Issue 10, 2008
From the journal:

Organic & Biomolecular Chemistry

Application of a novel thioesterification reaction to the synthesis of chemokine CCL27 by the modified thioester method

Hironobu Hojo,*a   Yuichi Murasawa,a   Hidekazu Katayama,a   Tsuyoshi Ohira,b   Yuko Nakaharaa  and  Yoshiaki Nakahara*a  

* Corresponding authors

a Department of Applied Biochemistry, Institute of Glycotechnology, Tokai University, Hiratsuka, Kanagawa, Japan
E-mail: hojo@keyaki.cc.u-tokai.ac.jp, yonak@keyaki.cc.u-tokai.ac.jp
Fax: +81 463 50 2075
Tel: +81 463 58 1211

b Department of Biological Sciences, Faculty of Science, Kanagawa University, Hiratsuka, Kanagawa, Japan
E-mail: ohirat-bio@kanagawa-u.ac.jp
Fax: +81 463 58 9684
Tel: +81 463 59 4111

Abstract

Aryl thioesters of peptide segments were prepared by the conventional 9-fluorenylmethoxycarbonyl (Fmoc) strategy using a novel N-alkyl cysteine (NAC)-assisted thioesterification reaction. The peptide carrying NAC at its C-terminus was prepared by the Fmoc strategy and converted to the aryl thioester by 4-mercaptophenylacetic acid (MPAA) treatment without significant side reactions. The peptide thioester was used for the efficient preparation of 95-amino acid (AA) chemokine CCL27 by an Ag+-free thioester method.

Graphical abstract: Application of a novel thioesterification reaction to the synthesis of chemokine CCL27 by the modified thioester method

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Article information

DOI
https://doi.org/10.1039/B800884A
Article type
Paper
Submitted
17 Jan 2008
Accepted
03 Mar 2008
First published
31 Mar 2008

Org. Biomol. Chem., 2008,6, 1808-1813

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Application of a novel thioesterification reaction to the synthesis of chemokine CCL27 by the modified thioester method

H. Hojo, Y. Murasawa, H. Katayama, T. Ohira, Y. Nakahara and Y. Nakahara, Org. Biomol. Chem., 2008, 6, 1808 DOI: 10.1039/B800884A

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