino carboxylic acid derivatives and application to the asymmetric synthesis of unnatural α-amino acid derivative
Chem. Pharm. Bull. 2017, 65, 573-581. (doi: 10.1248/cpb.c17-00158)
Highlighted paper selected by Editor-in-Chief
A. Yano, Y. Takahashi, H. Moriguchi, T. Inazumi, T. Koga, A. Otaka, and Y. Sugimoto*
An aromatic amino acid within intracellular loop 2 of the prostaglandin EP2 receptor is a prerequisite for selective association and activation of Gαs
BBA-Molecular and Cell Biology of Lipids 2017, 1862, 615-622. (doi: 10.1016/j.bbalip.2017.03.006)
2016
S. Tsuda, M. Mochizuki, K. Sakamoto, M. Denda, H. Nishio, A. Otaka and T. Yoshiya*
N-Sulfanylethylaminooxybutyramide (SEAoxy): A Crypto-Thioester Compatible with Fmoc Solid-Phase Peptide Synthesis
Org. Lett. 2016, 18, 5940–5943. (doi: 10.1021/acs.orglett.6b03055)
S. Mikawa, C. Mizuguchi, T. Baba, A. Shigenaga, T. Shimanouchi, A. Otaka, K. Akaji, and H. Saito*
Heparin promotes fibril formation of the N-terminal fragment of amyloidogenic aplipoprotein A-I
FEBS Lett. 2016, 590, 3492-3500. (doi: 10.1002/1873-3468.12426)
M. Eto#, N. Naruse#, K. Morimoto, K. Yamaoka, K. Sato, K. Tsuji, T. Inokuma, A. Shigenaga*, and A. Otaka* (#equal contribution)
Development of an anilide-type scaffold for the thioester precursor N-sulfanylethylcoumarinyl amide
Org. Lett. 2016, 18, 4416-4419. (doi: 10.1021/acs.orglett.6b02207)
T. Nakamura, K. Sato, N. Naruse, K. Kitakaze, T. Inokuma, T. Hirokawa, A. Shigenaga, K. Itoh, and A. Otaka*
Tailored synthesis of 162-residue S-monoglycosylated GM2-activator protein (GM2AP) analogues that allows access to protein library
ChemBioChem 2016, 17, 1986-1992. (doi: 10.1002/cbic.201600400)
Back Cover: ChemBioChem 2016, 17, 1994. (doi: 10.1002/cbic.201600521)
M. Denda, T. Morisaki, T. Kohiki, J. Yamamoto, K. Sato, I. Sagawa, T. Inokuma, Y. Sato, A. Yamauchi, A. Shigenaga*, and A. Otaka*
Labelling of endogenous target protein via N-S acyl transfer-mediated activation of N-sulfanylethylanilide
Org. Biomol. Chem. 2016, 14, 6244-6251. (doi: 10.1039/C6OB01014H)
Highlighted in Current Hot Articles in Organic & Biomolecular Chemistry
K. Kitakaze, Y. Mizutani, E. Sugiyama, C. Tasaki, D. Tsuji, N. Maita, T. Hirokawa, D. Asanuma, M. Kamiya, K. Sato, M. Setou, Y. Urano, T. Togawa, A. Otaka, H. Sakuraba, and K. Itoh*
Protease-resistant modified human β-hexosaminidase B ameliorates symptoms in GM2 gangliosidosis model
J. Clin. Invest. 2016, 126(5), 1691-1703. (doi: 10.1172/JCI85300)
T. Morisaki, M. Denda, J. Yamamoto, D. Tsuji, T. Inokuma, K. Itoh, A. Shigenaga*, and A. Otaka*
An N-Sulfanylethylanilide-based traceable linker for enrichment and selective labelling of target proteins
Chem. Commun. 2016, 52, 6911-6913. (doi: 10.1039/C6CC01229A) [徳島大学機関リポジトリ]
Y. Takechi-Haraya, R. Nadai, H. Kimura, K. Nishitsuji, K. Uchimura, K. Sakai-Kato, K. Kawakami, A. Shigenaga, T. Kawakami, A. Otaka, H. Hojo, N. Sakashita, and H. Saito*
Enthalpy-driven interactions with sulfated glycosaminoglycans promote cell membrane penetration of arginine peptides
