Phenolic ester mediated oligopeptide synthesis promoted by HOBt.
Although substituted phenolic ester mediated peptide synthesis is an efficient and well established method, the same via totally unsubstituted phenyl ester is not preferred due to the extremely slow rate of aminolysis. We have investigated the scope of the unsubstituted phenyl ester as an intermediate in peptide bond formation and found that it may be useful for the design of chemoselective peptide ligation when HOBt is used as an acyl transfer catalyst. The scope of HOBt catalyzed, oxo ester mediated ligation is explored for the synthesis of oligopeptides containing a cysteine, serine and threonine at the N-terminus of the ligating peptide.
Abhijit
A
Saha
Krishna Chaitanya
KC
Nadimpally
Ashim
A
Paul
Sourav
S
Kalita
Department of Chemistry, Indian Institute of Technology Guwahati, Assam 781039, India. bmandal@iitg.ernet.in.
Bhubaneswar
B
Mandal
D000595:Amino Acid Sequence; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D004952:Esters; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D010636:Phenols / Q000737:chemistry*; D014230:Triazoles / Q000737:chemistry*
D004952:Esters; D009842:Oligopeptides; D010636:Phenols; D014230:Triazoles; C011852:1-hydroxybenzotriazole