126252-57-1Relevant articles and documents
1-O-Acetyl-β-D-galactopyranose: A novel substrate for the transglycosylation reaction catalyzed by the β-galactosidase from Penicillium sp.
Zinin, Alexander I.,Eneyskaya, Elena V.,Shabalin, Konstantin A.,Kulminskaya, Anna A.,Shishlyannikov, Sergei M.,Neustroev, Kirill N.
, p. 635 - 642 (2002)
1-O-Acetyl-β-D-galactopyranose (AcGal), a new substrate for β-galactosidase, was synthesized in a stereoselective manner by the trichloroacetimidate procedure. Kinetic parameters (KM and kcat) for the hydrolysis of 1-O-acetyl-β-D-galactopyranose catalyzed by the β-D-galactosidase from Penicillium sp. were compared with similar characteristics for a number of natural and synthetic substrates. The value for kcat in the hydrolysis of AcGal was three orders of magnitude greater than for other known substrates. The β-galactosidase hydrolyzes AcGal with retention of anomeric configuration. The transglycosylation activity of the β-D-galactosidase in the reaction of AcGal and methyl β-D-galactopyranoside (1) as substrates was investigated by 1H NMR spectroscopy and HPLC techniques. The transglycosylation product using AcGal as a substrate was β-D-galactopyranosyl-(1→6)-1-O-acetyl-β-D-galactopyranose (with a yield of ～70%). In the case of 1 as a substrate, the main transglycosylation product was methyl β-D-galactopyranosyl-(1→6)-β-D-galactopyranoside. Methyl β-D-galactopyranosyl-(1→3)-β-D-galactopyranoside was found to be minor product in the latter reaction.
Applications of Shoda's reagent (DMC) and analogues for activation of the anomeric centre of unprotected carbohydrates
Fairbanks, Antony J.
, (2020/12/07)
2-Chloro-1,3-dimethylimidazolinium chloride (DMC, herein also referred to as Shoda's reagent) and its derivatives are useful for numerous synthetic transformations in which the anomeric centre of unprotected reducing sugars is selectively activated in aqueous solution. As such unprotected sugars can undergo anomeric substitution with a range of added nucleophiles, providing highly efficient routes to a range of glycosides and glycoconjugates without the need for traditional protecting group manipulations. This mini-review summarizes the development of DMC and some of its derivatives/analogues, and highlights recent applications for protecting group-free synthesis.
Use of human-milk fucosyltransferase in the chemoenzymic synthesis of analogues of the sialyl Lewisx and sialyl Lewisa tetrasaccharides modified at the C-2 position of the reducing unit
Nikrad, Pandurang V.,Kashem, Mohammed A.,Wlasichuk, Kenneth B.,Alton, Gordon,Venot, Andre P.
, p. 145 - 160 (2007/10/02)
Two series of trisaccharides, having the formulas α-Neu5Ac-(2->3)-β-D-Gal-(1->4)-β-D-GlcZ-OR and α-Neu5Ac-(2->3)-β-D-Gal-(1->3)-β-D-GlcZ-OR respectively, in which the 2-deoxy substituent Z is azido, amino, propionamido, or acetamido, were
