Yohji Ezure

Effect of dissolved oxygen and pH on moranoline (1-deoxynojirimycin) fermentation by Streptomyces lavendulae

Abstract The intent of this work was to investigate the effects of control of DO and pH on moranoline (1-deoxynojirimycin) production by Streptomyces lavendulae for large-scale moranoline fermentation. The conclusions reached are as follows: (i) It is most important to maintain DO at 20% saturation from the stage of fermentation when the rate of DO consumption is high. (ii) When the DO is maintain between 20 and 85% saturation, it is important to maintain pH at less than 7. When the fermentation was carried out so as to maintain the DO at 20% saturation in a 30 l fermentor, 10.2–10.5 g· l −1 of moranoline was produced.

AN EFFICIENT SYNTHESIS OF SULFO LEWIS X ANALOG CONTAINING 1-DEOXYNOJIRIMYCIN

Abstract Sulfo Lewisx analog containing 1-deoxynojirimycin (13) has been efficiently synthesized. Glycosidation of ethyl 2,3,4-tri-O-benzyl-1-thio-β-D-fucopyranoside (5) with O-2,6-di-O-benzoyl-3,4-isopropylidene-β-D-galactopyranosyl)-(1→4)-2,6-di-O-benzoyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol (4), prepared from O-β-D-galactopyranosyl-(1→4)-1,5-dideoxy-1,5-imino-D-glucitol (1) via 3 steps, and subsequent acid hydrolysis of the isopropylidene group gave the desired trisaccharide diol derivative (7) in good yield. Compound 7 was easily converted into 3′-O-sulfo Lewisx analog (13) via 6 steps in high yield. 1. Dedicated to the memory of Professor Akira Hasegawa.

Enzymatic Synthesis of 4-O-α-d-Glucopyranosyl-moranoline

A transglycosylation reaction with moranoline (1-deoxynojirimycin) was carried out with α-cyclodextrin as the glucose donor and Bacillus macerans amylase as cyclodextrin glycosyltransferase [EC 2.4.1.19]. The resultant transglycosylation products were hydrolyzed by glucoamylase [EC 3.2.1.3] from Rhizopus niveus. The hydrolyzate (the transglycosylation product of the lowest molecular weight) was isolated and the structure was found by physico-chemical methods to be 4-O-α-d-glucopyranosyl-moranoline.