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
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
引用
收藏
页码:7913 / 7920
页数:8
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