82040-50-4Relevant academic research and scientific papers
Stereoselective synthesis of thioxylooligosaccharides from S-glycosyl isothiourea precursors
Ibatullin, Farid M,Shabalin, Konstantin A.,J?nis, Janne V.,Selivanov, Stanislav I.
, p. 4565 - 4567 (2007/10/03)
A stereoselective synthesis of thioxylo-di-, -tri-, -tetra- and -penta-saccharides from S-glycosyl isothiourea precursors is described. The synthesis was performed starting from 2,3,4-tri-O-acetyl-β-D-xylopyranosyl isothiouronium bromide using a triethylamine promoted reaction with 1,2,3-tri-O-benzoyl-4-O-trifluoromethanesulphonyl-β-L-arabinopyranose. The resulting 4-thioxylobiose was then converted into the corresponding isothiouronium bromide and used for the synthesis of 4,4′-dithioxylotriose. Higher homologues of the series and their α-methyl glycosides were also prepared.
Positional isomers of thioxylobiose, their synthesis and inducing ability for D-xylan-degrading enzymes in the yeast Cryptococcus albidus
Defaye,Guillot,Biely,Vrsanska
, p. 47 - 64 (2007/10/02)
Isomeric S-linked 2-thioxylobiose 10, 3-thioxylobiose 17, and 4-thioxylobiose 19 were conveniently prepared by SN2 displacement of suitable triflylglycoses with the sodium salt of 2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranose, either in N,N-dimethylformamide, or in oxolan in the presence of a sodium complexing agent. Allyl 3,5-O-isopropylidene-2-O-trifluoromethanesulfonyl-β-D-lyxofuranoside was a convenient electrophilic precursor for 10, which was smoothly obtained after a short sequence of deprotection involving conversion to the 1-propenyl glycoside. 1,2:5,6-Di-O-isopropylidene-3-O-trifluoromethylsulfonyl-α-D-allofuran ose and 1,2,3-tri-O-benzoyl-4-O-trifluoromethylsulfonyl-β-L-arabinopyranose were the respective precursors for 17 and 19. 4-Thioxylobiose has a highly stimulatory effect on the synthesis of enzymes of the xylanolytic system in the yeast Cryptococcus albidus when applied to the cells in the presence of the natural disaccharide inducer (1→4)-β-D-xylobiose. Isomeric S-linked 2-thioxylobiose 10, 3-thioxylobiose 17, and 4-thioxylobiose 19 were conveniently prepared by SN2 displacement of suitable triflylglycoses with the sodium salt of 2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranose, either in N,N-dimethylformamide, or in oxolan in the presence of a sodium complexing agent. Allyl3,5-O-isopropylidene-2-O -trifluoromethanesulfonyl -β-D-lyxofuranoside was a convenient electrophilic precursor for 10, which was smoothly obtained after a short sequence of deprotection involving conversion to the 1-propenyl glycoside, 1,2:5,6-Di-O-isopropylidene-3-O -trifluoromethylsulfonyl-α-D- allofuranose and 1,2,3-tri-O-benzoyl-4-O -trifluoromethylsulfonyl -β-1,-arabinopyta nose were the respective precursors for 17 and 19.4-Thioxylobiose has a highly stimulatory effect on the synthesis of enzymes of the xylanolytic system in the yeast Cryptococcus albidus when applied to the cells in the presence of the natural disaccharide inducer (1→4)-β-D-xylobiose.
INDUCTION OF D-XYLAN-DEGRADING ENZYMES IN Trichoderma lignorum BY NONMETABOLIZABLE INDUCERS. A SYNTHESIS OF 4-THIOXYLOBIOSE
Defaye, Jacques,Driguez, Hugues,John, Michael,Schmidt, Juergen,Ohleyer, Eric
, p. 123 - 132 (2007/10/02)
The D-xylan degrading enzymes of Trichoderma lignorum can be induced by several oligo- and poly-saccharides.The induction is optimal when L-arabino-D-xylan is used as carbon source.The enzymes were also produced by cells grown on glycerol in the presence of 4-thioxylobiose (4-S-β-D-xylopyranosyl-4-thio-D-xylopyranose)and methyl β-D-xylopyranoside.These inducers were not taken up by the cells.The extent of induction was, however, lower than with xylobiose.Thioxylobiose was obtained in an overall yield of 55-60percent from the reaction of 1,2,3-tri-O-benzoyl-4-O-trifluoromethylsulfonyl-β-L-arabinopyranose with the sodium salt of 1-thio-β-D-xylopyranose in N',N'',N'''-hexamethylphosphoramide, followed by O-deacylation of the resulting 4-thiodisaccharide.
