Difficult macrocyclizations: New strategies for synthesizing highly strained cyclic tetrapeptides

Meutermans, W., Bourne, G. T., Golding, S., Horton, D., Campitelli, M. R., Craik, D. J., Scanlon, M. J. and Smythe, M. L. (2003) Difficult macrocyclizations: New strategies for synthesizing highly strained cyclic tetrapeptides. Organic Letters, 5 15: 2711-2714. doi:10.1021/ol034907o


Author Meutermans, W.
Bourne, G. T.
Golding, S.
Horton, D.
Campitelli, M. R.
Craik, D. J.
Scanlon, M. J.
Smythe, M. L.
Title Difficult macrocyclizations: New strategies for synthesizing highly strained cyclic tetrapeptides
Journal name Organic Letters   Check publisher's open access policy
ISSN 1523-7060
Publication date 2003
Sub-type Article (original research)
DOI 10.1021/ol034907o
Volume 5
Issue 15
Start page 2711
End page 2714
Total pages 4
Editor Amos B. Smith III
Place of publication Washington, DC, USA
Publisher American Chemical Society
Collection year 2003
Language eng
Subject C1
250302 Biological and Medical Chemistry
780103 Chemical sciences
Abstract Cyclic tetrapeptides are an intriguing class of natural products. To synthesize highly strained cyclic tetrapeptides; we developed a macrocyclization strategy that involves the inclusion of 2-hydroxy-6-nitrobenzyl (HnB) group at the N-terminus and in the middle of the sequence. The N-terminal auxiliary performs a ring closure/ring contraction role, and the backbone auxiliary promotes cis amide bonds to facilitate the otherwise difficult ring contraction. Following this route, the all-L cyclic tetrapeptide cyclo-[Tyr-Arg-Phe-Ala] was successfully prepared.
Keyword Chemistry, Organic
Natural-products
Combinatorial Synthesis
Conformational-analysis
Privileged Structures
Histone Deacetylase
Nmr Spectrometry
Drug Discovery
Peptides
Chlamydocin
Cyclization
Q-Index Code C1

 
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Created: Wed, 15 Aug 2007, 02:05:39 EST