Biochim. Biophys. Acta 2016, 1858, 1339-1349. (doi: 10.1016/j.bbamem.2016.03.021)
K. Aihara, K. Yamaoka, N. Naruse, T. Inokuma, A. Shigenaga, and A. Otaka*
One-pot/sequential native chemical ligation using photo-caged crypto-thioester
Org. Lett. 2016, 18(3), 596-599. (doi: 10.1021/acs.orglett.5b03661)
T. Shimizu, R. Miyajima, N. Naruse, K. Yamaoka, K. Aihara, A. Shigenaga*, and A. Otaka*
Facile preparation of peptides with C-terminal N-alkylamide via radical-initiated dethiocarboxylation
Chem. Pharm. Bull. 2016, 64, 375-378. (doi: 10.1248/cpb.c15-01025) [徳島大学機関リポジトリ]
T. Shimizu, R. Miyajima, K. Sato, K. Sakamoto, N. Naruse, M. Kita, A. Shigenaga*, and A. Otaka*
Facile synthesis of C-terminal peptide thioacids under mild conditions from N-sulfanylethylanilide peptides
Tetrahedron 2016, 72, 992-998. (doi: 10.1016/j.tet.2015.12.070) [徳島大学機関リポジトリ]
Y. Itoh, K. Aihara, P. Mellini, T. Tojo, Y. Ota, H. Tsumoto, V. R. Solomon, P. Zhan, M. Suzuki, D. Ogasawara, A. Shigenaga, T. Inokuma, H. Nakagawa, N. Miyata, T. Mizukami, A. Otaka*, and T. Suzuki*
Identification of SNAIL1 Peptide-Based Irreversible Lysine Specific Demethylase 1-Selective Inactivators
J. Med. Chem. 2016, 59, 1531-1544. (doi: 10.1021/acs.jmedchem.5b01323)
C. Komiya #, K. Aihara #, K. Morishita, H. Ding, T. Inokuma, A. Shigenaga, and A. Otaka* (# Equal contribution)
Development of an intein-inspired amide cleavage chemical device
J. Org. Chem. 2016, 81, 699-707. (doi: 10.1021/acs.joc.5b02399)
H. Kariyazono, R. Nadai, R. Miyajima, Y. Takechi-Haraya, T. Baba, A. Shigenaga, K. Okuhira, A. Otaka, and H. Saito*
Formation of stable nanodiscs by bihelical apolipoprotein A-I mimetic peptide
J. Pept. Sci. 2016, 22, 116-122. (doi: 10.1002/psc.2847)
R. Miyajima, Y. Tsuda, T. Inokuma, A. Shigenaga, M. Imanishi, S. Futaki, and A. Otaka*
Preparation of peptide thioesters from naturally occurring sequences using reaction sequence consisting of regioselective S-cyanylation and hydrazinolysis
Biopolymers (Peptide Science) 2016, 106, 531-546. (doi: 10.1002/bip.22757)
2015
C. Mizuguchi, F. Ogata, S. Mikawa, K. Tsuji, T. Baba, A. Shigenaga, T. Shimanouchi, K. Okuhira, A. Otaka, and H. Saito*
Amyloidogenic Mutation Promotes Fibril Formation of the N-terminal Apolipoprotein A-I on Lipid Membranes
J. Biol. Chem. 2015, 290, 20947-20959. (doi: 10.1074/jbc.M115.664227)
K. Tsuji, K. Tanegashima, K. Sato, K. Sakamoto, A. Shigenaga, T. Inokuma, T. Hara*, and A. Otaka*
Efficient one-pot synthesis of CXCL14 and its derivative using an N-sulfanylethylanilide peptide as a peptide thioester equivalent and their biological evaluation
Bioorg. Med. Chem. 2015, 23(17), 5909-5914. (doi: 10.1016/j.bmc.2015.06.064)
M. Kita, J. Yamamoto, T. Morisaki, C. Komiya, T. Inokuma, L. Miyamoto, K.Tsuchiya, A. Shigenaga*, and A. Otaka*
Design and synthesis of a hydrogen peroxide-responsive amino acid that induces peptide bond cleavage after exposure to hydrogen peroxide
