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Synthesis of tetrapeptide Bz-RGDS-NH2 by a combination of chemical and enzymatic methods

Paper ID Volume ID Publish Year Pages File Format Full-Text
25629 43586 2006 8 PDF Available
Title
Synthesis of tetrapeptide Bz-RGDS-NH2 by a combination of chemical and enzymatic methods
Abstract

The tetrapeptide Bz-Arg-Gly-Asp-Ser-NH2 (Bz-RGDS-NH2) was successfully synthesized by a combination of chemical and enzymatic methods in this study. Firstly, the precursor tripeptide Gly-Asp-Ser-NH2 (GDS-NH2) was synthesized by a novel chemical method in four steps including chloroacetylation of l-aspartic acid, synthesis of chloroacetyl l-aspartic acid anhydride, the synthesis of ClCH2COAsp-SerOMe and ammonolysis of ClCH2COAsp-SerOMe. Secondly, lipase (PPL) was used to catalyze the formation of Bz-RGDS-NH2 in aqueous water-miscible organic cosolvent systems using Bz-Arg-OEt as the acyl donor and GDS-NH2 as the nucleophile. The optimum conditions were Bz-Arg-OEt 50 mM; GDS-NH2 400 mM; 10 °C, 0.1 M phosphate buffer, pH 7.5; 60% DMF or 58% DMSO, PPL: 10 mg ml−1 with the maximum yields of the tetrapeptide of 73.6% for DMF and 70.4% for DMSO, respectively. The secondary hydrolysis of the tetrapeptide product did not take place due to the absence of amidase activity of lipase.

Keywords
Bz-RGDS-NH2; Peptide synthesis; Lipase; Organic solvents
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Synthesis of tetrapeptide Bz-RGDS-NH2 by a combination of chemical and enzymatic methods
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Biotechnology - Volume 125, Issue 3, 18 September 2006, Pages 311–318
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
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Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
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Full-text PDF Download
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