Synthesis and aromatisation of cyclic enediyne-containing amino acids

Jasper Kaiser, B. C J Van Esseveldt, M. J A Segers, Floris L. Van Delft, J. M M Smits, Sam Butterworth, F. P J T Rutjes

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)695-705
Number of pages11
JournalOrganic and Biomolecular Chemistry
Volume7
Issue number4
DOIs
Publication statusPublished - 2009

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