Glucoside synthesis

Tattersall, D. B., Bak, S., Jones, P. R., etal. (2001). Resistance to an herbivore through engineered cyanogenic glucoside synthesis. Science 293,1826-1828. 

In this laboratory we have had partial success with the hydroboration of the model compound and from it have obtained methyl a-D-gluco-pyranoside, but the procedures require further development before a new, satisfactory a-glucoside synthesis can be claimed. 

Alluis, B. and Dangles, O., Acylated flavone glucosides synthesis, conformational investigation and complexation properties, Helv. Chim. Acta, 82, 2201, 1999. 

We tested a number of dicot species for their ability to detoxify BOA. Most of them were incubated as seedlings but some as adult plants when germination failed under laboratory conditions. Applied BOA concentration was 100 and 500 pM, incubation time was 24 h. The plants were separated into roots and shoots after incubation and the material extracted with 30% methanol. HPLC analyses of the extracts revealed remarkable differences in the detoxification capacities. Major detoxification appeared within the roots, whereas shoots were only involved when roots seemed to be overtaxed. All species tested were able to perform BOA-6-O-glucoside synthesis, but with regard to glucoside carbamate synthesis, differences became obvious (Table 4.2). 

Laroute V, Willemot RM. Glucoside synthesis by glucoamylase or glucosidase in organic solvents. Biotechnol. Lett. 1992 14 169-174. 

Lirdprapamongkol K, Svasti J. Alkyl glucoside synthesis using Thai rosewood beta-glucosidase. Biotechnol. Lett. 2000 22 1889-1894. 

Frechet, J M, Schuerch, C, Solid-phase synthesis of oligosaccharides. 2. Steric control by C-6 substituents in glucoside synthesis, J. Am. Chem. Soc., 94, 604-609, 1972. 

On principle, the benzoxazinone glucoside synthesis has the same challenge, but there is no asymmetric induction from the aglucone unit. 

R. Eby and C. Schuerch, The use of positively charged leaving-groups in the synthesis of a-D-linked glucosides. Synthesis of methyl 2,3,4-tri-0-benzyl-6-0-(2,3,4,6-tetra-0-benzyl-a-D-glucopyranosyl)-a-D-glucopyranoside, Carbohydr. Res., 39 (1975) 33-38. 

Potential of Native Sucrose-Utilizing Transglucosidases for Glucoside Synthesis... 

Glucoside synthesis in the presence of high concentration of ethanol or acetone described. Bourquelot, B ridel and Verdon... 

The enzymes catalyzing the subsequent steps in cyanogenic glucoside synthesis, that is, the conversion of oximes into cyanohydrins are not nearly as substrate specific. Again this knowledge was... 

Benn, M.H. A new mustard oU glucoside synthesis The synthesis of glucotropaeolin. Canadian Journal of Chemistry, 41(11), 2836-2838.1963. 

Ruhmann, S. et ak (2006) Piceid (resveratrol glucoside) synthesis in stilbene synthase transgenic apple fruit. J. Agri. Food Chem. 54, 4633 640... 

Vulfson, E. N., Patel, R., Beecher, J. E. et al. (1990) Glycosidases in organic solvents I. Alkyl-6-glucoside synthesis in a water-organic two-phase system. Enzyme Microb. TechnoL, 12, 950-954. 

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