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使用S-叔丁基巯基残基进行硫醇保护合成(LysA13)牛胰岛素A链类似物作为(Lys(Tfa)A13)A(SO3H)4和Nα-A1-Msc-(LysA13)A(SO3H)4衍生物(作者译)

[Synthesis of (LysA13)bovine insulin A chain analogs as (Lys(Tfa)A13)A(SO3H)4 and Nalpha-A1-Msc-(LysA13)A(SO3H)4 derivatives using the S-tert-butylmercapto residue for thiol protection (author's transl)].

作者信息

Wolf G, Berndt H, Brandenburg D

出版信息

Hoppe Seylers Z Physiol Chem. 1979 Nov;360(11):1569-78.

PMID:574493
Abstract

The following paper describes the synthesis of the [LysA13]bovine insulin A chain analog as [Lys(Tfa)A13]A(SO3H)4 and NalphaA1-Msc-[LysA13]A(SO3H)4 derivatives using the S-tert-butylmercapto residue for thiol protection. Although the intermediate S-tert-butylmercaptocysteinyl-peptide derivatives showed a good solubility in organic solvents the resulting fully protected A chain derivatives had a poor solubility in organic solvents and therefore were deblocked converted into the tetra(S-sulfonic acid) derivatives and purified via ionexchange chromatography.

摘要

以下论文描述了使用S-叔丁基巯基残基进行硫醇保护,将[LysA13]牛胰岛素A链类似物合成为[Lys(Tfa)A13]A(SO3H)4和NαA1-Msc-[LysA13]A(SO3H)4衍生物的过程。尽管中间体S-叔丁基巯基半胱氨酰肽衍生物在有机溶剂中表现出良好的溶解性,但所得的完全保护的A链衍生物在有机溶剂中的溶解性较差,因此进行脱保护,转化为四(S-磺酸)衍生物,并通过离子交换色谱法进行纯化。

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