Tetrahedron Lett. 2015, 56(28), 4228-4231. (doi: 10.1016/j.tetlet.2015.05.060) [徳島大学機関リポジトリ]
D. Jung, K. Sato, K. Min, A. Shigenaga, J. Jung, A. Otaka*, and Y. Kwon*
Photo-triggered fluorescent labelling of recombinant proteins in live cells
Chem. Commun. 2015, 51, 9670-9673. (doi: 10.1039/C5CC01067E)
K. Sato, K. Kitakaze, T. Nakamura, N. Naruse, K. Aihara, A. Shigenaga, T. Inokuma, D. Tsuji, K. Itoh, and A. Otaka*
The total chemical synthesis of monoglycosylated GM2 ganglioside activator using a novel cysteine surrogate
Chem. Commun. 2015, 51, 9946-9948. (doi: 10.1039/C5CC02967H)
K. Aihara, T. Inokuma, C. Komiya, A. Shigenaga, and A. Otaka*
Synthesis of lactam-bridged cyclic peptides by using sequential olefin metathesis and diimide reduction reactions
Tetrahedron 2015, 71, 4183-4191. (doi: 10.1016/j.tet.2015.04.093)
K. Takagi, H. Fukuda, S. Shuto, A. Otaka, and M. Arisawa*
Safe removal of the allyl protecting groups of allyl esters using a recyclable, low-leaching and ligand-free palladium nanoparticle Catalyst
Adv. Synth. Catal. 2015, 357(9), 2119-2124. (doi: 10.1002/adsc.201500055)
Y. Tsuda, A. Shigenaga, M. Denda, K. Sato, K. Kitakaze, T. Nakamura, T. Inokuma, K. Itoh, and A. Otaka*
Development of chemical methodology for preparation of peptide thioesters applicable to naturally occurring peptides using a sequential quadruple acyl transfer system
ChemistryOpen 2015, 4, 448-452. (doi: 10.1002/open.201500086)
T.Inokuma*, R. P. Fuller, and C. F. Barbas III
N-Sulfonyl-β-lactam hapten as an effective labeling reagent for aldolase mAb
Bioorg. Med. Chem. Lett. 2015, 25 (8), 1684–1687. (doi: 10.1016/j.bmcl.2015.03.011.)
M. Furutani, A. Uemura, A. Shigenaga, C. Komiya, A. Otaka, and K. Matsuura*
A Photoinduced growth system of peptide nanofibers addressed by DNA hybridization
Chem. Commun. 2015, 51, 8020-8022, and back cover. (doi: 10.1039/C5CC01452B and 10.1039/C5CC90206A)
Y. Takechi-Haraya, K. Tanaka, K. Tsuji, Y. Asami, H. Izawa, A. Shigenaga, A. Otaka, H. Saito, and K. Kawakami*
Molecular complex composed of β-cyclodextrin-grafted chitosan and pH-sensitive amphipathic peptide for enhancing cellular cholesterol efflux under acidic pH
Bioconjugate Chem. 2015, 26 (3), 572–581. (doi: 10.1021/acs.bioconjchem.5b00037)
K. Aihara, C. Komiya, A. Shigenaga, T. Inokuma, D. Takahashi, and A. Otaka*
Liquid-phase synthesis of bridged peptides using olefin metathesis of a protected peptide with a long aliphatic chain anchor
Org. Lett. 2015, 17(3), 696-699. (doi: 10.1021/ol503718j)
2014
N. Tsuji, M. Stadler, N. Kazumi, T. Inokuma, Y. Kobayashi, and Y. Takemoto*
Catalytic asymmetric synthesis of the pentacyclic core of (-)-nakadomarin A via oxazolidine as an iminium cation equivalent
Org. Biomol. Chem. 2014, 12, 7919-7922. (doi: 10.1039/C4OB01678E)
T. Azuma, A. Murata, Y. Kobayashi, T. Inokuma, and Y. Takemoto*
A dual arylboronic acid-aminothiourea catalytic system for the asymmetric intramolecular hetero-Michael reaction of α,β-unsaturated carboxylic acids
