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Enzymic glycosylation of (±)-(3,5/4,6)-3,6-diazido-4,5-dihydroxycyclohexene. A way to prepare stereochemically pure and enzyme resistant, basic pseudo-disaccharides as competitive enzyme inhibitors

Authors
Journal
Carbohydrate Research
0008-6215
Publisher
Elsevier
Publication Date
Volume
276
Issue
1
Identifiers
DOI: 10.1016/0008-6215(95)00132-d
Keywords
  • β-D-Galactosidase
  • Pseudo-Disaccharides
  • Competitive Inhibition
  • Stereospecific Glycosylation

Abstract

Abstract By β- d-galactosylation of (±)-(3,5/4,6)-3,6-diazido-4,5-dihydroxycyclohexene, pure (+)-(3,5/4,6)-3,6- diazido-4-O-(β- d-galactopyranosyl)-5-hydroxycyclohexene ( 3) was obtained. The diamine (+)-(1,3/2,6)-3,6- diamino-1-O-(β- d-galactopyranosyl)-2-hydroxycyclohexane , derived from compound 3 by catalytic hydrogenation, is stable against enzymic cleavage and competitively inhibits β- d-galactosidase from Escherichia coli with a K i- value of 5.5 mM. Sigmatropic rearrangement of 3 in methanolic solution partially led to an unseparable mixture of the regioisomers (3,5/4,6)-3,4- diazido-5-O-(β- d-galactopyranosyl)-6-hydroxycyclohexene and (3,5/4,6)-3,4- diazido-6-O-(β- d-galactopyranosyl)-5-hydroxycyclohexene . Catalytic hydrogenation thereof yielded an equally unseparable mixture of the diamines (1,3/2,4)-1,2- diamino-3-O-(β- d-galactopyranosyl)-4-hydroxycyclohexane and (1,3/2,4)-1,2- diamino-4-O-(β- d-galactopyranosyl)-3-hydroxycyclohexane , inhibiting β- d-galactosidase competitively with K i 0.9 mM.

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