63167-69-1

Usage

InChI:InChI=1/C7H15NO4S.Na/c9-13(10,11)7-1-2-8-3-5-12-6-4-8;/h1-7H2,(H,9,10,11);

Upstream product

• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 112612-45-0 methyl 2,3-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-mannopyranoside 
• 77-76-9 2,2-dimethoxy-propane 
• 13035-60-4 methyl 2,3:4,6-di-O-isopropylidene-α-D-mannopyranoside 
• 67-64-1 acetone 
• 530-26-7 D-Mannose 

Downstream Products

• 74334-90-0 methyl 2,3-O-isopropylidene-6-O-trityl-α-D-mannopyranoside 
• 13035-60-4 methyl 2,3:4,6-di-O-isopropylidene-α-D-mannopyranoside 
• 87591-39-7 Methyl-4-O-acetyl-2,3-O-isopropyliden-6-O-trityl-α-D-mannopyranosid 
• 84553-74-2 methyl 4,6-di-O-benzyl-2,3-O-isopropylidene-α-D-mannopyranoside 
• 79635-91-9 methyl 6-O-benzoyl-4-O-p-methoxybenzoyl-α-D-mannopyranoside 
• 79635-94-2 methyl 4-O-benzoyl-2,3-O-isopropylidene-6-O-p-methoxybenzoyl-α-D-mannopyranoside 
• 71204-54-1 methyl 4,6-di-O-benzoyl-2,3-O-isopropylidene-α-D-mannopyranoside 
• 79635-88-4 methyl 2,3-O-isopropylidene-4,6-di-O-p-nitrobenzoyl-α-D-mannopyranoside 
• 82185-79-3 methyl 4-O-benzyl-2,3-O-isopropylidene-α-D-mannopyranoside 
• 82185-80-6 methyl 2,3-O-isopropylidene-6-O-benzyl-α-D-mannopyranoside 
• 84562-00-5 (3aS,4S,6R,7R,7aS)-7-(4-Bromo-benzyloxy)-6-(4-bromo-benzyloxymethyl)-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran 
• 10515-99-8 methyl 6-deoxy-2,3-O-isopropylidene-4-O-(p-tolylsulfonyl)-α-D-mannopyranoside 
• 88713-96-6 methyl 4,6-di-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-α-D-mannopyranoside 
• 131089-35-5 methyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside 

Relevant academic research and scientific papers

USE OF FUCOSYLATION INHIBITOR FOR PRODUCING AFUCOSYLATED ANTIBODY

The present invention provides inhibitors of fucosylation during protein expression from mammalian cells. The inhibitors are derived from rhamnose and act by inhibition of GDP-mannose 4,6-dehydratase (GMD). The invention further provides methods of making

Preparation method of hydroxyl pyrone compound

The invention provides a preparation method of 3-hydroxyl-2-(hydroxymethyl)-4H-pyran-4-one, and belongs to the field of pharmaceutical and chemical industry. The method comprises the following steps:reacting ethoxy pyran and ketone compounds with p-toluen

Synthetic glycoconjugates characterize the fine specificity of: Brucella A and M monoclonal antibodies

The dominant cell wall antigen of Brucella bacteria is the O-polysaccharide component of the smooth lipopolysaccharide. Infection by various Brucella biovars causes abortions and infertility in a wide range of domestic and wild animals and debilitating disease in humans. Diagnosis relies on the detection of antibodies to the A and M antigens expressed in the O-polysaccharide. This molecule is a homopolymer of the rare monosaccharide, 4-formamido-4,6-dideoxy-d-mannopyranose (Rha4NFo). The A epitope is created by a uniform α1,2 linked internal polymeric sequence capped by a distinct tetrasaccharide sequence defining the M antigen. Unique oligosaccharides only available by chemical synthesis and conjugated via reducing and non-reducing residues to bovine serum albumin have revealed the structural basis of the fine specificity that allows the discrimination of these closely related A and M epitopes. All three M specific monoclonal antibodies (mAbs) are inferred to possess groove type binding sites open at each end, and recognize an α1,3 linked Rha4NFo disaccharide as a part of a trisaccharide epitope, which in two mAbs includes the terminal Rha4NFo residue. The binding site of one of these antibodies is sufficiently large to engage up to six Rha4NFo residues and involves weak recognition of α1,2 linked Rha4NFo residues. The third mAb binds an internal trisaccharide epitope of the M tetrasaccharide. Two A specific mAbs also possess groove type binding sites that accommodate six and four α1,2 linked Rha4NFo residues.

