Enzymatic glycosidation

J. D. McCarter and S. G. Withers, Mechanisms of enzymatic glycoside hydrolysis, Curr. Opin. Struct. Biol, 4 (1994) 885-892. 

McCarter, J. and Withers, S. (1994) Mechanisms of enzymatic glycoside hydrolysis. 

GeloPujic, M., Guibejampel, E., Loupy, A. and Trincone, A., Enzymatic glycosidation in dry media under microwave irradiation,/. Chem. Soc., Perkin Trans. 1, 1997, 1001. 

Lactose, phenylosotriazole, III, 38 a-Lactose, acetochloro-, I, 40, 41 Lactyl chloride, acetyl-, III, 367 Laminarin, IV, 275, 282 Langenbeck s formulation of enzymatic glycoside hydrolysis, V, 58 Larch, e-galactan of, II, 249 Larch manna. See Manna. 

Berti PJ, Tanaka KSE (2002) Transition state analysis using multiple kinetic isotope effects mechanisms of enzymatic and non-enzymatic glycoside hydrolysis and transfer. Adv. Phys. Org. Chem. 37 239-314... 

Melilotus officinalis (sweet clover) contains coumarin, 3,4-dihydrocoumarin (melilotine), ortho-coumaric acid, ortho-hydroxycoumaric acid, and the ortho-glucoside of ortho-coumaric acid (melilotoside). Withering of the plant leads to enzymatic glycoside hydrolysis and the resulting ortho-coumaric acid is spontaneously transformed to coumarin the dried herb therefore smells strongly of coumarin (see separate monograph). M. officinalis has been used to treat lymphedema and the edema of chronic venous insufficiency. 

Transition State Analysis Using Multiple Kinetic Isotope Effects Mechanisms of Enzymatic and Non-enzymatic Glycoside Hydrolysis and Transfer... 

We discuss in this chapter how TS analysis allows chemists to ask sophisticated and subtle questions of enzymatic and non-enzymatic glycoside hydrolysis and transfer reactions. It is now becoming possible to measure routinely (if perhaps not... 

The two canonical mechanisms of enzymatic glycoside hydrolysis were first proposed by Koshland in 1953. Since then, considerable amounts of structural and mechanistic data have been accumulated in support of the proposed mechanisms, both of which involve nucleophilic displacement steps. The reactions result in either net (1) inversion, or (2) retention of the substrate anomeric configuration." " " The following section provides an account of these two basic mechanistic groups of enzymes. 

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