7472-25-5Relevant academic research and scientific papers
Substrate Specificity and Carbohydrate Synthesis Using Transketolase
Kobori, Yoshihiro,Myles, David C.,Whitesides, George M.
, p. 5899 - 5907 (2007/10/02)
This paper describes the use of the enzyme transketolase as a catalyst in organic synthesis.The properties of transketolase from both yeast and spinach were investigated.The yeast enzyme was found to be more convenient for routine use.Examination of the substrate specificity of yeast tansketolase demonstrated that the enzyme accepts a wide variety of 2-hydroxy aldehydes as substrates.A practical protocol for tansketolase-catalyzed condensation of hydroxypyruvic acid with these aldehydes has been developed and used for the synthesis of four carbohydrates: L-idose, L-gulose, 2-deoxy-L-xylohexose, and L-xylose.
Chemical and Enzymatic Syntheses of 6-Deoxyhexoses. Conversion to 2,5-Dimethyl-4-hydroxy-2,3-dihydrofuran-3-one (Furaneol) and Analogues
Wong, Chi-Huey,Mazenod, Francois P.,Whitesides, George M.
, p. 3493 - 3497 (2007/10/02)
6-Deoxy-D-fructose 1-phosphate (6-deoxyF-1-P) forms when a solution containing D-fructose 1,6-diphosphate (FDP) and D-lactaldehyde is treated with the enzymes aldolase and triosephosphate isomerase (Scheme I).This transformation involves three reactions: aldolase-catalyzed cleavage of FDP to a mixture of dihydroxyacetone phosphate and D-glyceraldehyde phosphate, triosephosphate isomerase catalyzed equilibration of dihydroxyacetone phosphate and D-glyceraldehyde phosphate, and aldolase-catalyzed condensation of dihydroxyacetone phosphate and D-lactaldehyde to 6-deoxyF-1-P.An analogous process converts a mixture of FDP and L-lactaldehyde to 6-deoxysorbose 1-phosphate (6-deoxyS-1-P).Aldolase-catalyzed reaction of dihydroxyacetone phosphate, prepared separately, with D-lactaldehyde yields 6-deoxyF-1-P directly; similar reaction of dihydroxyacetone phosphate with α-hydroxybutyraldehyde yields a mixture of 6-methyl-6-deoxyhexose 1-phosphates.Acid-catalyzed hydrolysis of the sugar phosphates releases the corresponding free sugars.A mixture containing 6-deoxyhexoses is formed directly by base-catalyzed aldol condensation of dihydroxyacetone and D,L-lactaldehyde.Treatment of any of the 6-deoxyhexoses with acids generates 2,5-dimethyl-4-hydroxy-2,3-dihydrofuran-3-one (Furaneol, a flavor principle).Furaneol can also be prepared in moderate yields by hydrogenolysis of FDP and other hexose phosphates in alkaline media.
