Disulfide-Based Protecting Groups for the Cysteine Side Chain

被引：21

作者：

Chakraborty, Amit ^{[1
]}

Sharma, Anamika ^{[1
,2
]}

Albericio, Fernando ^{[1
,3
,4
,5
]}

de la Torre, Beatriz G. ^{[2
]}

机构：

[1] Univ KwaZulu Natal, Sch Chem & Phys, Peptide Sci Lab, ZA-4001 Durban, South Africa

[2] Univ KwaZulu Natal, Coll Hlth Sci, Sch Lab Med & Med Sci, KwaZulu Natal Res Innovat & Sequencing Platform K, ZA-4041 Durban, South Africa

[3] Inst Adv Chem Catalonia IQAC CSIC, Barcelona 08034, Spain

[4] Univ Barcelona, CIBER BBN, Networking Ctr Bioengn Biomat & Nanomed, Barcelona 08028, Spain

[5] Univ Barcelona, Dept Organ Chem, Barcelona 08028, Spain

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 24期

基金：

新加坡国家研究基金会;

关键词：

PEPTIDES;

D O I：

10.1021/acs.orglett.0c03705

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two new disulfide-based protecting groups (SIT and MOT) are proposed for Cys thiol in the substitution of StBu, which is often difficult to remove. Both groups are based on a secondary thiol with a branched point in the beta-position for an efficient modulation of its lability and/or stability. This unique structure allows them to be fully compatible with Fmoc/tBu SPPS. At the end of the synthesis, these groups are removed in a straightforward manner with dithiothreitol with some H2O.

引用

页码：9644 / 9647

页数：4

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