Stereochemistry of an alpha, beta-elimination reaction by D-glucosaminate dehydratase. 1983

R Iwamoto, and Y Imanaga, and S Sawada, and K Soda

The proton NMR analysis of D-glucosaminate dehydratase reaction in D2O revealed the incorporation of a deuterium atom at C-3 carbon of the product, 2-keto-3-deoxy-D-gluconate. Based on the chemical shift of C-3 proton of the product and the coupling constant characteristic for the C-3 and C-4 axial-axial coupling in the 2C5 pyranose conformation, the deuterium is in the pro-S position. Thus, the dehydration of D-glucosaminate by the enzyme proceeds in a retention mode at C-3 carbon. Kinetic parameters show that the rate-determining step is the abstraction of alpha-proton from the substrate.

UI MeSH Term Description Entries
D007700 Kinetics The rate dynamics in chemical or physical systems.
D008968 Molecular Conformation The characteristic three-dimensional shape of a molecule. Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D003903 Deuterium The stable isotope of hydrogen. It has one neutron and one proton in the nucleus. Deuterons,Hydrogen-2,Hydrogen 2
D005942 Gluconates Derivatives of gluconic acid (the structural formula HOCH2(CHOH)4COOH), including its salts and esters. Copper Gluconate,Gluconate, Copper
D005944 Glucosamine 2-Amino-2-Deoxyglucose,Dona,Dona S,Glucosamine Sulfate,Hespercorbin,Xicil,2 Amino 2 Deoxyglucose,Sulfate, Glucosamine
D006836 Hydro-Lyases Enzymes that catalyze the breakage of a carbon-oxygen bond leading to unsaturated products via the removal of water. EC 4.2.1. Dehydratase,Dehydratases,Hydrase,Hydrases,Hydro Lyase,Hydro-Lyase,Hydro Lyases,Lyase, Hydro,Lyases, Hydro
D012231 Rhizobium A genus of gram-negative, aerobic, rod-shaped bacteria that activate PLANT ROOT NODULATION in leguminous plants. Members of this genus are nitrogen-fixing and common soil inhabitants.

Related Publications

R Iwamoto, and Y Imanaga, and S Sawada, and K Soda
April 2003, Biochimica et biophysica acta,
R Iwamoto, and Y Imanaga, and S Sawada, and K Soda
March 1995, Bioscience, biotechnology, and biochemistry,
R Iwamoto, and Y Imanaga, and S Sawada, and K Soda
January 1993, Bioscience, biotechnology, and biochemistry,
R Iwamoto, and Y Imanaga, and S Sawada, and K Soda
April 1990, Carbohydrate research,
R Iwamoto, and Y Imanaga, and S Sawada, and K Soda
January 2005, The Journal of biological chemistry,
R Iwamoto, and Y Imanaga, and S Sawada, and K Soda
March 2000, Biochemistry,
R Iwamoto, and Y Imanaga, and S Sawada, and K Soda
March 1962, Biochemistry,
R Iwamoto, and Y Imanaga, and S Sawada, and K Soda
May 2009, Biotechnology letters,
R Iwamoto, and Y Imanaga, and S Sawada, and K Soda
January 1980, Analytical biochemistry,
Copied contents to your clipboard!