48
2 Dopachrome Conversion
Fig. 2.12 Reaction scheme of dopachrome conversion
calculation results emphasize the importance of quinonoid protonation for promoting
deprotonation and decarboxylation, where electronic manipulation of π-conjugated
chains is the key to controlling the reaction.
References
1. J. Bustamante, L. Bredeston, G. Malanga, J. Mordoh, Role of melanin as a scavenger of active
oxygen species. Pigment Cell Res. 6, 348–353 (1993)
2. M. Tada, M. Kohno, Y. Niwano, Scavenging or quenching effect of melanin on superoxide
anion and singlet oxygen. J. Clin. Biochem. Nutr. 46, 224–228 (2010)
3. W. Korytowski, T. Sarna, Bleaching of melanin pigment: role of copper ions and hydrogen
peroxide in autooxidation and photooxidation of synthetic dopa-melanin. J. Biol. Chem. 265,
12410–12416 (1990)
4. L. Panzella, A. Napolitano, M. d’Ischia, Is DHICA the key to dopachrome tautomerase and
melanocyte functions? Pigment Cell Melanoma Res. 24, 248–249 (2010)
2 Dopachrome Conversion
Fig. 2.12 Reaction scheme of dopachrome conversion
calculation results emphasize the importance of quinonoid protonation for promoting
deprotonation and decarboxylation, where electronic manipulation of π-conjugated
chains is the key to controlling the reaction.
References
1. J. Bustamante, L. Bredeston, G. Malanga, J. Mordoh, Role of melanin as a scavenger of active
oxygen species. Pigment Cell Res. 6, 348–353 (1993)
2. M. Tada, M. Kohno, Y. Niwano, Scavenging or quenching effect of melanin on superoxide
anion and singlet oxygen. J. Clin. Biochem. Nutr. 46, 224–228 (2010)
3. W. Korytowski, T. Sarna, Bleaching of melanin pigment: role of copper ions and hydrogen
peroxide in autooxidation and photooxidation of synthetic dopa-melanin. J. Biol. Chem. 265,
12410–12416 (1990)
4. L. Panzella, A. Napolitano, M. d’Ischia, Is DHICA the key to dopachrome tautomerase and
melanocyte functions? Pigment Cell Melanoma Res. 24, 248–249 (2010)