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. 2011 Aug 19;76(16):6518-24.
doi: 10.1021/jo200497j. Epub 2011 Jul 13.

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

Indrajeet Sharma  1 , David Crich
Affiliations

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

Indrajeet Sharma et al. J Org Chem. .

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.

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Figures

Figure 1
Figure 1
1H-NMR spectra of H2N-l-Val-l-Ala-l-Phe-SBn (10) and its d-Phe diastereoisomer (11) in CDCl3 showing the extent of racemization (~22%) under the standard conditions.
Scheme 1
Scheme 1
Preparation of Fmoc-protected thioamides
Scheme 2
Scheme 2
Synthesis of diastereomeric tripeptidyl S-benzyl thioesters
Scheme 3
Scheme 3
Adaptation to the chlorotrityl resin
Scheme 4
Scheme 4
Synthesis of a methionine containing peptidyl thioester
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