四氢吡喃基，一种用于Fmoc肽化学的非芳香族酸不稳定型半胱氨酸保护基团。

Tetrahydropyranyl, a nonaromatic acid-labile Cys protecting group for Fmoc peptide chemistry.

作者信息

Ramos-Tomillero Iván, Rodríguez Hortensia, Albericio Fernando

机构信息

†Institute for Research in Biomedicine, 08028 Barcelona, Spain.

‡Department of Organic Chemistry, University of Barcelona, 08028 Barcelona, Spain.

出版信息

Org Lett. 2015 Apr 3;17(7):1680-3. doi: 10.1021/acs.orglett.5b00444. Epub 2015 Mar 12.

DOI:10.1021/acs.orglett.5b00444

PMID:25764355

Abstract

Tetrahydropyranyl (Thp), which exploits the concept of being an S,O-acetal nonaromatic protecting group for cysteine, has been shown to be superior to Trt, Dpm, Acm, and StBu in solid-phase peptide synthesis using the Fmoc/tBu strategy. Thus, Cys racemization and C-terminal 3-(1-piperidinyl)alanine formation were minimized when the Cys was protected with Thp. This nonaromatic protecting group also improved the solubility of Cys-containing protected peptides.

摘要

四氢吡喃基（Thp）利用了作为半胱氨酸的S，O-缩醛非芳香族保护基团的概念，在使用Fmoc/tBu策略的固相肽合成中，已被证明优于Trt、Dpm、Acm和StBu。因此，当半胱氨酸用Thp保护时，半胱氨酸消旋化和C端3-（1-哌啶基）丙氨酸的形成被最小化。这种非芳香族保护基团还提高了含半胱氨酸的保护肽的溶解度。