Org. Lett. 2014, 16(16), 4256–4259. (doi: 10.1021/ol501954r)
J. Yamamoto #, N. Maeda #, C. Komiya, T. Tanaka, M. Denda, K. Ebisuno, W. Nomura, H. Tamamura, Y. Sato, A. Yamauchi, A. Shigenaga*, and A. Otaka* (#Equal contribution)
Development of a fluoride-responsive amide bond cleavage device that is potentially applicable to a traceable linker
Tetrahedron 2014, 70, 5122-5127. (doi: 10.1016/j.tet.2014.05.110) [徳島大学機関リポジトリ]
J. Yamamoto, M. Denda, N. Maeda, M. Kita, C. Komiya, T. Tanaka, W. Nomura, H. Tamamura, Y. Sato, A. Yamauchi, A. Shigenaga*, and A. Otaka*
Development of a traceable linker containing a thiol-responsive amino acid for the enrichment and selective labelling of target proteins
Org. Biomol. Chem. 2014, 12, 3821-3826. (doi: 10.1039/C4OB00622D) [徳島大学機関リポジトリ]
K. Ebisuno, M. Denda, K. Ogura, T. Inokuma, A. Shigenaga*, and A. Otaka*
Development of caged non-hydrolyzable phosphoamino acids and application to photo-control of binding affinity of phosphopeptide mimetic to phosphopeptide-recognizing protein
Bioorg. Med. Chem. 2014, 22, 2984-2991. (doi: 10.1016/j.bmc.2014.04.002) [徳島大学機関リポジトリ]
E. Adachi, A. Kosaka, K. Tsuji, C. Mizuguchi, H. Kawashima, A. Shigenaga, K. Nagao, K. Akaji, A. Otaka, and H. Saito*
The extreme N-terminal region of human apolipoproteinA-I has a strong propensity to form amyloid fibrils
FEBS Lett. 2014, 588, 389-394. (doi: 10.1016/j.febslet.2013.11.031)
T. Nakamura, A. Shigenaga, K. Sato, Y. Tsuda, K. Sakamoto, and A. Otaka*
Examination of native chemical ligation using peptidyl prolyl thioester
Chem. Commun. 2014, 50, 58-60. (doi: 10.1039/C3CC47228K)
2013
K. Tanegashima#, K. Tsuji#, K. Suzuki, A. Shigenaga, A. Otaka, and T. Hara (#Equally contributed)
Dimeric peptides of the C-terminal region of CXCL14 function as CXCL12 inhibitors
FEBS Lett. 2013, 587, 3770-3775. (doi: 10.1016/j.febslet.2013.10.017)
K. Sato, A. Shigenaga, K. Kitakaze, K. Sakamoto, D. Tsuji, K. Itoh, and A. Otaka
Chemical Synthesis of Biologically Active Monoglycosylated GM2-activator Protein Analog Using N-Sulfanylethylanilide Peptide
Angew. Chem. Int. Ed. 2013, 52, 7855-7859. (doi: 10.1002/anie.201303390)
K. Tanegashima, K. Suzukia, Y. Nakayama, K. Tsuji, A. Shigenaga, A. Otaka, and T. Hara
CXCL14 is a natural inhibitor of the CXCL12-CXCR4 signaling axis
FEBS Lett. 2013, 587, 1731-1735. (doi: 10.1016/j.febslet.2013.04.046)
2012
K. Sakamoto, K. Sato, A. Shigenaga, K. Tsuji, S. Tsuda, H. Hibino, Y. Nishiuchi, and A. Otaka
Synthetic procedure for N-Fmoc amino acyl-N-sulfanylethylaniline linker as crypto-peptide thioester precursor with practical application to native chemical ligation
J. Org. Chem. 2012, 77, 6948-6958. (doi: 10.1021/jo3011107)
K. Ogura, A. Shigenaga, K. Ebisuno, H. Hirakawa, and A. Otaka
Fmoc-based solid phase synthesis of adenylylated peptides using diester-type adenylylated amino acid derivatives
Tetrahedron Lett. 2012, 53, 3429-3432. (doi: 10.1016/j.tetlet.2012.04.063)
