Application of a novel thioesterification reaction to the synthesis of chemokine CCL27 by the modified thioester method.
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.
Hojo
Hironobu
H
Department of Applied Biochemistry, Institute of Glycotechnology, Tokai University, Hiratsuka, Kanagawa 259-1292, Japan. hojo@keyaki.cc.u-tokai.ac.jp
Murasawa
Yuichi
Y
Katayama
Hidekazu
H
Ohira
Tsuyoshi
T
Nakahara
Yuko
Y
Nakahara
Yoshiaki
Y
D000595:Amino Acid Sequence; D054425:Chemokine CCL27 / Q000138:chemical synthesis* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D004220:Disulfides / Q000737:chemistry; D004952:Esters / Q000737:chemistry*; D008969:Molecular Sequence Data; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D054425:Chemokine CCL27; D004220:Disulfides; D004952:Esters; D013438:Sulfhydryl Compounds