Chemo-enzymatic synthesis of a bioactive peptide containing a glutamine-linked oligosaccharide and its characterization

被引:43
作者
Haneda, K
Inazu, T
Mizuno, M
Iguchi, R
Tanabe, H
Fujimori, K
Yamamoto, K
Kumagai, H
Tsumori, K
Munekata, E
机构
[1] Noguchi Inst, Tokyo 1730003, Japan
[2] Kyoto Univ, Grad Sch Biostudies, Sakyo Ku, Kyoto 6068502, Japan
[3] Univ Tsukuba, Inst Appl Biochem, Tsukuba, Ibaraki 305, Japan
来源
BIOCHIMICA ET BIOPHYSICA ACTA-GENERAL SUBJECTS | 2001年 / 1526卷 / 03期
关键词
peptide; substance P; glutamine-linked oligosaccharide; endo-beta-N-acetylglucosaminidase; chemo-enzymatic synthesis;
D O I
10.1016/S0304-4165(01)00135-0
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A bioactive peptide containing a glutamine-linked oligosaccharide was chemo-enzymatically synthesized by use of the solid-phase method of peptide synthesis and the transglycosylation activity of endo-beta -N-acetylglucoeaminidase. Substance P, a neuropeptide, is an undecapeptide containing two L-glutamine residues. A substance P derivative with an N-acetyl-D-glucosamine residue attached to the fifth or sixth L-glutamine residue from the N-terminal region was chemically synthesized. A sialo complex-type oligosuccharide derived from a glycopeptide of hen egg yolk was added to the N-acetyl-D-glucosamine moiety of the substance P derivative using the transglycosylation activity of endo-beta -N-acetylglucosaminidase from Mucor hiemalis, and a substance P derivative with a sialo complex-type oligosaccharide attached to the L-glutamine residue was synthesized. This glycosylated substance P was biologically active. although the activity was rather low, and stable against peptidase digestion. The oligosaccharide moiety attached to the L-glutamine residue of the peptide was not liberated by peptide-N-4-(N-acetyl-beta -D-glucosaminyl) asparagine amidase F. (C) 2001 Elsevicr Science B.V. All rights reserved.
引用
收藏
页码:242 / 248
页数:7
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