4132-46-1

Upstream product

• 2280-44-6 D-Glucose 
• 62-53-3 aniline 
• 133-89-1 UDP-glucose 
• 492-61-5 β-D-glucose 
• 622-37-7 Phenyl azide 

Downstream Products

• 42891-46-3 (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(phenylamino)tetrahydro-2H-pyran-3,4,5-triyl triacetate 

Relevant academic research and scientific papers

Synthesis and antiproliferative activity of selenoindirubins and selenoindirubin-N-glycosides

Selenoindirubins and selenoindirubin-N-glycosides were prepared by the reaction of isatins and isatin-N-glycosides with 3-acetoxy-benzo[b]selenophene, respectively. While selenoindirubin-N-glycosides have not been reported before, three non-glycosylated s

Direct synthesis of β-N-glycosides by the reductive glycosylation of azides with protected and native carbohydrate donors

A simple and straightforward method for the stereocontrolled synthesis of β-linked N-glycosides uses alkyl and aryl azides as the nitrogen source. The N-glycosides are formed in high yields and with high βselectivities (typically >70 % yield, >15:1 β:α selectivity). This approach is also amenable to the synthesis of N-glycosylated amino acids and peptides (see example, Fmoc=9-fluorenylmethoxycarbonyl). Copyright

Probing the aglycon promiscuity of an engineered glycosyltransferase

(Figure Presented) A sweet library: Two variants (wild-type (WT) and a triple mutant) of glycosyltransferase (GT) OleD have been shown to catalyze glycosylation of over 70 substrates, formation of O-, S- and N-glycosidic bonds, and iterative glycosylation (see scheme). Identified substrates include nucleophiles not previously known to act in GT reactions and span numerous natural product and therapeutic drug classes.

One-pot stereoselective synthesis of β-N-aryl-glycosides by N-glycosylation of aromatic amines: application to the synthesis of tumor-associated carbohydrate antigen building blocks

We studied the stereoselective synthesis of several β-N-aryl-glycosides by glycosylation of aromatic primary amines using unprotected carbohydrates in aqueous solution. This was the first report showing an efficient method for the synthesis with one step of β-N-glycosyl-para-amino-phenyl alanine building blocks for the tumor-associated carbohydrate antigen (TACA) glycopeptides synthesis. Analysis of products by 1H and 13C NMR indicated that the Amadori rearrangement had not occurred after formation of the stereoselective β-N-glycoside bond (natural N-glycoprotein linkage). The study of the chemical and enzymatic stability in aqueous media of β-N-aryl-glycosides synthesized was also investigated. For the first time we have shown that the N-glycosidic bond was relatively stable at pH near to 7 and more stable than the O-glycosidic bond to enzymatic hydrolysis. This higher enzymatic and chemical stability of the N-glycosidic bond is essential to envisage further development of stable TACA building blocks.

N.M.R. STUDIES OF D-RIBOSYLAMINES IN SOLUTION: DERIVATIVES OF PRIMARY AMINES

N.m.r. spectroscopy (1H, 13C) has been used to show that primary amines condense with D-ribose to give mainly D-ribopyranosylamines in which the α anomer in the 1C4 conformation preponderates; the β anomer assumes mainly the 4C1 conformation.Thus, it is possible to deduce the structures of N-phenyl-D-ribosylamines and to correlate some of the literature data.For 2,3-O-isopropylidene-D-ribofuranosylamine derivatives, the Δδ values for 13C-n.m.r. signals of the isopropylidene methyl groups can be used to establish the anomeric configuration.