A. Shigenaga, K. Ogura, H. Hirakawa, J. Yamamoto, K. Ebisuno, L. Miyamoto, K. Ishizawa, K. Tsuchiya, and A. Otaka
Development of reduction-responsive amino acid that induces peptide bond cleavage in hypoxic cells
ChemBioChem 2012, 13, 968-971. (doi: 10.1002/cbic.201200141) [徳島大学機関リポジトリ]
2011
H. Ding, A. Shigenaga, K.Sato, K. Morishita, and A. Otaka
Dual kinetically-controlled native chemical ligation using a combination of sulfanylproline and sulfanylethylanilide peptide
Org. Lett. 2011, 13, 5588-5591. (doi: 10.1021/ol202316v)
A. Shigenaga, K. Morishita, K. Yamaguchi, H. Ding, K. Ebisuno, K. Sato, J. Yamamoto, K. Akaji, and A. Otaka
Development of UV-responsive catch-and-release system of a cysteine protease model peptide
Tetrahedron 2011, 67, 8879-8886. (doi: 10.1016/j.tet.2011.09.062) [徳島大学機関リポジトリ]
K. Tsuji, A. Shigenaga, Y. Sumikawa, K. Tanegashima, K. Sato, K. Aihara, T. Hara, and A. Otaka
Application of N-C- or C-N-directed sequential native chemical ligation to the preparation of CXCL14 analogs and their biological evaluation
Bioorg. Med. Chem. 2011, 19, 4014-4020. (doi: 10.1016/j.bmc.2011.05.018)
K. Sato, A. Shigenaga, K. Tsuji, S. Tsuda, Y. Sumikawa, K. Sakamoto, and A. Otaka
N-Sulfanylethylanilide peptide as a crypto-thioester peptide
ChemBioChem 2011, 12, 1840-1844. (doi: 10.1002/cbic.201100241)
A. Shigenaga, H. Hirakawa, J. Yamamoto, K. Ogura, M. Denda, K. Yamaguchi, D. Tsuji, K. Itoh, and A. Otaka
Design and synthesis of caged ceramide: UV-responsive ceramide releasing system based on UV-induced amide bond cleavage followed by O-N acyl transfer
Tetrahedron 2011, 67, 3984-3990. (doi: 10.1016/j.tet.2011.04.048) [徳島大学機関リポジトリ]
2010
A. Shigenaga, J. Yamamoto, N. Nishioka, and A. Otaka
Enantioselective synthesis of stimulus-responsive amino acid via asymmetric α-amination of aldehyde
Tetrahedron 2010, 66, 7367-7372. (doi: 10.1016/j.tet.2010.07.033) [徳島大学機関リポジトリ]
Y. Nishikawa, Y. Takahara, S. Asada, A. Shigenaga, A. Otaka, K. Kitagawa, and T. Koide
A structure-activity relationship study elucidating the mechanism of sequence-specific collagen recognition by the chaperone HSP47
Bioorg. Med. Chem. 2010, 18, 3767-3775. (doi: 10.1016/j.bmc.2010.04.054)
A. Shigenaga, J. Yamamoto, Y. Sumikawa, T. Furuta, and A. Otaka
Development and photo-responsive peptide bond cleavage reaction of two-photon near-infrared excitation responsive peptide
Tetrahedron Lett. 2010, 51, 2868-2871. (doi: 10.1016/j.tetlet.2010.03.079) [徳島大学機関リポジトリ]
A. Shigenaga, Y. Sumikawa, S. Tsuda, K. Sato, and A. Otaka
Sequential native chemical ligation utilizing peptide thioacids derived from newly developed Fmoc-based synthetic method
Tetrahedron 2010, 66, 3290-3296. (doi: 10.1016/j.tet.2010.03.016)
A. Shigenaga, J. Yamamoto, H. Hirakawa, K. Ogura, N. Maeda, K. Morishita, and A. Otaka
Development of thiol-responsive amide bond cleavage device and its application for peptide nucleic acid-based DNA releasing system
Tetrahedron Lett. 2010, 51, 2525-2528. (doi: 10.1016/j.tetlet.2010.03.006) [徳島大学機関リポジトリ]
