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.

引用

页数：6

共 50 条

[1] A one pot one step combined radical and ring-opening route for the dual functionalization of starch in aqueous medium
Meimoun, Julie
Wiatz, Vincent
Saint-Loup, Rene
Parcq, Julien
David, Adelina
Stoclet, Gregory
Gaucher, Valerie
Favrelle-Huret, Audrey
Bonnet, Fanny
Zinck, Philippe
CARBOHYDRATE POLYMERS, 2021, 254
[2] Mannich reaction of polysaccharides: Xylan functionalization in aqueous basic medium
Unlu, Cuneyt H.
Kutlu, Meltem
Atici, Oya Galioglu
CARBOHYDRATE POLYMERS, 2015, 127 : 19 - 27
[3] The utility of indium in aqueous medium radical reactions
Miyabe, H
Naito, T
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (09) : 1267 - 1270
[4] Carbon-Hydrogen Bond Functionalization in Aqueous Medium: A Brief Review
Sarkar, Rajib
Mukhopadhyay, Chhanda
CURRENT GREEN CHEMISTRY, 2019, 6 (03) : 184 - 197
[5] Oxidative degradation of fensulfothion by hydroxyl radical in aqueous medium
Paul, M. M. Sunil
Aravind, Usha K.
Pramod, G.
Aravindakumar, C. T.
CHEMOSPHERE, 2013, 91 (03) : 295 - 301
[6] A novel and efficient alkyl radical trap in aqueous medium
Barton, DHR
Jacob, M
Peralez, E
TETRAHEDRON LETTERS, 1999, 40 (52) : 9201 - 9204
[7] Reactivity of Nucleosides with a Hydroxyl Radical in Non-aqueous Medium
Rodriguez-Muniz, Gemma M.
Luisa Marin, M.
Lhiaubet-Vallet, Virginie
Miranda, Miguel A.
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (26) : 8024 - 8027
[8] Aqueous medium radical addition to ketimines with a phenolic hydroxyl group
Miyabe, H
Yamaoka, Y
Takemoto, Y
SYNLETT, 2004, (14) : 2597 - 2599
[9] Radical-based alkylation of guanine derivatives in aqueous medium
Chatgilialoglu, Chryssostomos
Caminal, Clara
Mulazzani, Quinto G.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (09) : 3494 - 3498
[10] Radical functionalization of allenes
Yi, Rongnan
Li, Qiang
Xie, Long-Yong
Wei, Wen-Ting
CHEMICAL COMMUNICATIONS, 2025,

← 1 2 3 4 5 →