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Synfacts 2010(7): 0843-0843  
DOI: 10.1055/s-0029-1220096
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Direct Conversion of Resin-Bound Peptides into C-Terminal Esters

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Maki Minakawa
R. A. Turner, R. J. Weber, R. S. Lokey*
University of California at Santa Cruz, USA
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Publication History

Publication Date:
22 June 2010 (online)

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Significance

A mild and effective method for the direct conversion of resin-bound peptides into C-terminal esters was developed. An alcoholic˙HCl solution was prepared by the slow addition of acetyl chloride (0.2-3 M) to the appropriate alcohols. Treatment of the alcoholic˙HCl solution with peptides bound to 2-chlorotrityl resins gave the corresponding peptide esters (73-99% yield). Acid-sensitive protection groups, such as N-Boc, trityl tert-butyl ether, tert-butyl ester, and Pbf remained intact in the reaction.