References
79
13. F. García-Carmona, F. García-Cánovas, J.L. Iborra, J.A. Lozano, Kinetic study of the pathway of
melanization between L-dopa and dopachrome. Biochim. Biophys. Acta 717, 124–131 (1982)
14. S. Ito, K. Wakamatsu, Chemistry of mixed melanogenesis-pivotal roles of dopaquinone.
Photochem. Photobiol. 84, 582–592 (2008)
15. S. Ito, G. Prota, A facile one-step synthesis of cysteinyldopas using mushroom tyrosinase.
Experimentia 33, 1118–1119 (1977)
16. G. Prota, Recent advances in the chemistry of melanogenesis in mammals. J. Invest. Dermatol.
75, 122–127 (1980)
17. X. Huang, R. Xu, M.D. Hawley, T.L. Hopkins, K.J. Kramer, Electrochemical oxidation of
N-acyldopamines and regioselective reactions of their quinones with N-acetylcysteine and
thiourea. Arch. Biochem. Biophys. 352, 19–30 (1998)
18. R. Xu, X. Huang, K.J. Kramer, M.D. Hawley, Characterization of products from the reactions
of dopamine quinone with N-acetylcysteine. Bioorg. Chem. 24, 110–126 (1996)
19. G.N.L. Jameson, J. Zhang, R.F. Jameson, W. Linert, Kinetic evidence that cysteine reacts with
dopaminoquinone via reversible adduct formation to yield 5-cysteinyl-dopamine: an important
precursor of neuromelanin. Org. Biomol. Chem. 2, 777–782 (2004)
20. R. Kishida, H. Kasai, S.M. Aspera, R.L. Arevalo, H. Nakanishi, Branching reaction in melanogenesis: the effect of intramolecular cyclization on thiol binding. J. Electron. Mater. 46,
3784–3788 (2017)
21. R. Kishida, H. Kasai, S.M. Aspera, R.L. Arevalo, H. Nakanishi, Density functional theory-based
first principles calculations of rhododendrol-quinone reactions: preference to thiol binding over
cyclization. J. Phys. Soc. Jpn. 86, 024804-1–5 (2017)
22. R. Kishida, A.G. Saputro, R.L. Arevalo, H. Kasai, Effects of introduction of α-carboxylate
N-methyl and N-formyl groups on intramolecular cyclization of o-quinone amines: density
functional theory-based study. Int. J. Quant. Chem. 117, e25445-1-9 (2017)
23. P. Hohenberg, W. Kohn, Inhomogeneous electron gas. Phys. Rev. 136, B864–B871 (1964)
24. W. Kohn, L.J. Sham, Self-consistent equations including exchange and correlation effects.
Phys. Rev. 140, A1133–A1138 (1965)
25. A.D. Becke, Density-functional thermochemistry. III. The role of exact exchange. J. Chem.
Phys. 98, 5648–5652 (1993)
26. C. Lee, W. Yang, R.G. Parr, Development of the Colle-Salvetti correlation-energy formula into
a functional of the electron density. Phys. Rev. B 37, 785–789 (1988)
27. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G.
Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P.
Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota,
R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A.
Montgomery, Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin,
V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S.
Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V.
Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R.
Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth,
P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J.B. Foresman, J.V. Ortiz,
J. Cioslowski, D.J. Fox, Gaussian 09, Revision C. 01, Gaussian, Inc., Wallingford CT (2009)
28. J.P. Foster, F. Weinhold, Natural hybrid orbitals. J. Am. Chem. Soc. 102, 7211–7218 (1980)
29. J. Tomasi, B. Mennucci, R. Cammi, Quantum mechanical continuum solvation models. Chem.
Rev. 105, 2999–3093 (2005)
30. J.L. Pascual-Ahuir, E. Silla, I. Tuñon, GEPOL: an improved description of molecular surfaces.
III. A new algorithm for the computation of a solvent-excluding surface. J. Comput. Chem. 15,
1127–1138 (1994)
31. R.G. Parr, W. Yang, Density functional approatch to the frontier-electron theory of chemical
reactivity. J. Am. Chem. Soc. 106, 4049–4050 (1984)
32. P. Fuentealba, P. Pérez, R. Contreras, On the condensed Fukui function. J. Chem. Phys. 113,
2544–2551 (2000)
79
13. F. García-Carmona, F. García-Cánovas, J.L. Iborra, J.A. Lozano, Kinetic study of the pathway of
melanization between L-dopa and dopachrome. Biochim. Biophys. Acta 717, 124–131 (1982)
