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

Hironobu Hojo; Yuichi Murasawa; Hidekazu Katayama; Tsuyoshi Ohira; Yuko Nakahara; Yoshiaki Nakahara

doi:10.1039/b800884a

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

Hironobu Hojo, Yuichi Murasawa, Hidekazu Katayama, Tsuyoshi Ohira, Yuko Nakahara, Yoshiaki Nakahara

Research output: Contribution to journal › Article › peer-review

54 Scopus citations

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.

Original language	English
Pages (from-to)	1808-1813
Number of pages	6
Journal	Organic and Biomolecular Chemistry
Volume	6
Issue number	10
DOIs	https://doi.org/10.1039/b800884a
State	Published - 2008
Externally published	Yes

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title = "Application of a novel thioesterification reaction to the synthesis of chemokine CCL27 by the modified thioester method",

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.",

author = "Hironobu Hojo and Yuichi Murasawa and Hidekazu Katayama and Tsuyoshi Ohira and Yuko Nakahara and Yoshiaki Nakahara",

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doi = "10.1039/b800884a",

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T1 - Application of a novel thioesterification reaction to the synthesis of chemokine CCL27 by the modified thioester method

AU - Hojo, Hironobu

AU - Murasawa, Yuichi

AU - Katayama, Hidekazu

AU - Ohira, Tsuyoshi

AU - Nakahara, Yuko

AU - Nakahara, Yoshiaki

PY - 2008

Y1 - 2008

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/43049120006

U2 - 10.1039/b800884a

DO - 10.1039/b800884a

M3 - 記事

C2 - 18452017

AN - SCOPUS:43049120006

SN - 1477-0520

VL - 6

SP - 1808

EP - 1813

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 10

ER -

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

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