3006-58-4

Upstream product

• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 501-53-1 benzyl chloroformate 
• 4710-95-6 D-mannosamine hydrochloride 
• 90-76-6 D-galactosamine 
• 1772-03-8 D-(+)-galactosamine hydrochloride 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 90-76-6 2-deoxy-2-amino glucose 
• 14131-62-5 D-glucosamine hydrochloride 

Downstream Products

• 57089-81-3 methyl 2-benzyloxycarbonylamino-2-deoxy-α/β-D-glucopyranoside 
• 4704-15-8 ((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester 
• 121230-19-1 2-benzyloxycarbonylamino-2-deoxy-4,6-O-ethylidene-α,β-D-glucose 
• 35946-66-8 2-(acetoxymethyl)-5-{[(benzyloxy)carbonyl]amino}tetrahydropyran-3,4,6-triyl triacetate 
• 82264-19-5 1,3,4,6-tetra-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside 
• 5348-99-2 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(benzyloxycarbonyl)amino-α/β-D-glucopyranoside 
• 315229-38-0 ((2S,3R,4S,5R)-2-Benzyloxycarbonylamino-3,4,5,6-tetrahydroxy-hexylamino)-acetic acid methyl ester 
• 315229-51-7 (S)-2-((2S,3R,4S,5R)-2-Benzyloxycarbonylamino-3,4,5,6-tetrahydroxy-hexylamino)-6-tert-butoxycarbonylamino-hexanoic acid methyl ester 
• 138395-73-0 (3aS,4R,5R,6S,6aS)-6-(Acetoxymethyl)-2-oxohexahydro-2H-cyclopenta[d]oxazole-4,5-diyl diacetate 
• 114621-71-5 3,4,6-tri-O-acetylallosamizoline 
• 114673-96-0 (-)-allosamizoline hydrochloride 
• 140183-62-6 1R,2S,3R,5R-3,4-diacetoxy-5-acetoxymethyl-2-benzyloxycarbonylaminocyclopentanol 
• 140183-61-5 2S,3R,4R,5R-2,3-diacetoxy-5-acetoxymethylbenzyloxycarbonylaminocyclopentanone oxime 
• 140183-54-6 2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-D-glucose oxime 

Relevant academic research and scientific papers

Effects of cholesterol on the miscibility of synthetic glucosamine diesters in lipid bilayers and the entrapment of superoxide dismutase into the positively charged liposomes

Methyl-D-glucosamine-3,6-dilauroyl, dimyristoyl, dipalmitoyl or distearoyl esters were synthesized as positively charged lipids. They were incorporated into phosphatidylcholine liposomal membranes and the entrapment of superoxide dismutase (SOD) into the liposomes was attempted. The efficiency of the SOD- entrapment into the positively charged multilamellar vesicles (MLVs), comprising egg yolk phosphatidylcholine and synthetic glucosamine diesters, was enhanced by the addition of cholesterol to the membranes. A differential scanning calorimetric study showed that the miscibility (solubility) of glucosamine diesters in phosphatidylcholine-bilayers increased on the addition of cholesterol to the membranes. Cholesterol assisted in the mixing of phosphatidylcholines with positively charged glucosamine diesters and increased the positive charges on the liposomal membranes. This was confirmed by incremental increases in the zeta-potential of liposomal membranes with an increase in the cholesterol content. Entrapment of SOD thus became more efficient due to the enhanced electrostatic attraction between the positively charged membranes and the negatively charged SOD, and/or the electrostatic repulsive interactions between positively charged membranes; the latter interactions induced a thickening of the water layer in MLVs.

