Enzyme-catalyzed aldol condensation for asymmetric synthesis of azasugars: synthesis, evaluation, and modeling of glycosidase inhibitors

…, RL Pederson, Z Zhong, Y Ichikawa…

Index: Kajimoto, Tetsuya; Liu, Kevin K.-C.; Pederson, Richard L.; Zhong, Ziyang; Ichikawa, Yoshitaka; Porco Jr., John A.; Wong, Chi-Huey Journal of the American Chemical Society, 1991 , vol. 113, # 16 p. 6187 - 6196

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Citation Number: 290

Abstract

Abstract: A combined fructose 1, 6diphosphate aldolase reaction and catalytic reductive amination has been used in the asymmetric synthesis of azasugars structurally corresponding to N-acetylglucosamine, N-acetylmannosamine, and deoxyhexoses. The 6- deoxyazasugars were prepared by direct hydrogenolysis of the aldolase product without removal of the 6-phosphate group. Both (R)-and (S)-3-azido-2-acetamidopropanal used ...

~26%

~91%

A facile transformation of sugar lactones to azasugars

[Overkleeft, Herman S.; Wiltenburg, Jim van; Pandit, Upendra K. Tetrahedron, 1994 , vol. 50, # 14 p. 4215 - 4224]

Synthesis of deoxynojirimycin and of nojirimycin δ-lactam

[Fleet, George W.J.; Carpenter, Neil M.; Petursson, Sigthor; Ramsden, Nigel G. Tetrahedron Letters, 1990 , vol. 31, # 3 p. 409 - 412]