Hajime Hirao

Summary

Affiliation: Nanyang Technological University
Country: Singapore

Publications

  1. pmc Importance of H-abstraction in the final step of nitrosoalkane formation in the mechanism-based inactivation of cytochrome P450 by amine-containing drugs
    Hajime Hirao
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link 637371, Singapore
    Int J Mol Sci 14:24692-705. 2013
  2. doi request reprint Guanine binding to gold nanoparticles through nonbonding interactions
    Xi Zhang
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore637371
    Phys Chem Chem Phys 15:19284-92. 2013
  3. doi request reprint How is a metabolic intermediate formed in the mechanism-based inactivation of cytochrome P450 by using 1,1-dimethylhydrazine: hydrogen abstraction or nitrogen oxidation?
    Hajime Hirao
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371
    Chemistry 19:7361-9. 2013
  4. doi request reprint Pivotal role of water in terminating enzymatic function: a density functional theory study of the mechanism-based inactivation of cytochromes P450
    Hajime Hirao
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore
    J Phys Chem B 116:7787-94. 2012
  5. pmc Theoretical study of the mechanism of oxoiron(IV) formation from H2O2 and a nonheme iron(II) complex: O-O cleavage involving proton-coupled electron transfer
    Hajime Hirao
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371
    Inorg Chem 50:6637-48. 2011
  6. doi request reprint The effects of protein environment and dispersion on the formation of ferric-superoxide species in myo-inositol oxygenase (MIOX): a combined ONIOM(DFT:MM) and energy decomposition analysis
    Hajime Hirao
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371
    J Phys Chem B 115:11278-85. 2011
  7. doi request reprint ONIOM(DFT:MM) study of 2-hydroxyethylphosphonate dioxygenase: what determines the destinies of different substrates?
    Hajime Hirao
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371, Singapore
    J Am Chem Soc 133:14550-3. 2011
  8. doi request reprint Which DFT functional performs well in the calculation of methylcobalamin? Comparison of the B3LYP and BP86 functionals and evaluation of the impact of empirical dispersion correction
    Hajime Hirao
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371
    J Phys Chem A 115:9308-13. 2011
  9. doi request reprint 1-(2'-Anilinyl)prop-2-yn-1-ol rearrangement for oxindole synthesis
    Prasath Kothandaraman
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore
    Chemistry 19:1978-85. 2013
  10. doi request reprint A general palladium-catalyzed method for alkylation of heteroarenes using secondary and tertiary alkyl halides
    Xiaojin Wu
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, 637371 Singapore
    Angew Chem Int Ed Engl 53:13573-7. 2014

Collaborators

  • Yongxin Li
  • Keiji Morokuma
  • Jean Cyrille Hierso
  • Dan Li
  • Xi Zhang
  • Chang Q Sun
  • Lawrence Que
  • Jianrong Steve Zhou
  • Xiaojin Wu
  • Che Chang Chong
  • Rei Kinjo
  • Jingjing Cui
  • Nandun M Thellamurege
  • Xiaoqing Wang
  • Zhiyan Huang
  • Nandun Thellamurege
  • Weidong Rao
  • Jian Hu
  • Prasath Kothandaraman
  • Hui Xian Yeong
  • Liena Qin
  • Philip Wai Hong Chan
  • Rakesh Ganguly
  • Jessica Wei Ting See
  • Anusiya Inthirarajah
  • Kai Xu
  • Julien Roger
  • Bozhen Chen
  • Cheuk Wai So
  • Li Hui Lim
  • Zuliang Chen
  • Yunpeng Lu
  • Bing Qin Koh
  • Kai Chung Lau
  • Sophy Bhasi Kunnappilly
  • Gia Chuong Phan Quang
  • Hong Wei Xi
  • Kok Hwa Lim
  • Taweetham Limpanuparb
  • Ming Joo Koh

