Disulfide-Based Protecting Groups for the Cysteine Side Chain,Organic Letters

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Disulfide-Based Protecting Groups for the Cysteine Side Chain
Organic Letters ( IF 4.9 ) Pub Date : 2020-11-24 , DOI: 10.1021/acs.orglett.0c03705
Amit Chakraborty ₁ , Anamika Sharma _{1,

2} , Fernando Albericio _{1,

3,

4} , Beatriz G. de la Torre ₂

Affiliation

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 β-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.

中文翻译：

半胱氨酸侧链的基于二硫键的保护基

提出了两个新的基于二硫键的保护基（SIT和MOT）来取代S t Bu来取代Cys硫醇，这通常很难去除。两组均基于在β位具有支化点的仲硫醇，以有效调节其不稳定性和/或稳定性。这种独特的结构使它们与Fmoc / t Bu SPPS完全兼容。在合成结束时，这些基团可以直接用二硫苏糖醇和一些H ₂ O除去。

更新日期：2020-12-18

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