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Preparation of thioesters for the ligation of peptides with non-native substrates

Mapp, Anna K. and Dervan, Peter B. (2000) Preparation of thioesters for the ligation of peptides with non-native substrates. Tetrahedron Letters, 41 (49). pp. 9451-9454. ISSN 0040-4039. http://resolver.caltech.edu/CaltechAUTHORS:20160510-083052068

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Abstract

A one-pot procedure for the synthesis of thioesters from primary amines is reported. Polyamides containing one or more primary amines were prepared by solid-phase synthesis and reacted with thiolane-2,5-dione followed by alkylation with benzyl bromide to produce the target thioesters in good yield. The thioesters thus prepared were conjugated to peptides to produce polyamide–peptide chimeras using the ‘native chemical ligation’ method. This flexible synthetic procedure provides a ready route to both natural and unnatural substrates for chemical ligation reactions.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1016/S0040-4039(00)01600-2DOIArticle
http://www.sciencedirect.com/science/article/pii/S0040403900016002PublisherArticle
Additional Information:© 2000 Elsevier Science Ltd. Received 31 August 2000; revised 12 September 2000; accepted 14 September 2000. We are grateful to the National Institutes of Health for support of this work (GM-27681) and a National Research Service Award to A.K.M.
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Funding AgencyGrant Number
NIHGM-27681
NIH Predoctoral FellowshipUNSPECIFIED
Record Number:CaltechAUTHORS:20160510-083052068
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20160510-083052068
Official Citation:Anna K Mapp, Peter B Dervan, Preparation of thioesters for the ligation of peptides with non-native substrates, Tetrahedron Letters, Volume 41, Issue 49, 2 December 2000, Pages 9451-9454, ISSN 0040-4039, http://dx.doi.org/10.1016/S0040-4039(00)01600-2. (http://www.sciencedirect.com/science/article/pii/S0040403900016002)
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:66830
Collection:CaltechAUTHORS
Deposited By: Victoria Brennan
Deposited On:10 May 2016 19:39
Last Modified:10 May 2016 19:39

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