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. in press.



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)



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 in press (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

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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



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)



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)




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



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




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)




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



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



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



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


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
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)
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)


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)


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)
Development of a fluoride-responsive amide bond cleavage device that is potentially applicable to a traceable linker
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).
Tetrahedron 2014, 70, 5122-5127. (doi:10.1016/j.tet.2014.05.110)
Development of a traceable linker containing a thiol-responsive amino acid for the enrichment and selective labelling of target proteins
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*.
Org. Biomol. Chem2014, 12, 3821-3826. (doi:10.1039/C4OB00622D)
Development of caged non-hydrolyzable phosphoamino acids and application to photo-control of binding affinity of phosphopeptide mimetic to phosphopeptide-recognizing protein
K. Ebisuno, M. Denda, K. Ogura, T. Inokuma, A. Shigenaga*, and A. Otaka*.
Bioorg. Med. Chem. 2014, 22, 2984-2991. (doi:10.1016/j.bmc.2014.04.002)
The extreme N-terminal region of human apolipoproteinA-I has a strong propensity to form amyloid fibrils
E. Adachi, A. Kosaka, K. Tsuji, C. Mizuguchi, H. Kawashima, A. Shigenaga, K. Nagao, K. Akaji, A. Otaka, and H. Saito*.
FEBS Lett. 2014, 588, 389-394. (doi: 10.1016/j.febslet.2013.11.031)


Examination of native chemical ligation using peptidyl prolyl thioester
T. Nakamura, A. Shigenaga, K. Sato, Y. Tsuda, K. Sakamoto, and A. Otaka*.
Chem. Commun. 2014, 50, 58-60. (doi:10.1039/C3CC47228K)


Dimeric peptides of the C-terminal region of CXCL14 function as CXCL12 inhibitors
K. Tanegashima#, K. Tsuji#, K. Suzuki, A. Shigenaga, A. Otaka, and T. Hara. (#Equally contributed) 
FEBS Lett. 2013, 587, 3770-3775.  (doi:10.1016/j.febslet.2013.10.017)