Branching Reaction in Melanogenesis: The Effect of Intramolecular Cyclization on Thiol Binding

Ryo Kishida, Hideaki Kasai, Susan Meñez Aspera, Ryan Lacdao Arevalo, Hiroshi Nakanishi

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

With the aid of density functional theory-based first principles calculations, we investigated energetics and electronic structure changes in reactions involving dopaquinone to give insights into the branching behaviors in melanogenesis. The reactions we investigated are the intramolecular cyclization and thiol binding, which are competing with each other. It was found that, in order to accomplish thiol binding, charge transfer of around one electron from thiol to dopaquinone occurs. Furthermore, intramolecular cyclization of dopaquinone increases the lowest unnoccupied molecular orbital level substantially. This result clearly shows prevention of the binding of thiol by intramolecular cyclization.

Original languageEnglish
Pages (from-to)3784-3788
Number of pages5
JournalJournal of Electronic Materials
Volume46
Issue number6
DOIs
Publication statusPublished - Jun 1 2017

Fingerprint

Cyclization
Sulfhydryl Compounds
thiols
Molecular orbitals
Electronic structure
Density functional theory
Charge transfer
molecular orbitals
Electrons
charge transfer
density functional theory
electronic structure
dopaquinone
electrons

All Science Journal Classification (ASJC) codes

  • Electronic, Optical and Magnetic Materials
  • Condensed Matter Physics
  • Electrical and Electronic Engineering
  • Materials Chemistry

Cite this

Branching Reaction in Melanogenesis : The Effect of Intramolecular Cyclization on Thiol Binding. / Kishida, Ryo; Kasai, Hideaki; Aspera, Susan Meñez; Arevalo, Ryan Lacdao; Nakanishi, Hiroshi.

In: Journal of Electronic Materials, Vol. 46, No. 6, 01.06.2017, p. 3784-3788.

Research output: Contribution to journalArticle

Kishida, Ryo ; Kasai, Hideaki ; Aspera, Susan Meñez ; Arevalo, Ryan Lacdao ; Nakanishi, Hiroshi. / Branching Reaction in Melanogenesis : The Effect of Intramolecular Cyclization on Thiol Binding. In: Journal of Electronic Materials. 2017 ; Vol. 46, No. 6. pp. 3784-3788.
@article{0664dd8ce4514021ad21a6963de00f81,
title = "Branching Reaction in Melanogenesis: The Effect of Intramolecular Cyclization on Thiol Binding",
abstract = "With the aid of density functional theory-based first principles calculations, we investigated energetics and electronic structure changes in reactions involving dopaquinone to give insights into the branching behaviors in melanogenesis. The reactions we investigated are the intramolecular cyclization and thiol binding, which are competing with each other. It was found that, in order to accomplish thiol binding, charge transfer of around one electron from thiol to dopaquinone occurs. Furthermore, intramolecular cyclization of dopaquinone increases the lowest unnoccupied molecular orbital level substantially. This result clearly shows prevention of the binding of thiol by intramolecular cyclization.",
author = "Ryo Kishida and Hideaki Kasai and Aspera, {Susan Me{\~n}ez} and Arevalo, {Ryan Lacdao} and Hiroshi Nakanishi",
year = "2017",
month = "6",
day = "1",
doi = "10.1007/s11664-017-5299-x",
language = "English",
volume = "46",
pages = "3784--3788",
journal = "Journal of Electronic Materials",
issn = "0361-5235",
publisher = "Springer New York",
number = "6",

}

TY - JOUR

T1 - Branching Reaction in Melanogenesis

T2 - The Effect of Intramolecular Cyclization on Thiol Binding

AU - Kishida, Ryo

AU - Kasai, Hideaki

AU - Aspera, Susan Meñez

AU - Arevalo, Ryan Lacdao

AU - Nakanishi, Hiroshi

PY - 2017/6/1

Y1 - 2017/6/1

N2 - With the aid of density functional theory-based first principles calculations, we investigated energetics and electronic structure changes in reactions involving dopaquinone to give insights into the branching behaviors in melanogenesis. The reactions we investigated are the intramolecular cyclization and thiol binding, which are competing with each other. It was found that, in order to accomplish thiol binding, charge transfer of around one electron from thiol to dopaquinone occurs. Furthermore, intramolecular cyclization of dopaquinone increases the lowest unnoccupied molecular orbital level substantially. This result clearly shows prevention of the binding of thiol by intramolecular cyclization.

AB - With the aid of density functional theory-based first principles calculations, we investigated energetics and electronic structure changes in reactions involving dopaquinone to give insights into the branching behaviors in melanogenesis. The reactions we investigated are the intramolecular cyclization and thiol binding, which are competing with each other. It was found that, in order to accomplish thiol binding, charge transfer of around one electron from thiol to dopaquinone occurs. Furthermore, intramolecular cyclization of dopaquinone increases the lowest unnoccupied molecular orbital level substantially. This result clearly shows prevention of the binding of thiol by intramolecular cyclization.

UR - http://www.scopus.com/inward/record.url?scp=85010952784&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85010952784&partnerID=8YFLogxK

U2 - 10.1007/s11664-017-5299-x

DO - 10.1007/s11664-017-5299-x

M3 - Article

AN - SCOPUS:85010952784

VL - 46

SP - 3784

EP - 3788

JO - Journal of Electronic Materials

JF - Journal of Electronic Materials

SN - 0361-5235

IS - 6

ER -