Peptide Synthesis Using Carbamoylmethyl Esters as Acyl Donors Mediated by Bacillus amyloliquefaciens Protease

Title: Peptide Synthesis Using Carbamoylmethyl Esters as Acyl Donors Mediated by Bacillus amyloliquefaciens Protease

Volume: 15 Issue: 10

Author(s): Toshifumi Miyazawa, Tadamichi Shindo, Takashi Murashima and Takashi Yamada

Affiliation:

Keywords: Bacillus amyloliquefaciens protease, protease-catalyzed peptide synthesis, carbamoylmethyl ester, acyl donor, segment condensation

Abstract: Bacillus amyloliquefaciens protease-catalyzed peptide bond formation was investigated using the carbamoylmethyl (Cam) ester as the acyl donor. A series of N-protected L-amino acid Cam esters were coupled with an Lamino acid amide in acetonitrile in good to excellent yields. The superiority of the Cam ester for segment condensations was demonstrated in several 2+1 couplings. Furthermore, the couplings of racemic amino acid Cam esters as carboxyl components afforded the L-L-peptides in a highly diastereoselective manner.

Cite this article as:

Miyazawa Toshifumi, Shindo Tadamichi, Murashima Takashi and Yamada Takashi, Peptide Synthesis Using Carbamoylmethyl Esters as Acyl Donors Mediated by Bacillus amyloliquefaciens Protease, Protein & Peptide Letters 2008; 15 (10) . https://dx.doi.org/10.2174/092986608786071175