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Synthesis and aromatisation of cyclic enediyne-containing amino acids.

Authors
  • Kaiser, Jasper
  • van Esseveldt, Bart C J
  • Segers, Margot J A
  • van Delft, Floris L
  • Smits, Jan M M
  • Butterworth, Sam
  • Rutjes, Floris P J T
Type
Published Article
Journal
Organic & Biomolecular Chemistry
Publisher
The Royal Society of Chemistry
Publication Date
Feb 21, 2009
Volume
7
Issue
4
Pages
695–705
Identifiers
DOI: 10.1039/b815176h
PMID: 19194585
Source
Medline
License
Unknown

Abstract

A series of cyclic enediyne-containing amino acids with ring sizes varying from 10 to 12 atoms have been prepared starting from propargylglycine and homopropargylglycine. Their reactivity towards Bergman cyclisation under elevated temperatures has been explored. The enediynes displayed marked differences in cyclisation half-lives depending on the olefinic substituent and the ring size. A potential candidate for incorporation into peptides has been identified.

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