210281-92-8

Basic information

• Product Name: phenyl β-D-galactopyranosyl-(1->3)-1-thio-β-D-glucopyranoside
• Synonyms: phenyl β-D-galactopyranosyl-(1->3)-1-thio-β-D-glucopyranoside
• CAS NO: 210281-92-8
• Molecular Weight: 434.464
• Mol File: 210281-92-8.mol

Chemical Properties

• CAS DataBase Reference: phenyl β-D-galactopyranosyl-(1->3)-1-thio-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl β-D-galactopyranosyl-(1->3)-1-thio-β-D-glucopyranoside(210281-92-8)
• EPA Substance Registry System: phenyl β-D-galactopyranosyl-(1->3)-1-thio-β-D-glucopyranoside(210281-92-8)

Safety Data

• Hazardous Substances Data: 210281-92-8(Hazardous Substances Data)

Upstream product

• 604-69-3 β-D-glucose pentaacetate 
• 108-98-5 thiophenol 
• 13992-16-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 25878-60-8 D-galactose pentaacetate 
• 439-03-2 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl fluoride 
• 2021-84-3 α-galactosyl fluoride 
• 2936-70-1 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 

Downstream Products

• 909891-53-8 β-D-galactopyranosyl-(1->3)-β-D-glucopyranoside 
• 584-30-5 β-D-galactopyranosyl-(1->3)-α-D-glucopyranoside 

Relevant articles and documents

Glycosynthase with broad substrate specificity-an efficient biocatalyst for the construction of oligosaccharide library

A versatile glycosynthase (TnG-E338A) with strikingly broad substrate scope has been developed from Thermus nonproteolyticus β-glycosidase (TnG) by using site-directed mutagenesis. The practical utility of this biocatalyst has been demonstrated by the facile generation of a small library containing various oligosaccharides and a steroidal glycoside (total 25 compounds) in up to 100 % isolated yield. Moreover, an array of eight gluco-oligosaccharides has been readily synthesized by the enzyme in a one-pot, parallel reaction, which highlights its potential in the combinatorial construction of a carbohydrate library that will assist glycomic and glycotherapeutic research. Significantly, the enzyme provides a means by which glycosynthase technology may be extended to combinatorial chemistry.

Engineering of glucoside acceptors for the regioselective synthesis of β-(1→3)-disaccharides with glycosynthases

Glycosynthase mutants obtained from Thermotoga maritima were able to catalyze the regioselective synthesis of aryl β-d-Galp-(1→3)-β-d-Glcp and aryl β-d-Glcp-(1→3)-β-d-Glcp in high yields (up to 90 %) using aryl β-d-glucosides as acceptors. The need for an aglyconic aryl group was rationalized by molecular modeling calculations, which have emphasized a high stabilizing interaction of this group by stacking with W312 of the enzyme. Unfortunately, the deprotection of the aromatic group of the disaccharides was not possible without partial hydrolysis of the glycosidic bond. The replacement of aryl groups by benzyl ones could offer the opportunity to deprotect the anomeric position under very mild conditions. Assuming that benzyl acceptors could preserve the stabilizing stacking, benzyl β-d-glucoside firstly assayed as acceptor resulted in both poor yields and poor regioselectivity. Thus, we decided to undertake molecular modeling calculations in order to design which suitable substituted benzyl acceptors could be used. This study resulted in the choice of 2-biphenylmethyl β-d-glucopyranoside. This choice was validated experimentally, since the corresponding β-(1→3) disaccharide was obtained in good yields and with a high regioselectivity. At the same time, we have shown that phenyl 1-thio-β-d-glucopyranoside was also an excellent substrate leading to similar results as those obtained with the O-phenyl analogue. The NBS deprotection of the S-phenyl group afforded the corresponding disaccharide quantitatively.