Oxidative polymerisation of 5,6-dihydroxyindole-2-carboxylic acid to melanin: A new insight

被引：56

作者：

Pezzella, A ^{[1
]}

Napolitano, A ^{[1
]}

dIschia, M ^{[1
]}

Prota, G ^{[1
]}

机构：

[1] UNIV NAPLES FEDERICO II,DEPT ORGAN & BIOL CHEM,I-80134 NAPLES,ITALY

来源：

TETRAHEDRON | 1996年 / 52卷 / 23期

关键词：

D O I：

10.1016/0040-4020(96)00362-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Previous studies on the oxidative polymerisation of 5,6-dihydroxyindole-2-carboxylic acid, a key intermediate in the biosynthesis of eumelanins, had delineated a reaction pathway involving mainly repeated coupling of the indole units through the 4- and 7- positions. Using an improved HPLC methodology for the direct analysis of oligomer intermediates, we have now obtained evidence for a more complex mode of polymerisation involving formation, besides the 4,4' and 4,7' coupled dimers 5 and 6, of three new dimers, which have been isolated and identified as the 3,4'-, 3,7'- and 7,7'-biindolyls 7-9. The observed implication of the 3-position is unprecedented in the oxidative polymerisation of 5,6-dihydroxyindoles and yields important clues for future studies aimed at elucidating the chemical constitution of natural and synthetic eumelanins. Copyright (C) 1996 Elsevier Science Ltd

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收藏

页码：7913 / 7920

页数：8

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