42793-97-5

Upstream product

• 67-56-1 methanol 
• 10323-20-3 D-Arabinose 
• 98-88-4 benzoyl chloride 
• 3795-68-4 methyl α-L-arabinofuranoside 
• 87-72-9 L-(+)-arabinose 
• 38029-69-5 α-L-arabinofuranoside 
• 22796-65-2 p-nitrophenyl α-L-arabinofuranoside 
• 5328-37-0 L-arabinose 
• 1824-96-0 Methyl α-lyxofuranoside 
• 79083-42-4 methyl D-arabinofuranoside 
• 28697-53-2 D-arabinopyranose 
• 532-20-7 D-arabinofuranose 
• 25545-03-3 β-D-arabinofuranose 
• 56607-40-0 methyl D-arabinofuranoside 

Downstream Products

• 502761-66-2 C₁₃H₁₆O₆C₁₄H₈O₂ 
• 1431370-34-1 3,5-di-O-benzoyl-β-D-arabinofuranoside-prop-2-ynyl-1,2-orthobenzoate 
• 1431370-38-5 (pent-4-enyl) 2,3,5-tri-O-benzoyl-α-D-arabinofuranoside 
• 103702-71-2 benzyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranoside 
• 1431370-40-9 benzyl N-(benzyloxycarbonyl)-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-L-serinate 
• 1431370-42-1 methyl 2,3,6-tri-O-benzyl-4-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-α-D-glucopyranoside 
• 1431370-43-2 pent-4-enyl 2,3,4-tri-O-benzyl-6-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-α-D-mannopyranoside 
• 1431370-45-4 propargyl 3,5-di-O-benzyl-2-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside 
• 1431370-35-2 3,5-di-O-benzyl-β-D-arabinofuranoside (prop-2-yn-1-yl)-1,2-orthobenzoate 
• 1431370-60-3 pent-4-enyl 2,3-di-O-benzyl-5-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside 
• 1431370-61-4 pent-4-enyl 2,3-di-O-benzyl-5-O-(α-D-arabinofuranosyl)-α-D-arabinofuranoside 
• 1431370-62-5 pent-4-enyl 2,3-di-O-benzyl-5-O-(2-O-benzyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside 
• 1449126-02-6 C₁₅H₁₆O₆ 
• 1431370-77-2 C₄₁H₆₄O₁₀Si₂ 

Relevant academic research and scientific papers

Total Synthesis of a Partial Structure from Arabinogalactan and Its Application for Allergy Prevention

Arabinogalactan, a microheterogeneous polysaccharide occurring in plants, is known for its allergy-protective activity, which could potentially be used for preventive allergy treatment. New treatment options are highly desirable, especially in a preventive manner, due to the constant rise of atopic diseases worldwide. The structural origin of the allergy-protective activity of arabinogalactan is, however, still unclear and isolation of the polysaccharide is not feasible for pharmaceutical applications due to a variation of the activity of the natural product and contaminations with endotoxins. Therefore, a pentasaccharide partial structure was selected for total synthesis and subsequently coupled to a carrier protein to form a neoglycoconjugate. The allergy-protective activity of arabinogalactan could be reproduced with the partial structure in subsequent in vivo experiments. This is the first example of a successful simplification of arabinogalactan with a single partial structure while retaining its allergy-preventive potential.

Synthesis of Arabinoxylan Oligosaccharides by Preactivation-Based Iterative Glycosylations

A concise synthetic strategy has been developed for assembling densely substituted arabinoxylan oligosaccharides, which are valuable substrates for characterizing hemicellulose-degrading enzymes. The xylan backbone has been prepared by an iterative preact

Active Site Mapping of Xylan-Deconstructing Enzymes with Arabinoxylan Oligosaccharides Produced by Automated Glycan Assembly

Xylan-degrading enzymes are crucial for the deconstruction of hemicellulosic biomass, making the hydrolysis products available for various industrial applications such as the production of biofuel. To determine the substrate specificities of these enzymes, we prepared a collection of complex xylan oligosaccharides by automated glycan assembly. Seven differentially protected building blocks provided the basis for the modular assembly of 2-substituted, 3-substituted, and 2-/3-substituted arabino- and glucuronoxylan oligosaccharides. Elongation of the xylan backbone relied on iterative additions of C4-fluorenylmethoxylcarbonyl (Fmoc) protected xylose building blocks to a linker-functionalized resin. Arabinofuranose and glucuronic acid residues have been selectively attached to the backbone using fully orthogonal 2-(methyl)naphthyl (Nap) and 2-(azidomethyl)benzoyl (Azmb) protecting groups at the C2 and C3 hydroxyls of the xylose building blocks. The arabinoxylan oligosaccharides are excellent tools to map the active site of glycosyl hydrolases involved in xylan deconstruction. The substrate specificities of several xylanases and arabinofuranosidases were determined by analyzing the digestion products after incubation of the oligosaccharides with glycosyl hydrolases.

