Synthesis and aromatisation of cyclic enediyne-containing amino acids

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 differ...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2009-01, Vol.7 (4), p.695-705
Main 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
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Amino Acids - chemical synthesis
Amino Acids, Aromatic - chemical synthesis
Cyclization
Enediynes - chemical synthesis
Glycine - analogs & derivatives
Glycine - chemistry
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/b815176h