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Org Lett. 2010 Apr 16;12(8):1852-5. doi: 10.1021/ol100471k.

Direct conversion of resin-bound peptides to C-terminal esters.

Author information

1
Department of Chemistry and Biochemistry, University of California at Santa Cruz, 1156 High Street, Santa Cruz, California 95064, USA.

Abstract

A mild and effective method was developed to convert peptides immobilized on the 2-chlorotrityl and Wang resins directly to C-terminal esters. After conventional Fmoc peptide synthesis, treatment with anhydrous HCl (0.2-3 M) in a variety of alcohols was shown to produce the corresponding peptide esters in good yield and purity. Under the mildest conditions investigated, acid-sensitive protection groups such as N-Boc, trityl, tert-butyl ether, tert-butyl ester, and Pbf remain intact.

PMID:
20329782
DOI:
10.1021/ol100471k
[Indexed for MEDLINE]

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