14. S. Ito, K. Wakamatsu, Chemistry of mixed melanogenesis-pivotal roles of dopaquinone.
Photochem. Photobiol. 84, 582–592 (2008)
15. S. Ito, G. Prota, A facile one-step synthesis of cysteinyldopas using mushroom tyrosinase.
Experimentia 33, 1118–1119 (1977)
16. G. Prota, Recent advances in the chemistry of melanogenesis in mammals. J. Invest. Dermatol.
75, 122–127 (1980)
17. X. Huang, R. Xu, M.D. Hawley, T.L. Hopkins, K.J. Kramer, Electrochemical oxidation of
N-acyldopamines and regioselective reactions of their quinones with N-acetylcysteine and
thiourea. Arch. Biochem. Biophys. 352, 19–30 (1998)
18. R. Xu, X. Huang, K.J. Kramer, M.D. Hawley, Characterization of products from the reactions
of dopamine quinone with N-acetylcysteine. Bioorg. Chem. 24, 110–126 (1996)
19. G.N.L. Jameson, J. Zhang, R.F. Jameson, W. Linert, Kinetic evidence that cysteine reacts with
dopaminoquinone via reversible adduct formation to yield 5-cysteinyl-dopamine: an important
precursor of neuromelanin. Org. Biomol. Chem. 2, 777–782 (2004)
20. R. Kishida, H. Kasai, S.M. Aspera, R.L. Arevalo, H. Nakanishi, Branching reaction in melanogenesis: the effect of intramolecular cyclization on thiol binding. J. Electron. Mater. 46,
3784–3788 (2017)
21. R. Kishida, H. Kasai, S.M. Aspera, R.L. Arevalo, H. Nakanishi, Density functional theory-based
first principles calculations of rhododendrol-quinone reactions: preference to thiol binding over
cyclization. J. Phys. Soc. Jpn. 86, 024804-1–5 (2017)
22. R. Kishida, A.G. Saputro, R.L. Arevalo, H. Kasai, Effects of introduction of α-carboxylate
N-methyl and N-formyl groups on intramolecular cyclization of o-quinone amines: density
functional theory-based study. Int. J. Quant. Chem. 117, e25445-1-9 (2017)
23. P. Hohenberg, W. Kohn, Inhomogeneous electron gas. Phys. Rev. 136, B864–B871 (1964)
24. W. Kohn, L.J. Sham, Self-consistent equations including exchange and correlation effects.
Phys. Rev. 140, A1133–A1138 (1965)
25. A.D. Becke, Density-functional thermochemistry. III. The role of exact exchange. J. Chem.
Phys. 98, 5648–5652 (1993)
26. C. Lee, W. Yang, R.G. Parr, Development of the Colle-Salvetti correlation-energy formula into
a functional of the electron density. Phys. Rev. B 37, 785–789 (1988)
27. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G.
Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P.
Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota,
R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A.
Montgomery, Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin,
V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S.
Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V.
Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R.
Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth,
P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J.B. Foresman, J.V. Ortiz,
J. Cioslowski, D.J. Fox, Gaussian 09, Revision C. 01, Gaussian, Inc., Wallingford CT (2009)
28. J.P. Foster, F. Weinhold, Natural hybrid orbitals. J. Am. Chem. Soc. 102, 7211–7218 (1980)
29. J. Tomasi, B. Mennucci, R. Cammi, Quantum mechanical continuum solvation models. Chem.
Rev. 105, 2999–3093 (2005)
30. J.L. Pascual-Ahuir, E. Silla, I. Tuñon, GEPOL: an improved description of molecular surfaces.
III. A new algorithm for the computation of a solvent-excluding surface. J. Comput. Chem. 15,
1127–1138 (1994)
31. R.G. Parr, W. Yang, Density functional approatch to the frontier-electron theory of chemical
reactivity. J. Am. Chem. Soc. 106, 4049–4050 (1984)
32. P. Fuentealba, P. Pérez, R. Contreras, On the condensed Fukui function. J. Chem. Phys. 113,
2544–2551 (2000)