Preparation of the tri-arabino di-mycolate fragment of mycobacterial arabinogalactan from defined synthetic mycolic acids

An efficient synthetic approach to tri-arabino di-mycolates, using structurally defined synthetic α-, keto and methoxy mycolic acids is described.

Synthesis of β-1,4-Linked Galactan Side-Chains of Rhamnogalacturonan I

The synthesis of linear- and (1→6)-branched β-(1→4)-d-galactans, side-chains of the pectic polysaccharide rhamnogalacturonan I is described. The strategy relies on iterative couplings of n-pentenyl disaccharides followed by a late stage glycosylation of a common hexasaccharide core. Reaction with a covalent linker and immobilization on N-hydroxysuccinimide (NHS)-modified glass surfaces allows the generation of carbohydrate microarrays. The glycan arrays enable the study of protein–carbohydrate interactions in a high-throughput fashion, demonstrated herein with binding studies of mAbs and a CBM.

Araf51 with improved transglycosylation activities: One engineered biocatalyst for one specific acceptor

A random mutagenesis of the arabinofuranosyl hydrolase Araf51 has been run in order to have access to efficient biocatalysts for the synthesis of alkyl arabinofuranosides. The mutants were selected on their ability to catalyze the transglycosylation reaction of p-nitrophenyl α-l-arabinofuranoside (pNP-Araf) used as a donor and various aliphatic alcohols as acceptors. This screening strategy underlined 5 interesting clones, each one corresponding to one acceptor. They appeared to be much more efficient in the transglycosylation reaction compared to the wild type enzyme whereas no self-condensation or hydrolysis products could be detected. Moreover, the high specificity of the mutants toward the alcohols for which they have been selected validates the screening process. Sequence analysis of the mutated enzymes revealed that, despite their location far from the active site, the mutations affect significantly the kinetics properties as well as the substrate affinity of these mutants toward the alcohol acceptors in the transglycosylation reaction.

Araf51 with improved transglycosylation activities: One engineered biocatalyst for one specific acceptor

A random mutagenesis of the arabinofuranosyl hydrolase Araf51 has been run in order to have access to efficient biocatalysts for the synthesis of alkyl arabinofuranosides. The mutants were selected on their ability to catalyze the transglycosylation reaction of p-nitrophenyl α-l-arabinofuranoside (pNP-Araf) used as a donor and various aliphatic alcohols as acceptors. This screening strategy underlined 5 interesting clones, each one corresponding to one acceptor. They appeared to be much more efficient in the transglycosylation reaction compared to the wild type enzyme whereas no self-condensation or hydrolysis products could be detected. Moreover, the high specificity of the mutants toward the alcohols for which they have been selected validates the screening process. Sequence analysis of the mutated enzymes revealed that, despite their location far from the active site, the mutations affect significantly the kinetics properties as well as the substrate affinity of these mutants toward the alcohol acceptors in the transglycosylation reaction.

Automated solid phase synthesis of oligoarabinofuranosides

Automated solid phase synthesis enables rapid access to the linear and branched arabinofuranoside oligosaccharides. A simple purification step is sufficient to provide the conjugation ready oligosaccharides in good yield.

Chiral pyrroline-based Ugi-three-component reactions are under kinetic control

Although it is often assumed that the stereochemistry in Ugi multicomponent reactions is determined in the final Mumm rearrangement step, experimental and computational evidence that Ugi reactions on hydroxylated pyrrolines proceed under kinetic control is reported. The stereochemistry of the reaction is established with the addition of the isocyanide to the intermediate iminium ion, whose conformation is determined by its substitution pattern.

Facile synthesis of β- And α-arabinofuranosides and application to cell wall motifs of M. tuberculosis

Propargyl 1,2-orthoesters of arabinose are exploited for the synthesis of 1,2-trans furanosides; easily accessible 1,2-trans ribofuranosides are converted to challenging 1,2-cis-arabinofuranosides by oxidoreduction. Utility of these protocols was demonstrated by the successful synthesis of major structural motifs present in the cell surface of Mycobacterium tuberculosis. Key furanosylations were carried out under gold-catalyzed glycosidation conditions.