論文リスト

2018

A recyclable hydrophobic anchor-tagged asymmetric amino thiourea catalyst
T. Jichu #, T. Inokuma #, K. Aihara, T. Kohiki, K. Nishida, A. Shigenaga, K. Yamada, and A. Otaka*.  (#equal contribution)
ChemCatChem in press (doi: 10.1002/cctc.201800714)
 
 
Direct enantioselective indolylation of peptidyl imine for the synthesis of indolyl glycine-containing peptides
T. Inokuma, K. Nishida, A. Shigenaga, K. Yamada, and A. Otaka*.
Heterocycles (Professor Tomioka’s Special Issue) in press  (doi: 10.3987/COM-18-S(T)86)

 
 
Light-induced propulsion of a giant liposome driven by peptide nanofibre growth
H. Inaba*, A. Uemura, K. Morishita, T. Kohiki, A. Shigenaga, A. Otaka, and K. Matsuura*.
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
 
Resin-bound crypto-thioester for native chemical ligation
N. Naruse, K. Ohkawachi, T. Inokuma, A. Shigenaga, and A. Otaka*.
Org. Lett. 2018, 20, 2449-2453. (doi: 10.1021/acs.orglett.8b00795)
 
Effect of phosphatidylserine and cholesterol on membrane-mediated fibril formation by the N-terminal amyloidogenic fragment of apolipoprotein A-I
C. Mizuguchi, M. Nakamura, N. Kurimitsu, T. Ohgita, K. Nishitsuji, T. Baba, A. Shigenaga, T. Shimanouchi, K. Okuhira, A. Otaka, and H. Saito*.
Sci. Rep. 2018, 8, article number 5497. (doi: 10.1038/s41598-018-23920-3)
 
ProteoFind: A script for finding proteins that are suitable for chemical synthesis
A. Shigenaga*, N. Naruse, and A. Otaka.
Tetrahedron 2018, 74, 2291-2297. (doi: 10.1016/j.tet.2018.03.030)
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2017

Chemical synthetic platform for chlorpromazine oligomers that were reported as photo-degradation products of chlorpromazine
T. Kohiki, Y. Nishikawa, T. Inokuma, A. Shigenaga*, and A. Otaka*.
Chem. Pharm. Bull. 2017, 65, 1161-1166. (doi: 10.1248/cpb.c17-00692)

ChemPharmBull2017古曳

 

CXCL14 acts as a specific carrier of CpG into dendritic cells and activates Toll-like receptor 9-mediated adaptive immunity
K. Tanegashima*, R. Takahashi, H. Nuriya, N. Naruse, K. Tsuji, A. Shigenaga, A. Otaka, and T. Hara*.
EBioMedicine 2017, 24, 247-256. (doi: 10.1016/j.ebiom.2017.09.012)

Cysteine-free intramolecular ligaiton of N-sulfanylethylanilide peptide using 4-mercaptobenzylphosphonic acid: Synthesis of cyclic peptide, trichamide
K. Aihara, T. Inokuma, T. Jichu, Z. Lin, F. Fu, K. Yamaoka, A. Shigenaga, D. Hutchins, E. Schmidt, and A. Otaka*.
Synlett 2017, 28, 1944-1949. Cluster: Recent Advances in Protein and Peptide Synthesis  (doi: 10.1055/s-0036-1589055)

 

Elucidation of inhibitor-binding pocket of D-amino acid oxidase using docking simulation and N-sulfanylethylanilide-based labeling technology
T. Kohiki#, Y. Kato#, Y. Nishikawa, K. Yorita, I. Sagawa, M. Denda, T. Inokuma, A. Shigenaga*, K. Fukui*, and A. Otaka*. (#equal contribution)
Org. Biomol. Chem. 2017, 15, 5289-5297.  (doi: 10.1039/C7OB00633K)

Inside Front Cover: Org. Biomol. Chem. 2017, 15, 5240. (doi: 10.1039/C7OB90109G)

