b-Alanyl peptide synthesis by Streptomyces S9 aminopeptidase
Synthesis of b-alanine (b-Ala) containing dipeptide using S9 aminopeptidase from Streptomyces thermocyaneoviolaceus NBRC14271 (S9AP-St) was demonstrated with b-Ala-benzyl ester (-OBzl) and various l-aminoacyl derivatives. For synthesis of b-Ala-containing dipeptide, b-Ala-OBzl was used preferentiall...
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Published in | Journal of biotechnology Vol. 147; no. 1; pp. 52 - 58 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
03.05.2010
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Abstract | Synthesis of b-alanine (b-Ala) containing dipeptide using S9 aminopeptidase from Streptomyces thermocyaneoviolaceus NBRC14271 (S9AP-St) was demonstrated with b-Ala-benzyl ester (-OBzl) and various l-aminoacyl derivatives. For synthesis of b-Ala-containing dipeptide, b-Ala-OBzl was used preferentially as the acyl donor for S9AP-St, producing synthesized dipeptides having b-Ala-Xaa structure. In contrast, engineering of S9AP-St into "transaminopeptidase" by substitution of catalytic Ser with Cys - designated as aminolysin-S - produced only dipeptides having Xaa-b-Ala structure. Investigation of the specificity of S9AP-St toward acyl acceptors showed that S9AP has a broad substrate specificity toward various aminoacyl derivatives. Furthermore, S9AP-St produced carnosine methyl ester (-OMe) with a conversion ratio of b-Ala-OBzl to carnosine-OMe that was greater than 30%. |
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AbstractList | Synthesis of b-alanine (b-Ala) containing dipeptide using S9 aminopeptidase from Streptomyces thermocyaneoviolaceus NBRC14271 (S9AP-St) was demonstrated with b-Ala-benzyl ester (-OBzl) and various l-aminoacyl derivatives. For synthesis of b-Ala-containing dipeptide, b-Ala-OBzl was used preferentially as the acyl donor for S9AP-St, producing synthesized dipeptides having b-Ala-Xaa structure. In contrast, engineering of S9AP-St into "transaminopeptidase" by substitution of catalytic Ser with Cys - designated as aminolysin-S - produced only dipeptides having Xaa-b-Ala structure. Investigation of the specificity of S9AP-St toward acyl acceptors showed that S9AP has a broad substrate specificity toward various aminoacyl derivatives. Furthermore, S9AP-St produced carnosine methyl ester (-OMe) with a conversion ratio of b-Ala-OBzl to carnosine-OMe that was greater than 30%. |
Author | Mori, Nobuhiro Usuki, Hirokazu Arima, Jiro Hatanaka, Tadashi Morimoto, Masazumi |
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Title | b-Alanyl peptide synthesis by Streptomyces S9 aminopeptidase |
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