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Issue 5, 2019
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Synthesis of endolides A and B: naturally occurring N-methylated cyclic tetrapeptides

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Abstract

Endolides A and B are naturally occurring, N-methylated, cyclic tetrapeptides possessing an unusual 3-(3-furyl)alanine amino acid and outstanding biological profiles. 1-Propanephosphonic anhydride (T3P) was used to mediate a solution-phase cyclisation reaction of the linear tetrapeptides, thus achieving the first syntheses of both endolides A and B. The stereoselectivity of the tetrapeptide cyclisation reactions was found to be reagent-controlled, and was independent of the C-terminal configuration of the linear peptide starting materials.

Graphical abstract: Synthesis of endolides A and B: naturally occurring N-methylated cyclic tetrapeptides

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Article information


Submitted
29 Jan 2019
Accepted
01 Mar 2019
First published
05 Mar 2019

Med. Chem. Commun., 2019,10, 693-698
Article type
Research Article

Synthesis of endolides A and B: naturally occurring N-methylated cyclic tetrapeptides

E. K. Davison, A. J. Cameron, P. W. R. Harris and M. A. Brimble, Med. Chem. Commun., 2019, 10, 693
DOI: 10.1039/C9MD00050J

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