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Stapled BIG3 helical peptide ERAP potentiates antitumour activity for breast cancer therapeutics
T. Yoshimaru, K. Aihara, M. Komatsu, Y. Matsushita, Y. Okazaki, S. Toyokuni, J. Honda, M. Sasa, Y. Miyoshi, A. Otaka, and T. Katagiri*.
Scientific Reports 7, Article number: 1821 (doi: 10.1038/s41598-017-01951-6)

 

A convenient method for preparation of α-imino carboxylic acid derivatives and application to the asymmetric synthesis of unnatural α-amino acid derivative
T. Inokuma, T. Jichu, K. Nishida, A. Shigenaga, and A. Otaka*.
Chem. Pharm. Bull. 2017, 65, 573-581. (doi: 10.1248/cpb.c17-00158

Highlighted paper selected by Editor-in-Chief

ChemPharmBull 猪熊

 

An aromatic amino acid within intracellular loop 2 of the prostaglandin EP2 receptor is a prerequisite for selective association and activation of Gαs
A. Yano, Y. Takahashi, H. Moriguchi, T. Inazumi, T. Koga, A. Otaka, and Y. Sugimoto*.
BBA-Molecular and Cell Biology of Lipids 2017, 1862, 615-622. (doi: 10.1016/j.bbalip.2017.03.006

 

2016

N-Sulfanylethylaminooxybutyramide (SEAoxy): A Crypto-Thioester Compatible with Fmoc Solid-Phase Peptide Synthesis
S. Tsuda, M. Mochizuki, K. Sakamoto, M. Denda, H. Nishio, A. Otaka and T. Yoshiya*.
Org. Lett. 2016, 18, 5940–5943. (doi:10.1021/acs.orglett.6b03055)

 

Heparin promotes fibril formation of the N-terminal fragment of amyloidogenic aplipoprotein A-I
S. Mikawa, C. Mizuguchi, T. Baba, A. Shigenaga, T. Shimanouchi, A. Otaka, K. Akaji, and H. Saito*.
FEBS Lett. 2016, 590, 3492-3500. (doi: 10.1002/1873-3468.12426)

 

Development of an anilide-type scaffold for the thioester precursor N-sulfanylethylcoumarinyl amide
M. Eto#, N. Naruse#, K. Morimoto, K. Yamaoka, K. Sato, K. Tsuji, T. Inokuma, A. Shigenaga*, and A. Otaka*. (#equal contribution)
Org. Lett. 2016, 18, 4416-4419. (doi: 10.1021/acs.orglett.6b02207)
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Tailored synthesis of 162-residue S-monoglycosylated GM2-activator protein (GM2AP) analogues that allows access to protein library
T. Nakamura, K. Sato, N. Naruse, K. Kitakaze, T. Inokuma, T. Hirokawa, A. Shigenaga, K. Itoh, and A. Otaka*.
ChemBioChem 2016, 17, 1986-1992. (doi: 10.1002/cbic.201600400)

Back Cover: ChemBioChem 2016, 17, 1994. (doi: 10.1002/cbic.201600521)

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Labelling of endogenous target protein via N-S acyl transfer-mediated activation of N-sulfanylethylanilide
M. Denda, T. Morisaki, T. Kohiki, J. Yamamoto, K. Sato, I. Sagawa, T. Inokuma, Y. Sato, A. Yamauchi, A. Shigenaga*, and A. Otaka*.
Org. Biomol. Chem. 2016, 14, 6244-6251. (doi: 10.1039/C6OB01014H)

Highlighted in Current Hot Articles in Organic & Biomolecular Chemistry
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Protease-resistant modified human β-hexosaminidase B ameliorates symptoms in GM2 gangliosidosis model
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*.
J. Clin. Invest. 2016, 126(5), 1691-1703. (doi: 10.1172/JCI85300)

 

An N-Sulfanylethylanilide-based traceable linker for enrichment and selective labelling of target proteins
T. Morisaki, M. Denda, J. Yamamoto, D. Tsuji, T. Inokuma, K. Itoh, A. Shigenaga*, and A. Otaka*.
Chem. Commun. 2016, 52, 6911-6913. (doi: 10.1039/C6CC01229A)

Chem. Commun. morisaki2016.jpg

 

