L-Glycerate

Rashed, M.S. et al., Chiral liquid chromatography tandem mass spectrometry in the determination of the configurations of glyceric acid in urine of patients with D-glyceric and L-glyceric acidurias, Biomed. Chromatogr, 16, 191, 2002. 

Optically pure D- and L-glyceric adds were made by cleavage of vicinal diols or of a-hydroxy acids by RuCyaq. Na(C10) pH 8 (Fig. 4.6) [398], The system RuCyaq. Na(IOyCH3CN-CCl oxidised PhCMeCH(0H)CH20H to PhCMeCOOH [260], and RuCyaq. Na(ClO)/0°C converted 1,2-dihydroxycyclohexane to adipic add [35,256]. 

D-Glyceric acid (or D-2,3-dihydroxypropanoic acid C3H604, MW = 125.10) is a hydroxy acid derived from the oxidation of Cl of glycerol or glyceraldehyde to a carboxyl group various phosphorylated derivatives of L-glycerate are important intermediates in glucose metabolism (Fig. 3.5.3). 

At the time the choice of absolute configuration for glyceraldehyde was made, there was no way of knowing whether the configuration of (-l-)-glycer-aldehyde was in reality 3a or 3b. However, the choice had a 50% chance of... 

BENZYL-L-GLYCER ALDEHYDE AND ETHYL (R,E)-4-0-BENZYL-4.5-DIHYDROXY-2-PENTENOATE (Propanal, 3-hydroxy-2-(phenylmethoxy)-, (R)- and 2-Pentenoic acid, 5-hydroxy-4-(phenylmethoxy)-, ethyl ester, [R-(E)]-)... 

The polyhydric alcohols, ranging from glycerol to the hexitols (XVII), can also be oxidized, the products including both aldoses and ketoses. As the reaction mixtures are generally resolved as the phenylosazones, only a limited distinction between the products results. In the case of glycerol, n,L-glyceric acid and degradation products are also formed. 

In the case of the oxidation of glycerol, D,L-glyceric acid has also been isolated. Hlasiwetz and Habermann treated glycerol with chlorine water and obtained the acid as the main product. From the action of bromine water on glycerol, Barth obtained glyceric acid, bromoform and carbon dioxide. In the absence of water, bromine converted glycerol to dibromohydrin and bromoacetic acid. The former decomposed to hydrogen bromide and acrolein. 

L-glyceric aciduria (Primary hyperoxaluria Type II) L-glyceric, oxalic... 

Gellan gum (60) was found to be specifically cleaved by hydrogen fluoride at —40° at the a-L-rhamnosyl linkage, to generate the tetrasaccharide 61 which was partially acetylated but also acylated by L-glyceric acid. Treatment at —23° afforded the trisaccharide fluoride 62, which was also acylated. Some loss of glycerate, and possibly of acetate, occurred during the... 

Imidazolidine derivative 9 was obtained by the borohydride reduction of the corresponding A2-imidazolinium cation precursor formed by the condensation of the acetonide of the ethyl ester of D,L-glyceric acid and 1,1-dimethyl-1,2-diamine followed by acetylation and methylation (80H947, 83T3987). 

Reticuline labeled with tritium was used in experiments to show 29) that thebaine (and consequently also codeine and morphine) arises from (— )-reticuline, which is in agreement with the known absolute configuration of these morphinane bases. Its intermediate is salutaridinol-I (not its epimer II) where the absolute configuration of the hydroxyl group was determined by isolation of L-glyceric acid (after degradation). 

The prefix "D" tells us that D-ribose belongs to the same optical family as D-glyceraldehyde. The other stereoisomer, L-ribose, would be related to L-glycer-aldehyde. Note that the symbols D and L refer to configuration, and not to sign of rotation. 

---