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Direct Fmoc-chemistry-based solid-phase synthesis of peptidyl thioesters.

ABSTRACT: Attachment of a growing peptide chain to a glycylaminomethyl resin via a thioglycinamide bond is compatible with Fmoc-chemistry solid-phase peptide synthesis. Subsequent S-alkylation of the thioamide gives a thioimide that, on treatment with aqueous trifluoroacetic acid, releases the peptide from the resin in the form of a C-terminal thioester.

SUBMITTER: Sharma I

PROVIDER: S-EPMC3184774 | biostudies-literature | 2011 Aug

REPOSITORIES: biostudies-literature

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Direct Fmoc-chemistry-based solid-phase synthesis of peptidyl thioesters.

Sharma Indrajeet I Crich David D

The Journal of organic chemistry 20110713 16

Attachment of a growing peptide chain to a glycylaminomethyl resin via a thioglycinamide bond is compatible with Fmoc-chemistry solid-phase peptide synthesis. Subsequent S-alkylation of the thioamide gives a thioimide that, on treatment with aqueous trifluoroacetic acid, releases the peptide from the resin in the form of a C-terminal thioester. ...[more]

PMID: 21718046

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