Y. Fujimoto, T. Shiraki, Y. Horiuchi, T. Waku, A. Shigenaga, A. Otaka, T. Ikura, K. Igarashi, S. Aimoto, S. Tate, and K. Morikawa
Proline cis/trans isomerase Pin1 regulates peroxisome proliferators-activated receptor gamma activity through the direct binding to the AF-1 domain
J. Biol. Chem. 2010, 285, 3126-3132. (doi: 10.1074/jbc.M109.055095)
2009
S.-M. Yun, T. Moulaei, D. Lim, J. K. Bang, J.-E. Park, S. R. Shenoy, F. Liu, Y. H. Kang, C. Liao, N.-K. Soung, S. Lee, D.-Y. Yoon, Y. Lim, D.-H. Lee, A. Otaka, E. Appella, J. B. McMahon, M. C. Nicklaus, T. R. Burke, Jr., M. B. Yaffe, A. Wlodawer, and K. S. Lee
Structural and functional analyses of minimal phosphopeptides targeting the polo-box domain of polo-like kinase 1
Nat. Struct. Mol. Biol. 2009, 16, 876-882. (doi: 10.1038/nsmb.1628)
Y. Yamaki, A. Shigenaga, K. Tomita, T. Narumi, N. Fujii, and A. Otaka
Synthesis of fluoroalkene dipeptide isosteres by intramolecular redox reaction utilizing N-heterocyclic carbenes (NHCs)
J. Org. Chem. 2009, 74, 3272-3277. [Featured Article] (doi: 10.10121/jo900134k)
Y. Yamaki, A. Shigenaga, J. Li, Y. Shimohigashi, and A. Otaka
Synthesis of amide-type fluoroalkene dipeptide isosteres by an intramolecular redox reaction
J. Org. Chem. 2009, 74, 3278-3285. [Featured Article] (doi: 10.10121/jo900135t)
S. Tsuda, A. Shigenaga, K. Bando, and A. Otaka
N→S Acyl-transfer-mediated synthesis of peptide thioesters using anilide derivatives
Org. Lett. 2009, 11, 823-826. (doi: 10.10121/ol8028093)
A. Shigenaga, J. Yamamoto, H. Hirakawa, K. Yamaguchi, and A. Otaka
FRET-based assay of the processing reaction kinetics of stimulus-responsive peptides: influence of amino acid sequence on reaction kinetics
Tetrahedron 2009, 65, 2212-2216. (doi: 10.1016/j.tet.2009.01.063) [徳島大学機関リポジトリ]
H. Nishikawa, S. Nakamura, E. Kodama, S. Ito, K. Kajiwara, K. Izumi, Y. Sakagami, S. Oishi, T. Ohkubo, Y. Kobayashi, A. Otaka, N. Fujii, and M. Matsuoka
Electrostatically constrained alpha-helical peptide inhibits replication of HIV-1 resistant to Enfuvirtide
Int. J. Biochem. Cell Biol. 2009, 41, 891-899. (doi: 10.1016/j.biocel.2008.08.039)
2008
H. Nishikawa, S. Oishi, M. Fujita, K. Watanabe, R. Tokiwa, H. Ohno, E. Kodama, K. Izumi, K. Kajiwara, T. Naitoh, M. Matsuoka, A. Otaka, and N. Fujii
Identification of minimal sequence for HIV-1 fusion inhibitors
Bioorg. Med. Chem. 2008, 16, 9184-9187. (doi: 10.1016/j.bmc.2008.09.018)
M. Ujike, H. Nishikawa, A. Otaka, N. Yamamoto, N. Yamamoto, M. Matsuoka, E. Kodama, N. Fujii, and F. Taguchi
Heptad Repeat-Derived Peptides Block Protease-Mediated Direct Entry from the Cell Surface of Severe Acute Respiratory Syndrome Coronavirus but Not Entry via the Endosomal Pathway
J. Virology 2008, 82, 588-592. (doi: 10.1128/JVI.01697-07)
2007
A. Shigenaga, D. Tsuji, N. Nishioka, S. Tsuda, K. Itoh and A. Otaka
Synthesis of a stimulus-responsive processing device and its application to a nucleocytoplasmic shuttle peptide
ChemBioChem 2007, 8, 1929-1931. (doi: 10.1002/cbic.200700442) [徳島大学機関リポジトリ]
