通过Boc策略合成糖基化肽硫酯及其在片段缩合中的应用。

Synthesis of a glycosylated peptide thioester by the Boc strategy and its application to segment condensation.

作者信息

Haginoya Eiichiro, Hojo Hironobu, Nakahara Yuko, Nakahara Yoshiaki, Nabeshima Kazuki, Toole Bryan P, Watanabe Yasushi

机构信息

Department of Applied Biochemistry, Institute of Glycotechnology, Tokai University, Kanagawa.

出版信息

Biosci Biotechnol Biochem. 2006 Jun;70(6):1338-49. doi: 10.1271/bbb.50621.

DOI:10.1271/bbb.50621

PMID:16794312

Abstract

The synthesis of a chitobiosylated peptide thioester by the t-butoxycarbonyl (Boc) strategy is demonstrated. Boc-Asn carrying benzyl-protected chitobiose was introduced during application of the Boc mode solid-phase method. HF treatment of the resulting protected peptide resin gave the desired chitobiosylated peptide thioester. This thioester was used to prepare the peptide sequence derived from extracellular matrix metalloproteinase inducers (emmprin) (34-94), (34-118) and (22-118) by the thioester segment condensation method. The conformation of these glycopeptides is characterized by circular dichroism (CD) spectral measurement.

摘要

本文展示了通过叔丁氧羰基（Boc）策略合成壳二糖基化肽硫酯的方法。在应用Boc模式固相法的过程中引入了携带苄基保护壳二糖的Boc-Asn。对所得的保护肽树脂进行HF处理，得到了所需的壳二糖基化肽硫酯。该硫酯通过硫酯片段缩合方法用于制备源自细胞外基质金属蛋白酶诱导剂（胞外基质金属蛋白酶诱导因子，emmprin）的肽序列（34-94）、（34-118）和（22-118）。通过圆二色性（CD）光谱测量对这些糖肽的构象进行了表征。