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Panida Surawatanawong. Theoretical study of oxidative half-reaction mechanism of p-Hydroxyphenylacetate 3-Hydroxylase (HPAH). (). King Mongkut's University of Technology North Bangkok. Central Library. : , 2017.
Theoretical study of oxidative half-reaction mechanism of p-Hydroxyphenylacetate 3-Hydroxylase (HPAH)
Name: Surawit Visitsatthawong
Organization :
Mahidol University. Faculty of Science
Name: Pimchai Chaiyen
Organization :
Mahidol University. Faculty of Science
Name: Panida Surawatanawong
Organization :
Mahidol University. Faculty of Science
Email :
panida.sur@mahidol.ac.th
keyword:
Acinetobacter baumannii
LCSH:
Oxygenases
LCSH:
Hydroxylation
Abstract:
The oxygenase component (C2) of p-hydroxyphenylacetate 3-hydroxylase (HPAH)
from Acinetobacter baumannii is the flavin-dependent enzyme catalyzing the orthohydroxylation
of p-hydroxyphenylacetate (HPA) to form 3,4-dihydroxyphenylacetate (DHPA).
It was experimentally observed that C2 use reduced FMN (flavin mononucleotide) to react with
oxygen to form C4a-hydroperoxyflavin (C4aOOH) intermediate, which hydroxylates HPA to
form DHPA with 90% yield, and also eliminates H2O2 with 0.5-2% yield. In this work, we use
density functional theory to investigate both pathways. B3LYP/6-31G(d) was used to perform
gas-phase geometry optimizations, then B3LYP/6-311+G(d,p) was used to calculate solvent
corrections with the conductor-like polarizable continuum model, UAKS radii and the dielectric
constant of 4.0. We found that C2 catalyzes hydroxylation via electrophilic aromatic
substitution mechanism. His120 abstracts the phenolic proton from HPA to increase its
nucleophilicity while the heterolytic O-O bond cleavage of C4aOOH generates OH
electrophile, which attacks the C3-position of HPA. The energy barrier of hydroxylation is 22.8
kcal/mol. For the side reaction, OOH moiety dissociates from C4a of isoalloxazine ring to
abstract the proton at N5 to generate H2O2. The energy barrier of H2O2 elimination is 11.9
kcal/mol. Although the result is still inconsistent with the experiments because the energy
barrier of hydroxylation is higher than that of H2O2 elimination. This work indicates that the
active site residues incorporated in this model is insufficient to explain these reactions. More
active site residues will be included together with the use of quantum mechanical/molecular
mechanical (QM/MM) method in the future study.
King Mongkut's University of Technology North Bangkok. Central Library
Address:
BANGKOK
Email:
library@kmutnb.ac.th
Created:
2017
Modified:
2562-08-26
Issued:
2019-08-26
บทความ/Article
application/pdf
BibliograpyCitation :
In Chemical Society of Thailand under the Patronage of Her Royal Hghness Princess Chulabhorn Mahidol and King Mongkut's University of Technology North Bangkok Faculty of Applied Science. Pure and Applied Chemistry International Conference (PACCON 2017) (pp.1406-1411). Bangkok : Chemical Society of Thailand under the Patronage of Her Royal Hghness Princess Chulabhorn Mahidol
eng
©copyrights King Mongkut's University of Technology North Bangkok
RightsAccess:
ใช้เวลา
0.033407 วินาที
Surawit Visitsatthawong
| Title | Contributor | Type |
|---|---|---|
| Theoretical study of oxidative half-reaction mechanism of p-Hydroxyphenylacetate 3-Hydroxylase (HPAH)
มหาวิทยาลัยเทคโนโลยีพระจอมเกล้าพระนครเหนือ Surawit Visitsatthawong;Pimchai Chaiyen;Panida Surawatanawong | บทความ/Article |
Pimchai Chaiyen
| Title | Contributor | Type |
|---|---|---|
| Theoretical study of oxidative half-reaction mechanism of p-Hydroxyphenylacetate 3-Hydroxylase (HPAH)
มหาวิทยาลัยเทคโนโลยีพระจอมเกล้าพระนครเหนือ Surawit Visitsatthawong;Pimchai Chaiyen;Panida Surawatanawong | บทความ/Article | |
| Overexpression of pyranose dehydrogenase in E.coli platform
มหาวิทยาลัยเทคโนโลยีพระจอมเกล้าพระนครเหนือ Pangrum Punthong;Litavadee Chuaboon;Jeerus Sucharitakul;Pimchai Chaiyen;Thanyaporn Wongnate | บทความ/Article | |
| Expression and characterization of novel aldehyde deformylating oxygenase from Pseudomonas plecoglossicida
มหาวิทยาลัยเทคโนโลยีพระจอมเกล้าพระนครเหนือ Supacha Buttranon;Juthamas Jaroensuk;Jeerus Sucharitakul;Pimchai Chaiyen;Thanyaporn Wongnate | บทความ/Article | |
| Characterization of 2-oxo-hept-3-ene-1,7-dioic acid hydratase from Acinetobacter baumannii
มหาวิทยาลัยเทคโนโลยีพระจอมเกล้าพระนครเหนือ Wachirawit Chinantuya;Pirom Chenprakon;Ruchanok Tinikul;Pimchai Chaiyen | บทความ/Article |
Panida Surawatanawong