Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, New York 10065, United States.
J Am Chem Soc. 2011 Feb 9;133(5):1597-602. doi: 10.1021/ja110115a. Epub 2011 Jan 5.
Described herein is a method for the joining of complex peptides to complex oligosaccharides via an N-linkage. The ω-aspartylation is conducted by coupling fully deprotected glycosylamine with a peptide containing a unique thioacid at the ω-aspartate carboxyl. In the presence of HOBT, under conditions that, in principle, allow for oxidation, complex components are combined in encouraging yields to produce structurally and stereochemically defined N-linked glycopolypeptides wherein the carbohydrate domain can be quite complex. Various mechanisms for oxidative coupling are proposed.
本文描述了一种通过 N-连接将复杂肽与复杂寡糖连接的方法。ω-天冬酰胺酰化是通过将完全脱保护的糖胺与含有独特巯基酸的肽在 HOBT 存在下偶联来进行的,在原则上允许氧化的条件下,以令人鼓舞的产率组合复杂成分,以产生结构和立体化学定义明确的 N-连接糖多肽,其中碳水化合物结构域可以非常复杂。提出了各种氧化偶联机制。