Y. Sasaki, K. Yamaguchi, T. Tsuji, A. Shigenaga, N. Fujii and A. Otaka
Development of copper-mediated allylation of γ-activated-α,β-unsaturated lactam toward peptide mimetic synthesis
Tetrahedron Lett. 2007, 48, 3221-3224. (doi: 10.1016/j.tetlet.2007.03.017)
Y. Sasaki, A. Shigenaga, N. Fujii and A. Otaka
Synthesis of (Z)-alkene-containing cis-proline dipeptide mimetics using samarium(II) diiodide (SmI2)-mediated reductive alkylation reaction
Tetrahedron 2007, 63, 2000-2008. (doi: 10.1016/j.tet.2006.12.055)
2006
T. Narumi, A. Niida, K. Tomita, S. Oishi, A. Otaka, H. Ohno and N. Fujii
A novel one-pot reaction involving organocopper-mediated reduction/transmetalation/asymmetric alkylation, leading to the diastereoselective synthesis of functionalized (Z)-fluoroalkene dipeptide isosteres
Chem. Commun. 2006, 45, 4720-4722. (doi: 10.1039/b608596b)
Y. Sasaki, A. Niida, T. Tsuji, A. Shigenaga, N. Fujii, and A. Otaka
Stereoselective Synthesis of (Z)-Alkene-Containing Proline Dipeptide Mimetics
J. Org. Chem. 2006, 71, 4969-4979. (doi: 10.1021/jo060202z)
T. Koide, Y. Nishikawa, S. Asada, C. M. Yamazaki, Y. Takahara, D. L. Homma, A. Otaka, K. Ohtani, N. Wakamiya, K. Nagata, and K. Kitagawa
Specific recognition of the collagen triple helix by chaperone HSP47. II. The HSP47-binding structural motif in collagens and related proteins
J. Biol. Chem. 2006, 281, 11177-11185. (doi: 10.1074/jbc.M601369200)
A. Niida, M. Mizumoto, T. Narumi, E. Inokuchi, S. Oishi, H. Ohno, A. Otaka, K. Kitaura, and N. Fujii
Synthesis of (Z)-Alkene and (E)-Fluoroalkene-Containing Diketopiperazine Mimetics Utilizing Oraganocopper-Mediated Reduction-Alkylation and Diastereoselectivity Examination Using DFT Calculations
J. Org. Chem. 2006, 71, 4118-4129. (doi: 10.1021/jo060202z)
A. Niida, H. Tanigaki, E. Inokuchi, Y. Sasaki, S. Oishi, H. Ohno, H. Tamamura, Z. Wang, S. C. Peiper, K. Kitaura, A. Otaka, and N. Fujii
Stereoselective Synthesis of 3,6-Disubstituted-3,6-dihydropyridin-2-ones as Potential Diketopiperazine Mimetics Using Organocopper-Mediated anti-SN2' Reactions and Their Use in the Preparation of Low-Molecule CXCR4 Antagonists
J. Org. Chem. 2006, 71, 3942-3951. (doi: 10.1021/jo060390t)
M. Nakano, T. Hamada, T. Hayashi, S. Yonemitsu, L. Miyamoto, T. Toyoda, S. Tanaka, H. Masuzaki, K. Ebihara, Y. Ogawa, K. Hosoda, G. Inoue, Y. Yoshimasa, A. Otaka, T. Fushiki, and K. Nakao
a2 Isoform-specific activation of 5' adenosine monophosphate-activated protein kinase by 5-aminoimidazole-4-carboxamide-1-b-D-ribonucleoside at a physiological level activates glucose transport and increases glucose transporter 4 in mouse skeletal muscle
Metab. Clinic. Experiment. 2006, 55, 300-308. (doi: 10.1016/j.metabol.2005.09.003)
A. Niida, K. Tomita, M. Mizumoto, H. Tanigaki, T. Terada, S. Oishi, A. Otaka, K. Inui, and N. Fujii
Unequivocal Synthesis of (Z)-Alkene and (E)-Fluoroalkene Dipeptide Isosters to Probe Structural Requirements of Peptide Transporter PEPT1