Mechanistic investigation of the radical S -adenosyl- L -methionine enzyme DesII using fluorinated analogues

DesII is a radical S-adenosyl-l-methionine (SAM) enzyme that can act as a deaminase or a dehydrogenase depending on the nature of its TDP-sugar substrate. Previous work has implicated a substrate-derived, C3-centered α-hydroxyalkyl radical as a key interm

Molecular recognition of brucella A and M antigens dissected by synthetic oligosaccharide glycoconjugates leads to a disaccharide diagnostic for brucellosis

The cell wall O-polysaccharides of pathogenic Brucella species are homopolymers of the rare sugar 4,6-dideoxy-4-formamido- α-d-mannopyranose. Despite the apparent simplicity of the polysaccharide it appears to be a "block copolymer" composed of A and M polysaccharide sequences expressed as a single molecule. The simultaneous presence of both in the cell wall has complicated the understanding of the molecular recognition of these antigens by antibodies present in the serum of infected animals and humans and by monoclonal antibodies. Since presumptive diagnosis of brucellosis, a serious disease in domestic livestock, wild animals, and humans, is based on detection of these antibodies it is important to separate the two antigenic epitopes, one of which is also found in other bacteria. Chemical synthesis provides the only means to achieve this outcome. A series of six oligosaccharides from di to hexasaccharides 1-6 were synthesized and conjugated to proteins to provide glycoconjugate antigens and conjugate vaccines. These chemically defined antigens identified the M antigenic determinant and provided a structural basis for understanding the fine specificity of monoclonal and polyclonal antibodies that bind the M antigen. This resulted in the discovery of a disaccharide that shows considerable potential as an unambiguous diagnostic antigen for detecting brucellosis in humans and animals and two hexasaccharide conjugate vaccine candidates that produce high levels of O-polysaccharide specific antibodies in mice.

Gold nanoparticles decorated with mannose-6-phosphate analogues

Herein, the preparation of neoglycoconjugates bearing mannose-6-phosphate analogues is described by: (a) synthesis of a cyclic sulfate precursor to access the carbohydrate head-group by nucleophilic displacement with an appropriate nucleophile; (b) introduction of spacers on the mannose-6-phosphate analogues via Huisgen's cycloaddition, the Julia reaction, or the thiol-ene reaction under ultrasound activation. With the resulting compounds in hand, gold nanoparticles could be functionalized with various carbohydrate derivatives (glycoconjugates) and then tested for angiogenic activity. It was observed that the length and flexibility of the spacer separating the sugar analogue from the nanoparticle have little influence on the biological response. One particular nanoparticle system substantially inhibits blood vessel growth in contrast to activation by the corresponding monomeric glycoconjugate, thereby demonstrating the importance of multivalency in angiogenic activity.

Hydroxy group acidities of partially protected glycopyranosides

A comprehensive acidity study of carbohydrate hydroxy groups has been carried out. Relative acidities (Ke) were determined spectrophotometrically for partially methylated methyl α-D- glycopyranosides. Apparently, the acidity is strongly affected by intramolecular hydrogen bonding as well as stereochemistry and solvation. By comparison with pKe and pKa values of aliphatic alcohols and polyols the first estimation of the pKa values for partially protected glycopyranosides was obtained. These findings contribute to the understanding of the relative reactivities of carbohydrate hydroxy groups.

Synthesis, gp120 binding and anti-HIV activity of fatty acid esters of 1,1-linked disaccharides

Inspired by the anti-human immunodeficiency virus (HIV) activity of analogues of β-galactosylceramide (GalCer), a set of mono- and di-saccharide fatty acid esters were designed as GalCer mimetics and their binding to the V3 loop peptide of HIV-1 and anti-

Palladium-catalyzed intramolecular C-O bond formation: An approach to the synthesis of chiral benzodioxocines

Palladium-catalyzed intramolecular aryl etherification using bulky binaphthylphosphane or bis(diphenylphosphanyl)ferrocene ligands is shown to be a convenient method for the synthesis of eight-membered oxygen heterocycles. Application of this methodology to a sugar derivative led to the synthesis of chiral benzodioxocine. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.