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Difficult macrocyclizations: new strategies for synthesizing highly strained cyclic tetrapeptides.

Authors
  • Meutermans, Wim D F
  • Bourne, Gregory T
  • Golding, Simon W
  • Horton, Douglas A
  • Campitelli, Marc R
  • Craik, David
  • Scanlon, Martin
  • Smythe, Mark L
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
Jul 24, 2003
Volume
5
Issue
15
Pages
2711–2714
Identifiers
PMID: 12868896
Source
Medline
License
Unknown

Abstract

[reaction: see text] 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.

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