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Design, Synthesis and Utilization of 1- Substituted Sulphonyloxy-2-Phenyl Benzimidazole as a Novel Peptide Coupling Reagents

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Highly efficient coupling reagents, N-methanesulphonyloxy-2-phenyl benzimidazole and N - ptoluenesulphonyloxy- 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 1H NMR which could help to comment about the probable mechanism.

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Keywords: Amide synthesis; HOBt; Mesyl chloride; Minimum racemization; N-Hydroxy-2-phenyl benzimidazole; Peptide-coupling reagents

Document Type: Research Article

Affiliations: Department of Chemical Technology, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad-431004 (MS), India.

Publication date: 2007-03-01

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  • Protein & Peptide Letters publishes short papers in all important aspects of protein and peptide research, including structural studies, recombinant expression, function, synthesis, enzymology, immunology, molecular modeling, drug design etc. Manuscripts must have a significant element of novelty, timeliness and urgency that merit rapid publication. Reports of crystallisation, and preliminary structure determinations of biologically important proteins are acceptable. Purely theoretical papers are also acceptable provided they provide new insight into the principles of protein/peptide structure and function.
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