Synthesis and
aromatisation of cyclic enediyne-containing amino acids
Kaiser J , van Esseveldt BCJ , Segers MJA , van Delft FL, Smits JMM ,
Butterworth S , Rutjes FPJT
ORGANIC & BIOMOLECULAR CHEMISTRY Volume:
7 Issue: 4 Pages: 695-705
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.