Radical functionalization of thioglycosides in aqueous medium

被引：3
|
作者：
Kaur, Sarbjeet [1 ]
Luciano, Dominic P. [1 ,2 ]
Fan, Xinhao [1 ]
Zhao, Gaoyuan [1 ,3 ]
Messier, Sheridan [1 ]
Walker, Madison M. [1 ]
Zhang, Qiang [1 ]
Wang, Ting [1 ]
机构：
[1] SUNY Albany, Dept Chem, 1400 Washington Ave, Albany, NY 12222 USA
[2] Biogen, 115 Broadway, Cambridge, MA 02142 USA
[3] SUNY Stony Brook, Dept Chem, Stony Brook, NY 11794 USA
来源：
TETRAHEDRON LETTERS | 2021年 / 86卷
基金：
美国国家科学基金会;
关键词：
VISIBLE-LIGHT PHOTOCATALYSIS; THIOL-ENE REACTIONS; S-LINKED GLYCOPEPTIDES; PHOTOREDOX CATALYSIS; EOSIN-Y; CHEMISTRY; THIOOLIGOSACCHARIDES; GLYCOSYLATION; INITIATION; MECHANISM;
D O I：
10.1016/j.tetlet.2021.153499
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A visible-light-mediated thiol-ene reaction is successfully operated in aqueous medium. An organic photoredox catalyst (9-mesityl-10-methylacridinum tetrafluoroborate) is used to initiate the radical process to generate thiyl radicals upon light irradiation. Two reaction pathways were discovered in different aqueous buffer systems. A thiol-ene adduct is preferred in acidic reaction medium; while disulfide formation is found to be favored in basic reaction medium. The photocatalytic method is demonstrated to be applicable on unprotected peptides. (C) 2021 Elsevier Ltd. All rights reserved.
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页数：6
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