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Theoretical pKa prediction of the α-phosphate moiety of uridine 5′-diphosphate-GlcNAc

Journal Article


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Abstract


  • The pKa value of the α-phosphate moiety of uridine 5'-diphosphate-GlcNAc (UDP-GlcNAc) has been successfully calculated using density functional theory methods in conjunction with the Polarizable Continuum Models. Theoretical methods were benchmarked over a dataset comprising of alkyl phosphates. B3LYP/6-31+G(d,p) calculations using SMD solvation model provide excellent agreement with the experimental data. The predicted pKa for UDP-GlcNAc is consistent with most recent NMR studies but much higher than what it has long been thought to be. The importance of this study is evident that the predicted pKa for UDP-GlcNAc supports its potential role as a catalytic base in the substrate-assisted biocatalysis.

Authors


  •   Vipperla, Bhavani Prasad (external author)
  •   Griffiths, Thomas M. (external author)
  •   Wang, Xingyong (external author)
  •   Yu, Haibo

Publication Date


  • 2017

Citation


  • Vipperla, B., Griffiths, T. M., Wang, X. & Yu, H. (2017). Theoretical pKa prediction of the α-phosphate moiety of uridine 5′-diphosphate-GlcNAc. Chemical Physics Letters, 667 220-225.

Scopus Eid


  • 2-s2.0-85004039820

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=1991&context=ihmri

Ro Metadata Url


  • http://ro.uow.edu.au/ihmri/966

Has Global Citation Frequency


Number Of Pages


  • 5

Start Page


  • 220

End Page


  • 225

Volume


  • 667

Place Of Publication


  • Netherlands

Abstract


  • The pKa value of the α-phosphate moiety of uridine 5'-diphosphate-GlcNAc (UDP-GlcNAc) has been successfully calculated using density functional theory methods in conjunction with the Polarizable Continuum Models. Theoretical methods were benchmarked over a dataset comprising of alkyl phosphates. B3LYP/6-31+G(d,p) calculations using SMD solvation model provide excellent agreement with the experimental data. The predicted pKa for UDP-GlcNAc is consistent with most recent NMR studies but much higher than what it has long been thought to be. The importance of this study is evident that the predicted pKa for UDP-GlcNAc supports its potential role as a catalytic base in the substrate-assisted biocatalysis.

Authors


  •   Vipperla, Bhavani Prasad (external author)
  •   Griffiths, Thomas M. (external author)
  •   Wang, Xingyong (external author)
  •   Yu, Haibo

Publication Date


  • 2017

Citation


  • Vipperla, B., Griffiths, T. M., Wang, X. & Yu, H. (2017). Theoretical pKa prediction of the α-phosphate moiety of uridine 5′-diphosphate-GlcNAc. Chemical Physics Letters, 667 220-225.

Scopus Eid


  • 2-s2.0-85004039820

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=1991&context=ihmri

Ro Metadata Url


  • http://ro.uow.edu.au/ihmri/966

Has Global Citation Frequency


Number Of Pages


  • 5

Start Page


  • 220

End Page


  • 225

Volume


  • 667

Place Of Publication


  • Netherlands