Design, synthesis and utilization of 1- substituted sulphonyloxy-2-phenyl benzimidazole as a novel peptide coupling reagents.
Highly efficient coupling reagents, N-methanesulphonyloxy-2-phenyl benzimidazole and N - p-toluenesulphonyloxy-2-phenyl benzimidazole were designed, synthesized and successfully applied in peptide coupling reactions. Their efficiency was evaluated by synthesizing a number of structurally different amides and peptides as well. The distereomeric purity was examined by HPLC. Also the optical rotations of all the synthesized peptides were measured and found to be quite matching with corresponding values in literature. After completion of reaction, the N-hydroxy 2-phenyl benzimidazole which was the starting material for the synthesis of reagents could be easily isolated during the work up by acid base treatment and could be re-used without significant loss in reactivity. Also the intermediate in the reaction sequence was isolated and characterized by mass and (1)H NMR which could help to comment about the probable mechanism.
Kokare
N D
ND
Department of Chemical Technology, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad-431004 (MS), India.
Nagawade
R R
RR
Rane
V P
VP
Shinde
Devanand B
DB
D001549:Benzamides / Q000138:chemical synthesis; D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D003432:Cross-Linking Reagents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015195:Drug Design; D008698:Mesylates / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D008954:Models, Biological; D014105:Tosyl Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology
D001549:Benzamides; D001562:Benzimidazoles; D003432:Cross-Linking Reagents; D008698:Mesylates; C520673:N-hydroxy-2-phenylbenzimidazole; C520621:N-methanesulfonyloxy-2-phenyl benzimidazole; C520622:N-p-toluenesulfonyloxy-2-phenyl benzimidazole; D014105:Tosyl Compounds; C037689:benzamide