Synthesis and Antigenic Evaluation of Oligosaccharide Mimics of Vi Antigen from Salmonella typhi

Salmonella typhi is responsible for typhoid fever, which is a serious health threat in developing countries. As a virulent factor of Salmonella typhi, the purified Vi polysaccharide (Vi PS) has become an effective vaccine to combat typhoid fever. The chem

Protected N-Acetyl Muramic Acid Probes Improve Bacterial Peptidoglycan Incorporation via Metabolic Labeling

Metabolic glycan probes have emerged as an excellent tool to investigate vital questions in biology. Recently, methodology to incorporate metabolic bacterial glycan probes into the cell wall of a variety of bacterial species has been developed. In order to improve this method, a scalable synthesis of the peptidoglycan precursors is developed here, allowing for access to essential peptidoglycan immunological fragments and cell wall building blocks. The question was asked if masking polar groups of the glycan probe would increase overall incorporation, a common strategy exploited in mammalian glycobiology. Here, we show, through cellular assays, that E. coli do not utilize peracetylated peptidoglycan substrates but do employ methyl esters. The 10-fold improvement of probe utilization indicates that (i) masking the carboxylic acid is favorable for transport and (ii) bacterial esterases are capable of removing the methyl ester for use in peptidoglycan biosynthesis. This investigation advances bacterial cell wall biology, offering a prescription on how to best deliver and utilize bacterial metabolic glycan probes.

Asymmetric Synthesis and Biological Activities of Pactamycin-Inspired Aminocyclopentitols

Pactamycin is a structurally unique aminocyclitol antibiotic with broad-spectrum cell growth inhibitory activity. To explore the bountiful activity of the aminocyclitol core of pactamycin, an efficient, modular, and asymmetric synthesis of aminocyclopentitols resembling the pactamycin pharmacophore has been developed employing a SmI2-mediated imino-pinacol coupling strategy. Two of the compounds exhibited antitumor activity against A375 melanoma cells.

COMPOUNDS AND METHODS TO ENHANCE THE ORAL AVAILABILITY OF GLYCOMIMETICS

Potent E-selecting antagonist compounds are described herein. In certain embodiments, compounds and methods are provided for enhancing the oral availability of glycomimetics. More specifically, in an embodiment, a glyeomimetic is modified to decrease the

AMPHETAMINE PRODRUGS

The present invention relates to amphetamine prodrugs which provide colonic release of amphetamine.

A METHOD FOR OBTAINING CRYSTALLINE LACTO-N-TETRAOSE AND LACTO-N-NEOTETRAOSE PRECURSORS AND MIXTURES THEREOF

A mixture of, preferably a mixture consisting essentially of, an lacto-N-tetraose (LNT) precursor (1) and an lacto-N-neotetraose (LNnT) precursor (2), (formula 1, 2), where R is a group removable by hydrogenolysis and R3 is either a group remov

Chemoenzymatic synthesis of uridine diphosphate-GlcNAc and uridine diphosphate-GalNAc analogs for the preparation of unnatural glycosaminoglycans

Eight N-acetylglucosamine-1-phosphate and N-acetylgalactosamine-1-phosphate analogs have been synthesized chemically and were tested for their recognition by the GlmU uridyltransferase enzyme. Among these, only substrates that have an amide linkage to the C-2 nitrogen were transferred by GlmU to afford their corresponding uridine diphosphate(UDP)-sugar nucleotides. Resin-immobilized GlmU showed comparable activity to nonimmobilized GlmU and provides a more facile final step in the synthesis of an unnatural UDP-donor. The synthesized unnatural UDP-donors were tested for their activity as substrates for glycosyltransferases in the preparation of unnatural glycosaminoglycans in vitro. A subset of these analogs was useful as donors, increasing the synthetic repertoire for these medically important polysaccharides.

Automated solid-phase synthesis of hyaluronan oligosaccharides

Well-defined fragments of hyaluronic acid (HA) have been obtained through a fully automated solid-phase oligosaccharide synthesis. Disaccharide building blocks, featuring a disarmed glucuronic acid donor moiety and a di-tert-butylsilylidene-protected gluc

Hybrid aminoglycoside antibiotics via tsuji palladium-catalyzed allylic deoxygenation

Biosynthetically inspired manipulation of the antibiotic paromomycin led, in six high-yielding steps, to a ring A harboring an R,β-unsaturated 6′- aldehyde and an allylic 3′-methylcarbonate group. Tsuji deoxygenation in the presence of 5 mol % Pd2(dba)3 and Bu3P granted access to a novel series of 3′,4′-dideoxy- 4′,5′-dehydro ring A hybrids. The neomycin-sisomicin hybrid exhibited superior in vitro antibacterial activity to the parent compound neomycin.