A convenient preparation of dityrosine via Mn(III)-mediated oxidation of tyrosine

Dong Ik Lee, Sangpill Hwang, Jee Yun Choi, Ik Sung Ahn, Chang Ha Lee

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

A simple method to rapidly and conveniently prepare dityrosine from l-tyrosine was developed using Mn(III) as an oxidizing agent. The best yield of the reaction was obtained from the 1 min equimolar reaction of l-tyrosine with Mn(III) acetate in 0.2 M sodium phosphate solution (pH 2.1) at 25 °C. Phosphate was removed by precipitation in ammonia water. The remaining tyrosine was mostly eliminated by precipitation in cold acidic water. Dityrosine was then further purified by HPLC, and its chemical structure was identified by NMR spectroscopy. Even though the yield was only 15.8%, this one-step Mn(III)-mediated oxidation of tyrosine allows dityrosine to be prepared without the need for complicated multi-step organic reactions.

Original languageEnglish
Pages (from-to)999-1003
Number of pages5
JournalProcess Biochemistry
Volume43
Issue number9
DOIs
Publication statusPublished - 2008 Sep 1

Fingerprint

Tyrosine
Phosphates
Oxidation
Nuclear magnetic resonance spectroscopy
Water
Ammonia
Sodium
Oxidants
Acetates
Magnetic Resonance Spectroscopy
High Pressure Liquid Chromatography
dityrosine

All Science Journal Classification (ASJC) codes

  • Bioengineering
  • Biochemistry
  • Applied Microbiology and Biotechnology

Cite this

Lee, Dong Ik ; Hwang, Sangpill ; Choi, Jee Yun ; Ahn, Ik Sung ; Lee, Chang Ha. / A convenient preparation of dityrosine via Mn(III)-mediated oxidation of tyrosine. In: Process Biochemistry. 2008 ; Vol. 43, No. 9. pp. 999-1003.
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A convenient preparation of dityrosine via Mn(III)-mediated oxidation of tyrosine. / Lee, Dong Ik; Hwang, Sangpill; Choi, Jee Yun; Ahn, Ik Sung; Lee, Chang Ha.

In: Process Biochemistry, Vol. 43, No. 9, 01.09.2008, p. 999-1003.

Research output: Contribution to journalArticle

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AB - A simple method to rapidly and conveniently prepare dityrosine from l-tyrosine was developed using Mn(III) as an oxidizing agent. The best yield of the reaction was obtained from the 1 min equimolar reaction of l-tyrosine with Mn(III) acetate in 0.2 M sodium phosphate solution (pH 2.1) at 25 °C. Phosphate was removed by precipitation in ammonia water. The remaining tyrosine was mostly eliminated by precipitation in cold acidic water. Dityrosine was then further purified by HPLC, and its chemical structure was identified by NMR spectroscopy. Even though the yield was only 15.8%, this one-step Mn(III)-mediated oxidation of tyrosine allows dityrosine to be prepared without the need for complicated multi-step organic reactions.

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