Non-enzymatic reaction of glycosyl oxazoline with peptides

被引：12

作者：

Wang, Ning ^{[1
,2
,3
]}

Seko, Akira ^{[2
]}

Daikoku, Shusaku ^{[2
]}

Kanie, Osamu ^{[2
,4
]}

Takeda, Yoichi ^{[2
,5
]}

Ito, Yukishige ^{[1
,2
]}

机构：

[1] RIKEN, Synthet Cellular Chem Lab, 2-1 Hirosawa, Wako, Saitama 3510198, Japan

[2] Sci & Technol Agcy JST, ERATO Ito Glycotril Project, 2-1 Hirosawa, Wako, Saitama 3510198, Japan

[3] Jiangnan Univ, Key Lab Carbohydrate Chem & Biotechnol, Minist Educ, Sch Biotechnol, 1800 Lihu Ave, Wuxi 214122, Peoples R China

[4] Tokai Univ, Inst Glycosci, 4-1-1 Kitakaname, Hiratsuka, Kanagawa 2591292, Japan

[5] Ritsumeikan Univ, Dept Biotechnol, Shiga 5258577, Japan

来源：

CARBOHYDRATE RESEARCH | 2016年 / 436卷

关键词：

Oxazoline; Chemical ligation; Acetamidine; Lysine; CHEMOENZYMATIC SYNTHESIS; GLYCOPROTEINS; DERIVATIVES; CANCER;

D O I：

10.1016/j.carres.2016.11.002

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：

Recently, a number of chemoenzymatic strategies have been explored for achieving preparation of homogeneous glycopeptides and glycoproteins, especially by using endoglycanases and glycosyl oxazolines. However, concomitant occurrence of non-enzymatic reactions has been reported, but no further characterization of the byproducts was conducted. In this work, we made an attempt to identify the side product by using model substrates. Analysis of the product allowed us to propose that the oxazoline ring was attacked by the amino group of lysine, leading to the formation of disubstituted acetamidine. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：31 / 35

页数：5

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