Solid-Phase Synthesis of Peptidyl Thioacids Employing a 9-Fluorenylmethyl Thioester-Based Linker in Conjunction with Boc Chemistry

被引：14

作者：

Crich, David ^{[1
,2
]}

Sana, Kasinath ^{[2
]}

机构：

[1] CNRS, Inst Chim Subst Nat, Ctr Rech Gif Sur Yvette, F-91198 Gif Sur Yvette, France

[2] Wayne State Univ, Dept Chem, Detroit, MI 48202 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 19期

关键词：

TOTAL CHEMICAL-SYNTHESIS; FMOC-BASED SYNTHESIS; PROTEIN-SYNTHESIS; ALPHA-THIOESTERS; CYCLIC-PEPTIDES; SULFONYL AZIDES; BAL STRATEGY; THIO ACIDS; AMINO-ACID; LIGATION;

D O I：

10.1021/jo901218g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for the synthesis of peptidyl thioacids is described on the basis of the use of the N-[9-(thiometliyl)-9H-fluoren-2-yl]succinamic acid and cross-linked aminomethyl polystyrene resin. The method employs standard Boc chemistry SPPS techniques in conjunction with 9-fluorenyl-methyloxycarbonyl protection of side-chain alcohols and amines and 9-fluorenylmethyl protection of side-chain acids and thiols. Cleavage from the resin is accomplished with piperidine, which also serves to remove the side-chain protection and avoids the HF conditions usually associated with the resin cleavage stage of Boc chemistry SPPS. The so-obtained thioacids are converted to simple thioesters in high yield by standard alkylation according to well-established methods.

引用

页码：7383 / 7388

页数：6