162088-89-3Relevant academic research and scientific papers
Glycosynthase-Mediated Assembly of Xylanase Substrates and Inhibitors
Goddard-Borger, Ethan D.,Fiege, Brigitte,Kwan, Emily M.,Withers, Stephen G.
experimental part, p. 1703 - 1711 (2012/06/29)
An exo-β-xylosidase mutant with glycosynthase activity was created to aid in the synthesis of xylanase substrates and inhibitors. Simple monosaccharides were easily elaborated into di-, tri- and tetrasaccharides by using this enzyme. Some products proved
An efficient chemical-enzymatic synthesis of 4-nitrophenyl β- xylobioside: A chromogenic substrate for xylanases
Mechaly, Adva,Belakhov, Valery,Shoham, Yuval,Baasov, Timor
, p. 111 - 115 (2007/10/03)
4-Nitrophenyl-β-xylobioside was synthesized by an improved short chemical-enzymatic method, based on the use of xylobiose as a starting material. Xylobiose was prepared following extensive enzymatic digestion of birchwood xylan with xylanase T-6. The resulting digest, containing mainly xylobiose and xylose, was directly subjected to an acetylation step, which after silica gel chromatography, provided highly pure hexaacetate of xylobiose. Bromination with HBr in acetic acid gave in quantitative yields the corresponding bromide, which after the coupling and deprotection steps, afforded the target 4-nitrophenyl-β-xylobioside.
Synthesis of 2- and 4-nitrophenyl β-glycosides of β-(1 → 4)-D-xylo-oligosaccharides of dp 2-4
Takeo,Ohguchi,Hasegawa,Kitamura
, p. 231 - 244 (2007/10/03)
2- and 4-Nitrophenyl β-D-xylopyranosides (4 and 5) were transformed, via dibutyltin oxide-mediated acylation, into the corresponding 2,3-di-O-benzoyl derivatives 11 and 15. Xylobiose and xylotriose were easily isolated by charcoal column chromatography from a commercially available material and converted into the di- and trisaccharide methyl 1-thio-β-glycosides 36 and 37. The 2- and 4-nitrophenyl β-glycosides of the β-(1 → 4)-D-xylo-oligosaccharides of dp 2-4 were synthesized by N-iodosuccinimide-silver triflate-promoted condensation using 11 and 15 as the glycosyl acceptors and ethyl 1-thio-β-D-xylopyranoside triacetate 16, 36, and 37 as the glycosyl donors. Also described are an improved preparation of 4 and 5, and the synthesis of 1-naphthyl β-D-xylopyranoside, as well as an alternative approach to the 2- and 4-nitrophenyl β-xylobiosides.
A short synthesis of β-xylobiosides
Ziser, Lothar,Withers, Stephen G.
, p. 9 - 18 (2007/10/02)
Benzyl 2,3,2',3',4'-penta-O-acetyl-β-xylobioside, 2-nitrophenyl β-xylobioside, 4-nitrophenyl β-xylobioside, and 2-iodobenzyl 1-thio-β-xylobioside were synthesized via a short and highly selective route. β-D-Xylopyranosides were selectively 4-O-triethylsil
