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通过环内裂解的异头化反应合成麦角硫因。

Mycothiol synthesis by an anomerization reaction through endocyclic cleavage.

作者信息

Manabe Shino, Ito Yukishige

机构信息

Synthetic Cellular Chemistry Lab, RIKEN, Hirosawa, Wako, Saitama 351-0198, Japan.

出版信息

Beilstein J Org Chem. 2016 Feb 22;12:328-33. doi: 10.3762/bjoc.12.35. eCollection 2016.

DOI:10.3762/bjoc.12.35
PMID:26977192
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4778527/
Abstract

Mycothiol is found in Gram-positive bacteria, where it helps in maintaining a reducing intracellular environment and it plays an important role in protecting the cell from toxic chemicals. The inhibition of the mycothiol biosynthesis is considered as a treatment for tuberculosis. Mycothiol contains an α-aminoglycoside, which is difficult to prepare stereoselectively by a conventional glycosylation reaction. In this study, mycothiol was synthesized by an anomerization reaction from an easily prepared β-aminoglycoside through endocyclic cleavage.

摘要

麦角硫因存在于革兰氏阳性菌中，它有助于维持细胞内的还原环境，并且在保护细胞免受有毒化学物质侵害方面发挥着重要作用。抑制麦角硫因的生物合成被认为是一种治疗结核病的方法。麦角硫因含有一种α-氨基糖苷，通过传统的糖基化反应很难立体选择性地制备。在本研究中，通过环内裂解，由一种易于制备的β-氨基糖苷经异头化反应合成了麦角硫因。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d9d4/4778527/d1e4b7632b39/Beilstein_J_Org_Chem-12-328-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d9d4/4778527/46b7628f6c4b/Beilstein_J_Org_Chem-12-328-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d9d4/4778527/127a6cebc2e9/Beilstein_J_Org_Chem-12-328-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d9d4/4778527/514099648c48/Beilstein_J_Org_Chem-12-328-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d9d4/4778527/603b36564e05/Beilstein_J_Org_Chem-12-328-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d9d4/4778527/19af28545cf1/Beilstein_J_Org_Chem-12-328-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d9d4/4778527/d1e4b7632b39/Beilstein_J_Org_Chem-12-328-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d9d4/4778527/46b7628f6c4b/Beilstein_J_Org_Chem-12-328-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d9d4/4778527/127a6cebc2e9/Beilstein_J_Org_Chem-12-328-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d9d4/4778527/514099648c48/Beilstein_J_Org_Chem-12-328-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d9d4/4778527/603b36564e05/Beilstein_J_Org_Chem-12-328-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d9d4/4778527/19af28545cf1/Beilstein_J_Org_Chem-12-328-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d9d4/4778527/d1e4b7632b39/Beilstein_J_Org_Chem-12-328-g007.jpg

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