Chemical analysis of late stages of pheomelanogenesis: conversion of dihydrobenzothiazine to a benzothiazole structure

K Wakamatsu, K Ohtara, S Ito - Pigment Cell & Melanoma …, 2009 - Wiley Online Library
Pheomelanogenesis is a complex pathway that starts with the oxidation of tyrosine (or
DOPA, 3, 4‐dihydroxyphenylalanine) by tyrosinase in the presence of cysteine, which …

Acid hydrolysis reveals a low but constant level of pheomelanin in human black to brown hair

S Ito, S Miyake, S Maruyama, I Suzuki… - Pigment cell & …, 2018 - Wiley Online Library
We previously reported a constant ratio of the benzothiazole pheomelanin marker thiazole‐
2, 4, 5‐tricarboxylic acid (TTCA) to the eumelanin marker pyrrole‐2, 3, 5‐tricarboxylic acid …

The “Benzothiazine” Chromophore of Pheomelanins: A Reassessment

A Napolitano, M De Lucia, L Panzella… - Photochemistry and …, 2008 - Wiley Online Library
The characteristic absorption and photochemical properties of pheomelanins are generally
attributed to “benzothiazine” structural units derived biogenetically from 5‐S‐cysteinyldopa …

1, 4‐Benzothiazines as key intermediates in the biosynthesis of red hair pigment pheomelanins

PD Donato, A Napolitano - Pigment Cell Research, 2003 - Wiley Online Library
Following the discovery of cysteinyldopas as the early intermediates in the biogenesis of
pheomelanins, the typical red hair pigments, the reactivity of the biosynthetic precursors …

Isomeric cysteinyldopas provide a (photo) degradable bulk component and a robust structural element in red human hair pheomelanin

G Greco, K Wakamatsu, L Panzella, S Ito… - Pigment cell & …, 2009 - Wiley Online Library
Alkaline H2O2 degradation of red hair pheomelanin gave, besides 6‐(2‐amino‐2‐
carboxyethyl)‐2‐carboxy‐4‐hydroxybenzothiazole (BTCA), a new product which was …

Transient quinonimines and 1, 4-benzothiazines of pheomelanogenesis: new pulse radiolytic and spectrophotometric evidence

A Napolitano, P Di Donato, G Prota, EJ Land - Free Radical Biology and …, 1999 - Elsevier
Biosynthetic and model in vitro studies have shown that pheomelanins, the distinctive
pigments of red human hair, arise by oxidative cyclization of cysteinyldopas mainly 5-S …

A new insight in the biosynthesis of pheomelanins: characterization of a labile 1, 4-benzothiazine intermediate

A Napolitano, S Memoli, G Prota - The Journal of organic …, 1999 - ACS Publications
It has long been known that pheomelanins, the distinctive pigments of red hair and celtic
skin, arise by the oxidative cyclization of cysteinyldopas, mainly the 5-S-isomer 1, via 1, 4 …

Chemical characterization of pheomelanogenesis starting from dihydroxyphenylalanine or tyrosine and cysteine.: Effects of tyrosinase and cysteine concentrations …

H Ozeki, S Ito, K Wakamatsu, I Ishiguro - Biochimica et Biophysica Acta …, 1997 - Elsevier
Two types of melanin pigment are produced in mammals; the brown-to-black eumelanins
and the yellow-to-reddish-brown pheomelanins. The switch from one type of melanin to the …

Pheomelanogenesis is promoted at a weakly acidic pH

K Wakamatsu, A Nagao, M Watanabe… - Pigment cell & …, 2017 - Wiley Online Library
The diversity of pigmentation in the skin, hair, and eyes of humans has been largely
attributed to the diversity of pH in melanosomes with an acidic pH being proposed to …

New regulatory mechanisms in the biosynthesis of pheomelanins: rearrangement vs. redox exchange reaction routes of a transient 2H-1, 4-benzothiazine-o …

A Napolitano, P Di Donato, G Prota - Biochimica et Biophysica Acta (BBA) …, 2000 - Elsevier
Pheomelanins, the typical epidermal pigments of red haired, Celtic-type Caucasians, arise
from oxidative cyclization of cysteinyldopas, mainly the 5-S-isomer CD, via 1, 4 …