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 differences in cyclisation half-lives depending on the olefinic substituent and the ring size. A potential candidate for incorporation into peptides has been identified.
Kaiser
Jasper
J
Institute for Molecules and Materials, Radboud University Nijmegen, Heyendaalseweg 135, 6525, AJ Nijmegen, The Netherlands.
van Esseveldt
Bart C J
BC
Segers
Margot J A
MJ
van Delft
Floris L
FL
Smits
Jan M M
JM
Butterworth
Sam
S
Rutjes
Floris P J T
FP
D000480:Alkynes / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis*; D024322:Amino Acids, Aromatic / Q000138:chemical synthesis*; D003500:Cyclization; D053281:Enediynes / Q000138:chemical synthesis*; D005998:Glycine / Q000031:analogs & derivatives / Q000737:chemistry
D000480:Alkynes; D000596:Amino Acids; D024322:Amino Acids, Aromatic; D053281:Enediynes; C009055:propargylglycine; D005998:Glycine