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

doi:10.1016/j.procbio.2008.04.020

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

Department of Chemical and Biomolecular Engineering

Research output: Contribution to journal › Article › peer-review

10 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 language	English
Pages (from-to)	999-1003
Number of pages	5
Journal	Process Biochemistry
Volume	43
Issue number	9
DOIs	https://doi.org/10.1016/j.procbio.2008.04.020
Publication status	Published - 2008 Sept

Bibliographical note

Funding Information:
This work was supported by the Korea Science and Engineering Foundation (KOSEF) grant funded by the Korea government (MOST) (No. M10755020001-07N5502-00110).

All Science Journal Classification (ASJC) codes

Bioengineering
Biochemistry
Applied Microbiology and Biotechnology

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10.1016/j.procbio.2008.04.020

Cite this

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title = "A convenient preparation of dityrosine via Mn(III)-mediated oxidation of tyrosine",

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.",

author = "Lee, {Dong Ik} and Sangpill Hwang and Choi, {Jee Yun} and Ahn, {Ik Sung} and Lee, {Chang Ha}",

note = "Funding Information: This work was supported by the Korea Science and Engineering Foundation (KOSEF) grant funded by the Korea government (MOST) (No. M10755020001-07N5502-00110).",

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AU - Lee, Dong Ik

AU - Hwang, Sangpill

AU - Choi, Jee Yun

AU - Ahn, Ik Sung

AU - Lee, Chang Ha

N1 - Funding Information: This work was supported by the Korea Science and Engineering Foundation (KOSEF) grant funded by the Korea government (MOST) (No. M10755020001-07N5502-00110).

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N2 - 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.

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

Abstract

Bibliographical note

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