Stereochemical Studies on the Formation of Melanin by Monophenol Monooxygenase

Masahiro KAJIWARA; Katsuyuki KURUMAYA; Yoshiyuki KOHNO; Kenichi TOMITA; Adrian T. CARPENTER

doi:10.1248/cpb.37.3386

Masahiro KAJIWARA, Katsuyuki KURUMAYA, Yoshiyuki KOHNO, Kenichi TOMITA, Adrian T. CARPENTER

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Keywords: tyrosine, tyrosinase, dopa, melanin, dopachrome, chiral intermediate, stereoselective reaction

JOURNAL FREE ACCESS

1989 Volume 37 Issue 12 Pages 3386-3389

DOI https://doi.org/10.1248/cpb.37.3386

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Abstract

The oxidation of tyrosine by monophenol monooxygenase (tyrosinase : EC 1.10.3.1) to melanin has been studied by a combination of ultraviolet, circular dichroism, and nuclear magnetic resonance techniques. It is demonstrated that the chiral intermediate (dopachrome) is generated stereoselectively in this enzymic reaction.

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