J. So, Seunghyun Kang, Byung-Gee Kim
Aug 1, 1998
Citations
0
Influential Citations
27
Citations
Journal
Enzyme and Microbial Technology
Abstract
Abstract The lipase-catalyzed synthesis of various dipeptides containing d -amino acid was studied. Lipase from porcine pancreas (PPL) was the only lipase which catalyzed the synthesis of Bz-Tyr- d -Ala-NH 2 from Bz- l -Tyr-OEt and H- d -Ala-NH 2 . Peptide yields reached 90% in 3-methyl-3-pentanol containing 5% (v/v) buffer. To examine the S 1 and S ′ 1 site specificity of PPL, the syntheses of Bz- l -Tyr- d -aa-X and X- l -aa- d -Ala-NH 2 were performed separately. The results are summarized as follows: 1. Among various kinds of d -amino acid derivatives, H- d -Ala-NH 2 , H- d -Ser-OMe, H- d -Thr-OMe, H- d -His-OMe, and β-Ala-OMe are good acyl acceptors; 2. l -isomers of the above d -amino acids show similar reactivity for peptide synthesis, but corresponding d -isomers result in better yields; 3. In the case of histidine, only d -isomer displays S ′ 1 site substrate specificity; and 4. Besides Bz- l -Tyr-OEt, the n -protected α-carboxy ester of l -Ala, l -Arg, l -His, l -Trp, and l -Phe can be used as an acyl donor.