 

Enthalpy-driven interactions with sulfated glycosaminoglycans promote cell membrane penetration of arginine peptides
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*.
Biochim. Biophys. Acta 2016, 1858, 1339-1349. (doi: 10.1016/j.bbamem.2016.03.021)

 

One-pot/sequential native chemical ligation using photo-caged crypto-thioester
K. Aihara, K. Yamaoka, N. Naruse, T. Inokuma, A. Shigenaga, and A. Otaka*.
Org. Lett. 2016, 18(3), 596-599. (doi:10.1021/acs.orglett.5b03661

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Facile preparation of peptides with C-terminal N-alkylamide via radical-initiated dethiocarboxylation
T. Shimizu, R. Miyajima, N. Naruse, K. Yamaoka, K. Aihara, A. Shigenaga*, and A. Otaka*.
Chem. Pharm. Bull. 2016, 64, 375-378. (doi: 10.1248/cpb.c15-01025)

ShimizuCPB.jpg

 

 

Facile synthesis of C-terminal peptide thioacids under mild conditions from N-sulfanylethylanilide peptides
T. Shimizu, R. Miyajima, K. Sato, K. Sakamoto, N. Naruse, M. Kita, A. Shigenaga*, and A. Otaka*.
Tetrahedron 2016, 72, 992-998. (doi:10.1016/j.tet.2015.12.070

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Identification of SNAIL1 Peptide-Based Irreversible Lysine Specific Demethylase 1-Selective Inactivators
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*.
J. Med. Chem. 2016, 59, 1531-1544. (doi:10.1021/acs.jmedchem.5b01323

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Development of an intein-inspired amide cleavage chemical device
C. Komiya #, K. Aihara #, K. Morishita, H. Ding, T. Inokuma, A. Shigenaga, and A. Otaka*. (# Equal contribution)
J. Org. Chem. 2016, 81, 699-707. (doi:10.1021/acs.joc.5b02399
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Formation of stable nanodiscs by bihelical apolipoprotein A-I mimetic peptide
H. Kariyazono, R. Nadai, R. Miyajima, Y. Takechi-Haraya, T. Baba, A. Shigenaga, K. Okuhira, A. Otaka, and H. Saito*.
J. Pept. Sci. 2016, 22, 116-122. (doi:10.1002/psc.2847

 

Preparation of peptide thioesters from naturally occurring sequences using reaction sequence consisting of regioselective S-cyanylation and hydrazinolysis
R. Miyajima, Y. Tsuda, T. Inokuma, A. Shigenaga, M. Imanishi, S. Futaki, and A. Otaka*.
Biopolymers (Peptide Science) 2016, 106, 531-546. (doi:10.1002/bip.22757
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2015

Amyloidogenic Mutation Promotes Fibril Formation of the N-terminal Apolipoprotein A-I on Lipid Membranes
C. Mizuguchi, F. Ogata, S. Mikawa, K. Tsuji, T. Baba, A. Shigenaga, T. Shimanouchi, K. Okuhira, A. Otaka, and H. Saito*.
J. Biol. Chem. 2015, 290, 20947-20959. (doi:10.1074/jbc.M115.664227
 
Efficient one-pot synthesis of CXCL14 and its derivative using an N-sulfanylethylanilide peptide as a peptide thioester equivalent and their biological evaluation
K. Tsuji, K. Tanegashima, K. Sato, K. Sakamoto, A. Shigenaga, T. Inokuma, T. Hara*, and A. Otaka*.
Bioorg. Med. Chem. 2015, 23(17), 5909-5914. (doi:10.1016/j.bmc.2015.06.064
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Design and synthesis of a hydrogen peroxide-responsive amino acid that induces peptide bond cleavage after exposure to hydrogen peroxide
M. Kita, J. Yamamoto, T. Morisaki, C. Komiya, T. Inokuma, L. Miyamoto, K.Tsuchiya, A. Shigenaga*, and A. Otaka*.
Tetrahedron Lett.  2015, 56(28), 4228-4231. (doi: 10.1016/j.tetlet.2015.05.060)
 
