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PubMed1990

Energy-rich glyceric acid oxygen esters: implications for the origin of glycolysis.

The apparent Gibbs free energy change of hydrolysis (delta G degrees', pH 7) of the 2- and 3-O-glyceroyl esters of 2- and 3-O-L-glyceroyl-L-glyceric acid methyl ester were measured at 25 degrees C. The 2- and 3-glyceroyl esters were found to be 'energy-rich' with delta G degrees' values of -9.1 kcal mol-1 and -7.8 kcal mol, respectively. This result indicates that the analogous 2- and 3-glyceroyl esters of polyglyceric acid are also 'energy-rich' and, therefore, could have acted as an energy source for primitive phosphoanhydride synthesis.

Energy Metabolism↗
PubMed1996

A method for determination of the absolute configuration of chiral glycerol residues in natural products using TEMPO oxidation and characterization of the glyceric acids formed.

A method has been developed for determination of the absolute configuration of glycerol residues in natural products. It is required that the glycerol moiety contain a primary nonsubstituted hydroxymethyl group or that such a group can be obtained by modification without racemization. The method employs TEMPO oxidation of the primary hydroxyl group, hydrolysis, butanolysis with chiral 2-butanol, and acetylation. The acetylated (+)-2-butyl esters of the glyceric acid formed by oxidation are analyzed by gas-liquid chromatography. The esterification can also be performed with other chiral alcohols, e.g., (-)-2-octanol. The method is general and applicable to both primary and secondary substituted glycerols. It has recently been used for determination of the chiral glycerol-1-phosphate residue of the Escherichia coli O28 O-antigen, and now we report the absolute configurations of the glycerol moieties in Streptococcus pneumoniae type 18A and Streptococcus agalactaie type III. All studied glycerol residues were found to have the D-configuration.

Carbohydrate Sequence↗
PubMed2003

Crystal structure of Trypanosoma cruzi glyceraldehyde-3-phosphate dehydrogenase complexed with an analogue of 1,3-bisphospho-d-glyceric acid.

We report here the first crystal structure of a stable isosteric analogue of 1,3-bisphospho-d-glyceric acid (1,3-BPGA) bound to the catalytic domain of Trypanosoma cruzi glycosomal glyceraldehyde-3-phosphate dehydrogenase (gGAPDH) in which the two phosphoryl moieties interact with Arg249. This complex possibly illustrates a step of the catalytic process by which Arg249 may induce compression of the product formed, allowing its expulsion from the active site. Structural modifications were introduced into this isosteric analogue and the respective inhibitory effects of the resulting diphosphorylated compounds on T. cruzi and Trypanosoma brucei gGAPDHs were investigated by enzymatic inhibition studies, fluorescence spectroscopy, site-directed mutagenesis, and molecular modelling. Despite the high homology between the two trypanomastid gGAPDHs (> 95%), we have identified specific interactions that could be used to design selective irreversible inhibitors against T. cruzi gGAPDH.

Animals↗