PMID: 209459May 1, 1978

Adenosine 5'-O-([gamma-18O]gamma-thio)triphosphate chiral at the gamma-phosphorus: stereochemical consequences of reactions catalyzed by pyruvate kinase, glycerol kinase, and hexokinase

Proceedings of the National Academy of Sciences of the United States of America
G A OrrJ R Knowles

Abstract

The 2-[18O]phosphorothioate of D-glycerate, chiral at phosphorus, was prepared. The chiral phosphoryl group was transferred enzymically to ADP [by using enolase and pyruvate kinase (ATP:pyruvate 2-O-phosphotransferase; EC 2.7.1.40)] resulting in the synthesis of adenosine 5'-O-([gamma-18O],gamma-thio)triphosphate. This labeled ATP was used as a thiophosphoryl group donor in the reactions catalyzed by glycerol kinase (ATP:glycerol 3-phosphotransferase; EC 2.7.1.30) and by hexokinase (ATP:D-hexose 6-phosphotransferase; EC 2.7.1.1). The product from the latter (glucose 6-phosphorothioate) was converted enzymically into glycerol phosphorothioate. Determination of the relative configurations and diastereoisomeric purities of the samples of glycerol phosphorothioate demonstrates that all three phosphokinases (pyruvate kinase, glycerol kinase, and hexokinase) transfer the thiophosphoryl group with complete stereospecificity, and further shows that these reactions follow an identical stereochemical course.

References

Mar 13, 1981·Molecular and Cellular Biochemistry·T Nowak, C Suelter
Dec 1, 1981·Proceedings of the National Academy of Sciences of the United States of America·S D PutneyP R Schimmel
Jul 1, 2010·Biometals : an International Journal on the Role of Metal Ions in Biology, Biochemistry, and Medicine·Marzena Wojcik, Wojciech J Stec
Jun 30, 1980·Biochemical and Biophysical Research Communications·J P RichardP A Frey
May 30, 1980·Biochemical and Biophysical Research Communications·I A Rose
Feb 23, 1988·Biochemistry·K D Sikkema, M H O'Leary
Feb 21, 1989·Biochemistry·J A Peliska, M H O'Leary

Citations

Jun 18, 1974·Biochemical and Biophysical Research Communications·D Gratecos, E H Fischer
Jan 1, 1972·Annual Review of Biochemistry·J F Morrison, E Heyde

Related Concepts

Molecular Stereochemistry
Glycerin
Adenosine
Pyruvate Measurement
Pyruvate Kinase
Phosphate Measurement
Glycerol Kinase
Hexokinase
Phosphorus Measurement
Pyruvate

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