Journal of Organic Chemistry p. 6280 - 6289 (1991)
Update date:2022-08-04
Topics:
Liu, Kevin K.-C.
Kajimoto, Tetsuya
Chen, Lihren
Zhong, Ziyang
Ichikawa, Yoshitaka
Wong, Chi-Huey
The use of fructose-1,6-diphosphate (FDP), fuculose-1-phosphate (Fuc-1-P) and rhamnulose-1-phosphate (Rham-1-P) aldolases in organic synthesis is described.Fuc-1-P, Rham-1-P, and their phosphate-free species have been prepared and characterized.Both Fuc-1-P and Rham-1-P aldolases accept 3-azido-2-hydroxypropanal as a substrate to form L-ω-azidoketose phosphates, which upon dephosphorylation and hydrogenolysis on Pd/C, gave 1-deoxyazasugars structurally related to D-galactose and L-mannose.Hydrogenolysis of the enzyme products azidoketose 1-phosphates, however, gave 1,6-dideoxyazasugars structurally related to 6-deoxygalactose and L-rhamnose.Explanations for the stereoselectivity in the hydrogenolysis reactions were provided.Similarly, FDP aldolase catalyzed the aldol condensation reaction with 2-azido-3-hydroxypropanal to afford a new synthesis of 2(R),5(S)-bis(hydroxymethyl)-3(R),4(R)-dihydroxypyrrolidine, a potent inhibitor of a number of glycosidases.A new empirical formula is developed to relate the inhibition constants and inhibitor binding for α- and β-glucosidases.
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