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Availability of tyrosine amide for α-chymotrypsin-catalyzed synthesis of oligo-tyrosine peptides

Paper ID Volume ID Publish Year Pages File Format Full-Text
17422 42667 2009 6 PDF Available
Title
Availability of tyrosine amide for α-chymotrypsin-catalyzed synthesis of oligo-tyrosine peptides
Abstract

Oligo-tyrosine peptides such as Tyr-Tyr having angiotensin I-converting enzyme (ACE) inhibitory activity could be synthesized by α-chymotrypsin-catalyzed reaction with l-tyrosine ethyl ester in aqueous media. However, peptide yield in the reaction was below 10%. Since l-tyrosine amide showed highly nucleophilic activity for the deacylation of enzyme through which a new peptide bond was made, its application to the enzymatic peptide synthesis was evaluated in this study. Addition of tyrosine amide into the reaction produced Tyr-Tyr-NH2, of which yield exceeded 130% on the basis of tyrosine ethyl ester. Although purified Tyr-Tyr-NH2 did not inhibit ACE activity, α-chymotrypsin could act on the dipeptide amide and convert about 40% of it to Tyr-Tyr. The use of both ester and amide forms of tyrosine is expected to be a potent procedure for α-chymotrypsin-catalyzed synthesis of antihypertensive peptides.

Keywords
ACE, angiotensin I-converting enzyme; AT, N-acetyl-l-tyrosine; ATEE, N-acetyl-l-tyrosine ethyl ester; AT-Tyr-NH2, N-acetyl-l-tyrosyl-l-tyrosine amide; AT-Tyr-OEt, N-acetyl-l-tyrosyl-l-tyrosine ethyl ester; HA, hippuric acid; HHL, hippuryl histidyl leucine
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Availability of tyrosine amide for α-chymotrypsin-catalyzed synthesis of oligo-tyrosine peptides
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Publisher
Database: Elsevier - ScienceDirect
Journal: Enzyme and Microbial Technology - Volume 45, Issues 6–7, December 2009, Pages 457–462
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us