Dynamic Cyclic Thiodepsipeptide Libraries From Thiol-Thioester Exchange

Thiol−thioester exchange was found to readily generate libraries of cyclic thiodepsipeptides under thermodynamic control, which will enable their use in a variety of dynamic combinatorial chemistry assays. The kinetic determinants of macrocycle formation and the role of amino acid structure on the r...

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Published in:Organic letters 2010-04, Vol.12 (8), p.1860-1863
Main Authors: Ghosh, Soumyadip, Ingerman, Lindsey A, Frye, Aaron G, Lee, Stephen J, Gagné, Michel R, Waters, Marcey L
Format: Article
Language:English
Subjects:
Combinatorial Chemistry Techniques
Depsipeptides - chemistry
Esters - chemistry
Kinetics
Peptides, Cyclic - chemistry
Sulfhydryl Compounds - chemistry
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cited_by cdi_FETCH-LOGICAL-a380t-e57778551f83a7a5b631b96839c09973baf734ff85571ba636be64d4cfb0e8173
cites cdi_FETCH-LOGICAL-a380t-e57778551f83a7a5b631b96839c09973baf734ff85571ba636be64d4cfb0e8173
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creator Ghosh, Soumyadip
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description Thiol−thioester exchange was found to readily generate libraries of cyclic thiodepsipeptides under thermodynamic control, which will enable their use in a variety of dynamic combinatorial chemistry assays. The kinetic determinants of macrocycle formation and the role of amino acid structure on the reaction dynamics are discussed.
doi_str_mv 10.1021/ol1004752
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source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Combinatorial Chemistry Techniques
Depsipeptides - chemistry
Esters - chemistry
Kinetics
Peptides, Cyclic - chemistry
Sulfhydryl Compounds - chemistry
title Dynamic Cyclic Thiodepsipeptide Libraries From Thiol-Thioester Exchange
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