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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Bibliographic Details
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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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol1004752