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Large-scale production of N,N′-diBoc-dityrosine and dityrosine by HRP-catalyzed N-Boc-l-tyrosine oxidation and one-step chromatographic purification

Paper ID Volume ID Publish Year Pages File Format Full-Text
35367 45088 2011 6 PDF Available
Title
Large-scale production of N,N′-diBoc-dityrosine and dityrosine by HRP-catalyzed N-Boc-l-tyrosine oxidation and one-step chromatographic purification
Abstract

Dityrosine (DY) can be used as a biomarker to detect oxidative protein damage and selective proteolysis. It is generally prepared by horseradish peroxidase (HRP)-catalyzed oxidation of l-tyrosine (Y) followed by multistep chromatographic separations. In this study, we present an alternative method for the preparation of DY by HRP-catalyzed synthesis of N,N′-diBoc-dityrosine (DBDY) from N-Boc-l-tyrosine (BY). The presence of the tert-butoxycarbonyl (Boc) group ensured that the fraction of further oxidized by-products (e.g., trimers and pulcherosine) was quite low. The yield of DBDY (37.5%) was comparable to that reported for DY (> 26%). DBDY could be purified by a simple one-step silica column chromatography procedure that resulted in a purity of 89.7%. DBDY is considered to be better than DY for subsequent chemical reactions (for binding to polymers, amino acids, drugs, antibodies, etc.) because such reactions can be selectively performed by using the carboxylic acid and amine groups in the following sequence: first, the carboxylic acid groups are used; next, the Boc groups are removed; and finally, the amino groups are used. To prepare DY, the Boc groups in DBDY were simply and completely removed by treatment with trifluoroacetic acid.

Keywords
N,N′-diBoc-dityrosine; Dityrosine; Horseradish peroxidase; Large-scale production; Chromatography
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Large-scale production of N,N′-diBoc-dityrosine and dityrosine by HRP-catalyzed N-Boc-l-tyrosine oxidation and one-step chromatographic purification
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Publisher
Database: Elsevier - ScienceDirect
Journal: Process Biochemistry - Volume 46, Issue 1, January 2011, Pages 142–147
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