Detail Information

Publications21

  1. pmc Importance of H-abstraction in the final step of nitrosoalkane formation in the mechanism-based inactivation of cytochrome P450 by amine-containing drugs
    Hajime Hirao
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link 637371, Singapore
    Int J Mol Sci 14:24692-705. 2013
    ..Our theoretical analysis of the interaction between the MI and pentacoordinate heme moieties provided further insights into the coordination bond in the MIC. ..
  2. doi request reprint Guanine binding to gold nanoparticles through nonbonding interactions
    Xi Zhang
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore637371
    Phys Chem Chem Phys 15:19284-92. 2013
    ....
  3. doi request reprint How is a metabolic intermediate formed in the mechanism-based inactivation of cytochrome P450 by using 1,1-dimethylhydrazine: hydrogen abstraction or nitrogen oxidation?
    Hajime Hirao
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371
    Chemistry 19:7361-9. 2013
    ..The aminonitrene-type MI binds to the ferric heme more strongly than a water molecule. This is consistent with the notion that the catalytic cycle of P450 is impeded when such an MI is produced through the P450-catalyzed reaction...
  4. doi request reprint Pivotal role of water in terminating enzymatic function: a density functional theory study of the mechanism-based inactivation of cytochromes P450
    Hajime Hirao
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore
    J Phys Chem B 116:7787-94. 2012
    ..Another type of MBI by acetylenes, N-alkylation of the heme prosthetic group, was less favorable than the threonine modification pathway...
  5. pmc Theoretical study of the mechanism of oxoiron(IV) formation from H2O2 and a nonheme iron(II) complex: O-O cleavage involving proton-coupled electron transfer
    Hajime Hirao
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371
    Inorg Chem 50:6637-48. 2011
    ....
  6. doi request reprint The effects of protein environment and dispersion on the formation of ferric-superoxide species in myo-inositol oxygenase (MIOX): a combined ONIOM(DFT:MM) and energy decomposition analysis
    Hajime Hirao
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371
    J Phys Chem B 115:11278-85. 2011
    ..The dispersion effect enhances O(2) binding more significantly than these effects. Despite these stabilizing effects, the entropy effect disfavors O(2) binding, making the process almost thermoneutral...
  7. doi request reprint ONIOM(DFT:MM) study of 2-hydroxyethylphosphonate dioxygenase: what determines the destinies of different substrates?
    Hajime Hirao
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371, Singapore
    J Am Chem Soc 133:14550-3. 2011
    ..Thus, the PCET plays a critical role in defining the fates of the substrates...
  8. doi request reprint Which DFT functional performs well in the calculation of methylcobalamin? Comparison of the B3LYP and BP86 functionals and evaluation of the impact of empirical dispersion correction
    Hajime Hirao
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371
    J Phys Chem A 115:9308-13. 2011
    ..B3P86-D also performed well. A detailed analysis was undertaken to determine which atoms in cobalamin have large dispersion interactions with a methyl fragment of MeCbl...
  9. doi request reprint 1-(2'-Anilinyl)prop-2-yn-1-ol rearrangement for oxindole synthesis
    Prasath Kothandaraman
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore
    Chemistry 19:1978-85. 2013
    ..Density functional theory (DFT) calculations based on proposed iodoaminocyclization species provide insight into this unique divergence in product selectivity...
  10. doi request reprint A general palladium-catalyzed method for alkylation of heteroarenes using secondary and tertiary alkyl halides
    Xiaojin Wu
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, 637371 Singapore
    Angew Chem Int Ed Engl 53:13573-7. 2014
    ..Most classes of heterocycles, including indoles and pyridines, efficiently coupled with unactivated secondary and tertiary alkyl halides. An alkyl radical addition to neutral heteroarenes is most likely involved. ..
  11. doi request reprint Water complexes of cytochrome P450: insights from energy decomposition analysis
