Click chemistry aided synthesis of 1,4-substituted 1,2,3-triazole based N-Fmoc protected epsilon-amino acids: isolation, characterization and synthesis of novel triazole based unnatural amino acids.
A new class of 1,4-substituted 1,2,3-triazole-based unnatural amino acids is demonstrated by employing click reaction between N-Fmoc amino alkyl azides and propiolic acid. The resulting unnatural amino acids were isolated and then subjected to Fmoc deprotection to isolate 1,2,3-triazole based amino acids as stable solids. These new class of molecules were also used for chain extension from both N- and C-terminals to synthesize dipeptidomimetics bearing 1,2,3-triazole moiety in the backbone.
Sureshbabu
Vommina V
VV
Peptide Research Laboratory, Department of Studies in Chemistry, Central College Campus, Bangalore University, Dr. B. R. Ambedkar Veedhi, Bangalore -560 001, India. hariccb@hotmail.com
Narendra
N
N
Hemantha
H P
HP
Chennakrishnareddy
G
G
D000596:Amino Acids / Q000737:chemistry*; D055598:Chemical Phenomena; D004151:Dipeptides / Q000737:chemistry; D005449:Fluorenes / Q000737:chemistry*; D008968:Molecular Conformation; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry*
D000596:Amino Acids; D004151:Dipeptides; D005449:Fluorenes; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D014230:Triazoles