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

Authors

Bhavani Prasad Vipperla, University of WollongongFollow
Thomas M. Griffiths, University of WollongongFollow
Xingyong Wang, University of WollongongFollow
Haibo Yu, University of WollongongFollow

RIS ID

111454

Publication Details

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

Abstract

The pK_a 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 pK_a 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 pK_a for UDP-GlcNAc supports its potential role as a catalytic base in the substrate-assisted biocatalysis.

Grant Number

ARC/FT110100034

Grant Number

ARC/DP170101773