24562-43-4

Upstream product

• 67-64-1 acetone 
• 15814-59-2 (2S,3S,4S,5S,6R)-2-methoxy-6-methyltetrahydro-2H-pyran-3,4,5-triol 
• 22932-34-9 methyl 6-deoxy-6-iodo-2,3-O-isopropylidene-α-D-mannopyranoside 
• 112612-45-0 methyl 2,3-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-mannopyranoside 
• 77-76-9 2,2-dimethoxy-propane 
• 85726-76-7 methyl 4-O-benzoyl-2,3-O-isopropylidene-α-D-rhamnopyranoside 
• 51103-66-3 methyl 6-O-(p-tolylsulfonyl)-α-D-mannopyranoside 
• 2592-53-2 methyl 6-deoxy-2,3-O-isopropylidene-α-L-lyxo-hexopyranoside-4-ulose 
• 42214-02-8 methyl 6-deoxy-2,3-O-isopropylidene-α-L-lyxo-hexopyranosid-4-ulose 
• 42214-01-7 methyl 2,3-O-isopropylidene-α-L-rhamnopyranoside 
• 79774-54-2 methyl 4-O-benzoyl-6-deoxy-α-D-glucopyranoside 
• 76116-34-2 methyl chloro-6 desoxy-6 O-isopropylidene-2,3 α-D-mannopyranoside 
• 116-11-0 2-Methoxypropene 
• 5155-43-1 methyl 6-deoxy-α-D-glucopyranoside 

Downstream Products

• 86447-92-9 methyl 4-O-benzyl-6-deoxy-2,3-O-isopropylidene-α-D-mannopyranoside 
• 10515-99-8 methyl 6-deoxy-2,3-O-isopropylidene-4-O-(p-tolylsulfonyl)-α-D-mannopyranoside 
• 135216-53-4 methyl 6-deoxy-2,3-O-isopropylidene-4-O-<(p-nitrophenyl)sulfonyl>-α-D-mannopyranoside 
• 85726-76-7 methyl 4-O-benzoyl-2,3-O-isopropylidene-α-D-rhamnopyranoside 
• 122805-36-1 methyl 4-O-benzoyl-α-D-rhamnopyranoside 
• 756498-00-7 methyl 3-O-allyl-4-O-benzoyl-α-D-rhamnopyranoside 
• 756498-02-9 methyl 4-O-benzoyl-2-O-levulinoyl-α-D-rhamnopyranoside 
• 756498-01-8 methyl 3-O-allyl-4-O-benzoyl-2-O-levulinoyl-α-D-rhamnopyranoside 
• 756498-04-1 2-O-acetyl-3-O-allyl-4-O-benzoyl-αD-rhamnopyranosyl trichloroacetamidate 
• 756498-08-5 3-O-allyl-2,4-di-O-benzoyl-αD-rhamnopyranosyl trichloroacetamidate 
• 756498-06-3 methyl (2,3-di-O-acetyl-4-O-benzoyl-αD-rhamnopyranosyl)-(1->3)-4-O-benzoyl-α-D-rhamnopyranoside 

Relevant academic research and scientific papers

A highly cytotoxic L-rhamnose analogue of the antitumour agent spicamycin

Rhamnospicamycin 2, a rhamnose analogue (containing adenine, a carbohydrate, an amino acid and a fatty acid) of the naturally occurring combinatorial library spicamycin 1, is prepared from L-rhamnose and shown to be highly cytotoxic towards human myeloma cells (IC50 = 120 nM).

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

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.

Bio-inspired synthesis of rare and unnatural carbohydrates and cyclitols through strain driven epimerization

We report a bio-inspired, strain driven epimerization of trans-ketals to cis-ketals through an enolate intermediate. Swern oxidation of a hydroxyl group adjacent to a trans-ketal effects both oxidation and its epimerization to cis-ketal. This novel and general strategy allows inversion of up to three contiguous stereocenters and has been illustrated by the synthesis of several unnatural/rare isomers of carbohydrates/cyclitols from their naturally abundant isomers. This journal is the Partner Organisations 2014.

Probe sialidase substrate specificity using chemoenzymatically synthesized sialosides containing C9-modified sialic acid

A library of α2-3- and α2-6-linked sialyl galactosides containing C9-modified sialic acids was synthesized from C6-modified mannose derivatives using an efficient one-pot three-enzyme system. These sialosides were used in a high-throughput sialidase substrate specificity assay to elucidate the importance of C9-OH in sialidase recognition. The Royal Society of Chemistry 2012.

Synthesis of disaccharides containing 6-Deoxy-α-L-talose as potential heparan sulfate mimetics

A 6-deoxy-α-L-talopyranoside acceptor was readily prepared from methyl α-L-rhamnopyranoside and glycosylated with thiogalactoside donors using NIS/TfOH as the promoter to give good yields of the desired α-linked disaccharide (69-90%). Glycosylation with a 2-azido-2-deoxy-D-glucosyl trichloroacetimidate donor was not completely stereoselective (α:β = 6:1), but the desired α-linked disaccharide could be isolated in good overall yield (60%) following conversion into its corresponding tribenzoate derivative. The disaccharides were designed to mimic the heparan sulfate (HS) disaccharide GlcN(2S,6S)-IdoA(2S). However, the intermediates readily derived from these disaccharides were not stable to the sulfonation/deacylation conditions required for their conversion into the target HS mimetics.

Synthesis of orthogonally protected d-olivoside, 1,3-di-O-acetyl-4-O-benzyl-2,6-dideoxy-d-arabinopyranose, as a C-glycosyl donor

1,3-Di-O-acetyl-4-O-benzyl-2,6-dideoxy-d-arabinopyranose (11) was synthesised from thiophenyl α-d-mannopyranoside (21) in an eight-step sequence. Tosylation of 21 and subsequent reaction with 2,2-dimethoxypropane gave tosylate 22, which upon treatment with lithium aluminium hydride furnished 6-deoxy glycoside 24 and by-product thiophenyl 6-deoxy-2-O-isopropyl-α-d-arabinopyranoside. The X-ray crystal structure of the latter was determined. Benzylation of the 4-hydroxyl group of 24 and subsequent protecting group manipulation gave d-rhamnosyl bromide 29, which on treatment with zinc-copper couple gave the orthogonally protected d-rhamnal 30. Triphenylphosphine hydrogen bromide catalysed addition of acetic acid to 30 furnished the target molecule 11. The scandium(III) triflate promoted reaction of 11 and 2-naphthol gave the corresponding C-glycoside 36 in 86% yield. Crown Copyright

Synthesis and biological evaluation of enantiomeric rhamnose analogues of the antitumour agent spicamycin - Is the mode of action by modification of N-linked glycoproteins?

The synthesis of both enantiomers of dodecyl rhamnospicamycin 2a and 2b, a rhamnose analogue of the naturally occurring combinatorial library spicamycin 1, are derived from L-rhamnose and methyl α-D-mannopyranoside, respectively. The L-(+)-enantiomer 2a c