Org. Lett. 2006, 8, 613-616. (doi: 10.1021/ol052781k)
S. Oishi, K. Miyamoto, A. Niida, M. Yamamoto, K. Ajito, H. Tamamura, A. Otaka, Y. Kuoroda, A. Asai, and N. Fujii
Application of Tri- and Tetrasubstituted Alkene Dipeptide Mimetics to Conformational Studies of Cyclic RGD Peptides
Tetrahedron 2006, 46, 1416-1424. (doi: 10.1016/j.tet.2005.11.033)
Y. Ohta, S. Itoh, A. Shigenaga, S. Shintaku, N. Fujii, and A. Otaka
Cysteine-derived S-Protected Oxazolidinones: Potential Chemical Devices for the Preparation of Peptide Thioesters
Org. Lett. 2006, 8, 467-470. (doi: 10.1021/ol052755m)
A. Niida, Z. Wang, K. Tomita, S. Oishi, H. Tamamura, A. Otaka, J.-M. Navenot, J. R. Broach, S. C. Peiper, and N. Fujii
Design and Synthesis of Downsized Metastin(45-54) Analogs with Maintenance of High GPR54 Agonistic Activity
Bioorg. Med. Chem. Lett. 2006, 16, 134-137. (doi: 10.1016/j.bmc.2005.09.054)
2005
H. Tamamura, A. Esaka, T. Ogawa, T. Araki, S. Ueda, Z. Wang, J. O. Trent, H. Tsutsumi, H. Masuno, H. Nakashima, N. Yamamoto, S. C. Peiper, A. Otaka, and N. Fujii
Structure-activity relationship studies on CXCR4 antagonists having cyclic pentapeptide scaffolds
Org. Biomol. Chem. 2005, 3, 4392-4394. (doi: 10.1039/b513145f)
S. Ueda, M. Fujita, H. Tamamura, N. Fujii, and A. Otaka
Photolabile Protection for One-Pot Sequential Native Chemical Ligation
ChemBioChem 2005, 6, 1983-1986. (doi: 10.1002/cbic.200500272)
H. Tamamura, A. Otaka, and N. Fujii
Development of anti-HIV agents targeting dynamic supramolecular mechanism: Entry and fusion inhibitors based on CXCR4/CCR5 antagonists and gp41-C34-remodeling peptides
Current HIV Res. 2005, 3, 289-301. (doi: 10.2174/157016205774370429)
H. Tamamura, T. Araki, S. Ueda, Z. Wang, S. Oishi, A. Esaka, J.O. Trent, H. Nakashima, N. Yamamoto, S.C. Peiper, A. Otaka, and N. Fujii
Identification of novel low molecular weight CXCR4 antagonists by structural tuning of cyclic tetrapeptide scaffolds
J. Med. Chem. 2005, 48, 3280-3289. (doi: 10.1021/jm050009h)
D. Nameki, E. Kodama, M. Ikeuchi, N. Mabuchi, A. Otaka, H. Tamamura, M. Ohno, N. Fujii, and M. Matsuoka
Mutations conferring resistance to human immunodeficiency virus type 1 fusion inhibitors are restricted by gp41 and Rev-responsive element functions
J. Virol. 2005, 79, 764-770. (doi: 10.1128/JVI.79.2.764-770.2005)
H. Tamamura, K. Hiramatsu, S. Ueda, Z. Wang, S. Kusano, S. Terakubo, J. O. Trent, S. C. Peiper, N. Yamamoto, H. Nakashima, A. Otaka, and N. Fujii
Stereoselective synthesis of [L-Arg-L/D-3-(2-naphthyl)alanine]-type (E)-alkene dipeptide isosteres and its application to the synthesis and biological evaluation of pseudopeptide analogues of the CXCR4 antagonist FC131
J. Med. Chem. 2005, 48, 380-391. (doi: 10.1021/jm049429h)
A. Niida, S. Oishi, Y. Sasaki, M. Mizumoto, H. Tamamura, N. Fujii, and A. Otaka
Facile access to (Z)-alkene-containing diketopiperazine mimetics utilizing organocopper-mediated anti-SN2' reactions
Tetrahedron Lett. 2005, 46, 4183-4186. (doi: 10.1016/j.tetlet.2005.04.057)
