Novel methodology for the solid-phase synthesis of phosphinic peptides

被引：23

作者：

Buchardt, J ^{[1
]}

Meldal, M ^{[1
]}

机构：

[1] Carlsberg Lab, Dept Chem, DK-2500 Valby, Denmark

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 19期

关键词：

D O I：

10.1039/b003848m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel. versatile strategy for the solid phase synthesis of phosphinic peptides is developed in which the phosphorus- carbon bond is formed on a polymer support during peptide synthesis. The formation of bis(trimethylsilyl) 1-(allyloxy-carbonylamino)ethylphosphonite from 1-(allyloxycarbonylamino)ethylphosphinic acid is investigated, as well as the Michael addition of the former to a resin-bound acrylate. Conditions are also established for the clean, quantitative conversion of a resin-bound, N-terminus acryloylated peptide with bis(trimethylsilyl) 1-(allyloxycarbonylamino)ethylphosphonite. Conventional peptide synthesis is then employed to obtain a phosphinic undecapeptide in high yield and purity.

引用

页码：3306 / 3310

页数：5

共 23 条

[1] RENIN INHIBITORS - SYNTHESIS OF TRANSITION-STATE ANALOG INHIBITORS CONTAINING PHOSPHORUS-ACID DERIVATIVES AT THE SCISSILE BOND [J].