83334-22-9

Upstream product

• 6619-09-6 methyl 6-O-tosyl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 23701-87-3 methyl 6-azido-6-deoxy-α-D-glucopyranoside 
• 67-56-1 methanol 
• 866556-24-3 avrainvilloside 
• 23661-33-8 methyl 2,3,4-tri-O-acetyl-6-O-(p-tolylsulfonyl)-α-D-glucopyranoside 
• 1332641-39-0 C₆₃H₆₇NO₉ 
• 52109-81-6 methyl 2,3,4-tri-O-acetyl-6-O-(p-tolylsulfonyl)-α-D-galactopyranoside 
• 52109-83-8 methyl 6-azido-6-deoxy-2,3,4-tri-O-acetyl-α-D-galactopyranoside 
• 34698-19-6 methyl 6-O-tosyl-α-D-galactopyranoside 
• 18908-43-5 methyl 6-azido-6-deoxy-α-D-galactopyranoside 
• 3396-99-4 methyl α-D-galactopyranoside 
• 104652-56-4 3-O-acetyl-1,2-O-isopropylidene-5-O-methylsulfonyl-6-O-(p-nitrobenzoyl)-D-glucofuranose 
• 104652-55-3 3-O-acetyl-1,2-O-isopropylidene-6-O-(p-nitrobenzoyl)-D-glucofuranose 

Downstream Products

• 86462-45-5 methyl 6-(benzyloxycarbonyl)amino-6-deoxy-α-D-glucopyranoside 
• 58994-96-0 Ranimustine 
• 1198571-24-2 methyl 6-(o-nitro)benzamidyl-6-deoxy-α-D-glucopyranoside 
• 1180509-83-4 1-amino-1-deoxy-N-(methyl 6-amino-6-deoxy-α-D-glucopyranosid-6-yl)-5,6-oxomethylidenenojirimycin 
• 1198571-25-3 methyl 6-(o-nitro)benzamidyl-6-deoxy-α-D-galactopyranoside 
• 1202010-98-7 methyl 6-[3-(3-methoxy-4-acetoxyphenyl)propenamido]-6-deoxy-α-D-galactopyranoside 
• 1338809-58-7 methyl 6-deoxy-6-((2S,6S)-6-methoxy-2-(hydroxymethyl)morpholin-4-yl)-α-D-glucopyranoside 
• 628328-88-1 methyl 6-(4-bromomethyl-3-nitrobenzoylamino)-6-deoxy-α-D-glucopyranoside 
• 86462-44-4 methyl 6-benzyloxycarbonylamino-4-chloro-4,6-dideoxy-α-D-galactopyranoside 

Relevant academic research and scientific papers

Synthesis and antibacterial activity of aminodeoxyglucose derivatives against Listeria innocua and Salmonella typhimurium

In this study aminodeoxyglucose derivatives were synthesized and evaluated for their antibacterial activity against two food bacteria, Listeria innocua and Salmonella typhimurium. 6-Amino-6-deoxy-α-Dmethylglucopyranose (GSA-6), 3-amino-3-deoxy-D-glucopyranoside (GSA-3), and β-D-glucopyranosylamine (GSA-1) were synthesized and concurrently tested with commercially available D-glucosamine (GSA-2) for antibacterial activity. Results obtained from this study showed a pronounced antagonist effect due to the position of amino groups of aminoglucose derivatives on the antibacterial activity. GSA-3 was the most active compound. At a concentration of 2 × 10 -4 mol mL -1, it delayed the growth of both bacteria with percentages of inhibition of 29 and 15% for L. innocua and S. typhimurium, respectively. At the same concentration the percentages of inhibition for other aminodeoxyglucoses varied between 5 and 18% and between 2 and 11% for L. innocua and S. typhimurium, respectively. All compounds were characterized by FTIR, 1H NMR, and 13C NMR spectroscopy.

Design, physico-chemical characterization andin vitrobiological activity of organogold(iii) glycoconjugates

To develop new metal-based glycoconjugates as potential anticancer agents, four organometallic gold(iii)-dithiocarbamato glycoconjugates of the type [AuIII(2-Bnpy)(SSC-Inp-GlcN)](PF6) (2-Bnpy: 2-benzylpyridine; Inp: isonipecotic moie

The strategic use of: Para-quinone methides to access synthetically challenging and chemoselective α,α-diarylmethyl N-glycosides from unprotected carbohydrate amines

Reported herein is a practical route to access synthetically challenging and chemoselective α,α-diarylmethyl N-glycosides via Sc(OTf)3-catalyzed 1,6-conjugate addition of amino sugars with para-quinone methides (p-QMs). The reactions proceed smoothly without a base and under mild reaction conditions with a broad substrate scope and moderate to good yields.

