来自大鼠肾小球基底膜的致肾炎糖肽。X. N-三糖基二肽的合成及其顺反异构体的特性。

The nephritogenic glycopeptide from rat glomerular basement membrane. X. Synthesis of an N-triglycosyl dipeptide and characteristics of its cis-trans isomers.

作者信息

Takeda T, Kojima K, Ogihara Y

机构信息

Faculty of Pharmaceutical Sciences, Nagoya City University, Japan.

出版信息

Chem Pharm Bull (Tokyo). 1991 Oct;39(10):2699-701. doi: 10.1248/cpb.39.2699.

DOI:10.1248/cpb.39.2699

PMID:1806293

Abstract

Isomers of O-alpha-D-glucopyranosyl-(1----6)-O-beta-D-glucopyranosyl- (1----6)-N-[L-aspart-1-oyl-(L-proline)-4-oyl]-alpha-D-glucopyranos ylamine have been prepared, as models for a derivative possibly present in the glomerular basement membrane of rats, by condensation of the corresponding dipeptide derivative (5) with triglycosylamine (4) in the presence of O,O-diethylcyanophosphonate, followed by deprotection of the trisaccharide-dipeptide derivative. During the deprotection process, cis- and trans-isomers containing proline were separated by silica gel column chromatography and also reversed-phase high performance liquid chromatography.

摘要

已制备出O-α-D-吡喃葡萄糖基-(1→6)-O-β-D-吡喃葡萄糖基-(1→6)-N-[L-天冬氨酰-(L-脯氨酸)-4-酰基]-α-D-吡喃葡萄糖胺的异构体，作为可能存在于大鼠肾小球基底膜中的一种衍生物的模型，方法是在O,O-二乙基氰基膦酸酯存在下，使相应的二肽衍生物(5)与三糖基胺(4)缩合，随后对三糖-二肽衍生物进行脱保护。在脱保护过程中，通过硅胶柱色谱法以及反相高效液相色谱法分离出含脯氨酸的顺式和反式异构体。