    Nandun Thellamurege
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences Nanyang Technological University, 21 Nanyang Link, Singapore 637371, Singapore
    Molecules 18:6782-91. 2013
    ..The hydrogen bonding in the Cpd I•••H₂O complex is similar to that in the water dimer; however, the relative importance of the electrostatic effect is somewhat larger in the water dimer...
  12. doi request reprint ONIOM (DFT:MM) study of the catalytic mechanism of myo-inositol monophosphatase: essential role of water in enzyme catalysis in the two-metal mechanism
    Xiaoqing Wang
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371
    J Phys Chem B 117:833-42. 2013
    ..Our results should advance our understanding of the IMPase mechanism, and this could have profound implications for the treatment of disease in the central nervous system...
  13. doi request reprint Metal-free σ-bond metathesis in 1,3,2-diazaphospholene-catalyzed hydroboration of carbonyl compounds
    Che Chang Chong
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Nanyang Link 21, Singapore 637371 Singapore
    Angew Chem Int Ed Engl 54:190-4. 2015
    ..Thus, the reaction proceeds through a non-metal σ-bond metathesis. Kinetic and computational studies suggest that the σ-bond metathesis occurred in a stepwise but nearly concerted manner. ..
  14. doi request reprint Metal-free σ-bond metathesis in ammonia activation by a diazadiphosphapentalene
    Jingjing Cui
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, and NTU CBC Crystallography Facility, Nanyang Technological University, Singapore 637371, Singapore
    J Am Chem Soc 136:16764-7. 2014
    ..Details of the reaction mechanism for ammonia activation as well as subsequent isomerization were explored by density functional theory calculations. ..
  15. doi request reprint Effect of protein environment within cytochrome P450cam evaluated using a polarizable-embedding QM/MM method
    Nandun M Thellamurege
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371
    J Phys Chem B 118:2084-92. 2014
    ....
  16. doi request reprint Zwitterionic base-stabilized digermadistannacyclobutadiene and tetragermacyclobutadiene
    Hui Xian Yeong
    Division of Chemistry and Biological Chemistry, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 Singapore, Fax 65 6791 1961
    Chemistry 19:14726-31. 2013
    ..X-ray structural data and theoretical studies show conclusively that compounds 3 and 9 have a planar and rhombic charge-separated structure. They are also nonaromatic. ..
  17. doi request reprint Regioselective Heck reaction of aliphatic olefins and aryl halides
    Liena Qin
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371
    Chem Commun (Camb) 49:10236-8. 2013
    ..Methanol solvent promoted halide ionization from neutral arylpalladium halide complexes via hydrogen bonding, so as to create cationic aryl-Pd species for regioselective olefin insertion. ..
  18. doi request reprint Palladium-catalyzed asymmetric intermolecular cyclization
    Jian Hu
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 Singapore
    Angew Chem Int Ed Engl 52:8676-80. 2013
    ..The method was applied to the asymmetric synthesis of a precursor of (-)-martinellic acid, a folk eye medicine in South America. ..
  19. doi request reprint Weak arene ch⋅⋅⋅o hydrogen bonding in palladium-catalyzed arylation and vinylation of lactones
    Zhiyan Huang
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 Singapore
    Angew Chem Int Ed Engl 52:5807-12. 2013
    ..A similar palladium catalyst (right) used conventional NH⋅⋅⋅O hydrogen bonding to guide stereoselection...
  20. doi request reprint Achieving vinylic selectivity in Mizoroki-Heck reaction of cyclic olefins
    Xiaojin Wu
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371
    Chemistry 19:6014-20. 2013
    ..The desired isomers were produced by palladium-hydride-catalyzed isomerization of the initial products. Thus, a specific catalyst must be used so that it can perform two jobs under one set of reaction conditions...
  21. doi request reprint Gold-catalyzed cycloisomerization of 1,6-diyne carbonates and esters to 2,4a-dihydro-1H-fluorenes
    Weidong Rao
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore
    J Am Chem Soc 135:7926-32. 2013
    ....