An innovative and efficient route to the synthesis of metal-based glycoconjugates: proof-of-concept and potential applications

With a view to developing more efficient strategies to the functionalization of metallodrugs with carbohydrates, we here report on an innovative and efficient synthetic route to generate gold(iii) glycoconjugates in high yields and purity. The method is based on the initial synthesis of the zinc(ii)-dithiocarbamato intermediate [ZnII(SSC-Inp-GlcN)2] (Inp = isonipecotic moiety; GlcN = amino-glucose) followed by the transfer of the glucoseisonipecoticdithiocarbamato ligand to the gold(iii) center via transmetallation reaction between the zinc(ii) intermediate and K[AuIIIBr4] in 1?:?2 stoichiometric ratio, yielding the corresponding glucose-functionalized gold(iii)-dithiocarbamato derivative [AuIIIBr2(SSC-Inp-GlcN)]. No protection/deprotection of the amino-glucose scaffold and no chromatographic purification were needed. The synthetic protocol was optimized for glucose precursors bearing the amino function at either the C2 or the C6 position, and works in the case of both α and β anomers. The application of the synthetic strategy was also successfully extended to other metal ions of biomedical interest, such as gold(i) and platinum(ii), to obtain [AuI(SSC-Inp-GlcN)(PPh3)] and [PtII(SSC-Inp-GlcN)2], respectively. All compounds were fully characterized by elemental analysis, mid- and far-IR, mono- and multidimensional NMR spectroscopy, and, where possible, X-ray crystallography. Results and potential applications are here discussed.

Multicomponent diversity oriented synthesis of multivalent glycomimetics containing hexafluorovaline

The chemoselective introduction of fluorinated moieties into biologically relevant scaffolds is now an established strategy to modulate and to study the properties of molecular leads. In this article we propose, for the first time, the diversity oriented

Cinnamide Derivatives of d-Mannose as Inhibitors of the Bacterial Virulence Factor LecB from Pseudomonas aeruginosa

Pseudomonas aeruginosa is an opportunistic Gram-negative pathogen with high antibiotic resistance. Its lectin LecB was identified as a virulence factor and is relevant in bacterial adhesion and biofilm formation. Inhibition of LecB with carbohydrate-based ligands results in a decrease in toxicity and biofilm formation. We recently discovered two classes of potent drug-like glycomimetic inhibitors, that is, sulfonamides and cinnamides of d-mannose. Here, we describe the chemical synthesis and biochemical evaluation of more than 20 derivatives with increased potency compared to the unsubstituted cinnamide. The structure–activity relationship (SAR) obtained and the extended biophysical characterization allowed the experimental determination of the binding mode of these cinnamides with LecB. The established surface binding mode now allows future rational structure-based drug design. Importantly, all glycomimetics tested showed extended receptor residence times with half-lives in the 5–20 min range, a prerequisite for therapeutic application. Thus, the glycomimetics described here provide an excellent basis for future development of anti-infectives against this multidrug-resistant pathogen.

Cinnamide Derivatives of d-Mannose as Inhibitors of the Bacterial Virulence Factor LecB from Pseudomonas aeruginosa

Pseudomonas aeruginosa is an opportunistic Gram-negative pathogen with high antibiotic resistance. Its lectin LecB was identified as a virulence factor and is relevant in bacterial adhesion and biofilm formation. Inhibition of LecB with carbohydrate-based ligands results in a decrease in toxicity and biofilm formation. We recently discovered two classes of potent drug-like glycomimetic inhibitors, that is, sulfonamides and cinnamides of d-mannose. Here, we describe the chemical synthesis and biochemical evaluation of more than 20 derivatives with increased potency compared to the unsubstituted cinnamide. The structure–activity relationship (SAR) obtained and the extended biophysical characterization allowed the experimental determination of the binding mode of these cinnamides with LecB. The established surface binding mode now allows future rational structure-based drug design. Importantly, all glycomimetics tested showed extended receptor residence times with half-lives in the 5–20 min range, a prerequisite for therapeutic application. Thus, the glycomimetics described here provide an excellent basis for future development of anti-infectives against this multidrug-resistant pathogen.

Quantifying the electronic effects of carbohydrate hydroxy groups by using aminosugar models

Methyl amino-deoxy-glycosides with α- and β-gluco, α-galacto, or α-manno stereochemistry with the amino functionality in each of the four possible non-anomeric positions have been synthesized and their pKa values determined by titration. These

Synthesis and glycosidase inhibitory profiles of functionalised morpholines and oxazepanes

In this work libraries of morpholines and oxazepanes have been prepared via the reductive amination reaction between dialdehydes, derived from carbohydrates, and a range of amines. In this way, functionalised morpholines and oxazepanes have been prepared

Synthesis and α-Glucosidase II inhibitory activity of valienamine pseudodisaccharides relevant to N-glycan biosynthesis

Valienol-derived allylic C-1 bromides have been used as carbaglycosyl donors for α-xylo configured valienamine pseudodisaccharide synthesis. We synthesised valienamine analogues of the Glc(α1→3)Glc and Glc(α1→3)Man disaccharides representing the linkages