CHARACTERIZATION OF 1,4-BENZOTHIAZINE INTERMEDIATES IN THE OXIDATIVE CONVERSION OF 5-S-CYSTEINYLDOPA TO PHEOMELANINS

被引:25
作者
NAPOLITANO, A [1 ]
COSTANTINI, C [1 ]
CRESCENZI, O [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/S0040-4039(00)73434-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Under biologically relevant conditions, oxidation of 5-S-cysteinyldopa (1) to pheomelanins proceeds through the formation of the 1,4-benothiazine 7 along with the 3-carboxy analogue 6 in much smaller amounts, as evidenced by isolation of the reduced forms 5 and 4 and by deuterium labelling experiments.
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页码:6365 / 6368
页数:4
相关论文
共 11 条
[1]   1,4-BENZOTHIAZINES, DIHYDRO-1,4-BENZOTHIAZINES, AND RELATED-COMPOUNDS [J].
BROWN, C ;
DAVIDSON, RM .
ADVANCES IN HETEROCYCLIC CHEMISTRY, 1985, 38 :135-176
[2]   NEW INTERMEDIATES OF PHAEOMELANOGENESIS INVITRO BEYOND THE 1,4-BENZOTHIAZINE STAGE [J].
COSTANTINI, C ;
CRESCENZI, O ;
PROTA, G ;
PALUMBO, A .
TETRAHEDRON, 1990, 46 (19) :6831-6838
[3]   NON-ENZYMIC OXIDATION OF CYSTEINYLDOPA CATALYZED BY METALLIC-IONS [J].
PALUMBO, A ;
NARDI, G ;
DISCHIA, M ;
MISURACA, G ;
PROTA, G .
GENERAL PHARMACOLOGY, 1983, 14 (02) :253-257
[5]   RECENT ADVANCES IN THE CHEMISTRY OF MELANOGENESIS IN MAMMALS [J].
PROTA, G .
JOURNAL OF INVESTIGATIVE DERMATOLOGY, 1980, 75 (01) :122-127
[6]   SYNTHESIS AND PHOTOCHROMISM OF DELTA 2,2'-BI-(2H-1,4-BENZOTHIAZINE) [J].
PROTA, G ;
PONSIGLI.E ;
RUGGIERO, R .
TETRAHEDRON, 1974, 30 (16) :2781-2784
[7]  
PROTA G, 1970, EXPERIENTIA, V26, P1508
[8]  
Prota G., 1992, MELANINS MELANOGENES
[9]  
PROTA G, 1969, GAZZ CHIM ITAL, V90, P1193
[10]   PHEOMELANIN AS WELL AS EUMELANIN IS PRESENT IN HUMAN EPIDERMIS [J].
THODY, AJ ;
HIGGINS, EM ;
WAKAMATSU, K ;
ITO, S ;
BURCHILL, SA ;
MARKS, JM .
JOURNAL OF INVESTIGATIVE DERMATOLOGY, 1991, 97 (02) :340-344