Photo-triggered fluorescent labelling of recombinant proteins in live cells
D. Jung, K. Sato, K. Min, A. Shigenaga, J. Jung, A. Otaka*, and Y. Kwon*.
Chem. Commun. 2015, 51, 9670-9673. (doi: 10.1039/C5CC01067E)
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The total chemical synthesis of monoglycosylated GM2 ganglioside activator using a novel cysteine surrogate
K. Sato, K. Kitakaze, T. Nakamura, N. Naruse, K. Aihara, A. Shigenaga, T. Inokuma, D. Tsuji, K. Itoh, and A. Otaka*.
Chem. Commun. 2015, 51, 9946-9948. (doi: 10.1039/C5CC02967H)
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Synthesis of lactam-bridged cyclic peptides by using sequential olefin metathesis and diimide reduction reactions

K. Aihara, T. Inokuma, C. Komiya, A. Shigenaga, and A. Otaka*.

Tetrahedron 2015, 71, 4183-4191. (doi: 10.1016/j.tet.2015.04.093)

 

Safe removal of the allyl protecting groups of allyl esters using a recyclable, low-leaching and ligand-free palladium nanoparticle Catalyst

K. Takagi, H. Fukuda, S. Shuto, A. Otaka, and M. Arisawa*.

Adv. Synth. Catal. 2015, 357(9), 2119-2124. (doi: 10.1002/adsc.201500055)

 

 

Development of chemical methodology for preparation of peptide thioesters applicable to naturally occurring peptides using a sequential quadruple acyl transfer system

Y. Tsuda, A. Shigenaga, M. Denda, K. Sato, K. Kitakaze, T. Nakamura, T. Inokuma, K. Itoh, and A. Otaka*.

ChemistryOpen  2015, 4, 448-452. (doi: 10.1002/open.201500086)

 

 

N-Sulfonyl-β-lactam hapten as an effective labeling reagent for aldolase mAb
T.Inokuma*, R. P. Fuller, and C. F. Barbas III.

Bioorg. Med. Chem. Lett. 2015, 25 (8), 1684–1687. (doi: 10.1016/j.bmcl.2015.03.011.)

 


A Photoinduced growth system of peptide nanofibers addressed by DNA hybridization
M. Furutani, A. Uemura, A. Shigenaga, C. Komiya, A. Otaka, and K. Matsuura*.

Chem. Commun. 2015, 51, 8020-8022, and back cover. (doi: 10.1039/C5CC01452B and 10.1039/C5CC90206A)

 

 

Molecular complex composed of β-cyclodextrin-grafted chitosan and pH-sensitive amphipathic peptide for enhancing cellular cholesterol efflux under acidic pH
Y. Takechi-Haraya, K. Tanaka, K. Tsuji, Y. Asami, H. Izawa, A. Shigenaga, A. Otaka, H. Saito, and K. Kawakami*.

Bioconjugate Chem. 2015, 26 (3), 572–581. (doi: 10.1021/acs.bioconjchem.5b00037)

 

 

Liquid-phase synthesis of bridged peptides using olefin metathesis of a protected peptide with a long aliphatic chain anchor
K. Aihara, C. Komiya, A. Shigenaga, T. Inokuma, D. Takahashi, and A. Otaka*.
Org. Lett. 2015, 17(3), 696-699. (doi: 10.1021/ol503718j)

2014

Catalytic asymmetric synthesis of the pentacyclic core of (−)-nakadomarin A via oxazolidine as an iminium cation equivalent
N. Tsuji, M. Stadler, N. Kazumi, T. Inokuma, Y. Kobayashi, and Y. Takemoto*.
Org. Biomol. Chem. 2014, 12, 7919-7922. (doi:10.1039/C4OB01678E)

 
 
A dual arylboronic acid-aminothiourea catalytic system for the asymmetric intramolecular hetero-Michael reaction of α,β-unsaturated carboxylic acids
T. Azuma, A. Murata, Y. Kobayashi, T. Inokuma, and Y. Takemoto*.
Org. Lett. 2014, 16(16), 4256–4259. (doi:10.1021/ol501954r)