204918-48-9Relevant academic research and scientific papers
A stereoselective synthesis method for β-D-arabinofuran glycoside bonds
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, (2022/01/08)
The present invention belongs to the field of natural oligosaccharide chain synthesis technology, specifically relates to a β-D- arabinofuran glycoside bond stereoselective synthesis method, the present invention to 2- O- benzyl-3,5-O- xylene -D- arabfura
Chemoenzymatic synthesis of arabinomannan (AM) glycoconjugates as potential vaccines for tuberculosis
Li, Zhihao,Bavaro, Teodora,Tengattini, Sara,Bernardini, Roberta,Mattei, Maurizio,Annunziata, Francesca,Cole, Richard B.,Zheng, Changping,Sollogoub, Matthieu,Tamborini, Lucia,Terreni, Marco,Zhang, Yongmin
supporting information, (2020/07/27)
Mycobacteria infection resulting in tuberculosis (TB) is one of the top ten leading causes of death worldwide in 2018, and lipoarabinomannan (LAM) has been confirmed to be the most important antigenic polysaccharide on the TB cell surface. In this study, a convenient synthetic method has been developed for synthesizing three branched oligosaccharides derived from LAM, in which a core building block was prepared by enzymatic hydrolysis in flow chemistry with excellent yield. After several steps of glycosylations, the obtained oligosaccharides were conjugated with recombinant human serum albumin (rHSA) and the ex-vivo ELISA tests were performed using serum obtained from several TB-infected patients, in order to evaluate the affinity of the glycoconjugate products for the human LAM-antibodies. The evaluation results are positive, especially compound 21 that exhibited excellent activity which could be considered as a lead compound for the future development of a new glycoconjugated vaccine against TB.
Preparation of the tri-arabino di-mycolate fragment of mycobacterial arabinogalactan from defined synthetic mycolic acids
Mohammed, Mohsin O.,Al Dulayymi, Juma'a R.,Baird, Mark S.
supporting information, p. 36 - 42 (2016/11/25)
An efficient synthetic approach to tri-arabino di-mycolates, using structurally defined synthetic α-, keto and methoxy mycolic acids is described.
Arabinofuranosyl oligosaccharides from mycobacteria: Synthesis and effect of glycosylation on ring conformation and hydroxymethyl group rotamer populations
D'Souza, Francis W.,Ayers, Joseph D.,McCarren, Patrick R.,Lowary, Todd L.
, p. 1251 - 1260 (2007/10/03)
A series of αD-arabinofuranosyl oligosaccharides (2-8) that are fragments of the arabinan portions of two polysaccharides present in the cell wall of Mycobacterium tuberculosis have been synthesized. Preparation of the oligosaccharides involved the sequen
Synthetic arabinofuranosyl oligosaccharides as mycobacterial arabinosyltransferase substrates
Ayers, Joseph D.,Lowary, Todd L.,Morehouse, Caroline B.,Besra, Gurdyal S.
, p. 437 - 442 (2007/10/03)
A series of arabinofuranosyl oligosaccharides found as constituent parts of the polysaccharide portion of the cell wall of Mycobacterium tuberculosis have been chemically synthesized. Screening of these oligosaccharidss as substrates for arabinosyltransferases present in mycobacterial membrane preparations suggests that modified oligosaccharide analogs as small as disaccharides may be inhibitors of glycan biosynthesis. Such inhibitors would be of potential utility as lead compounds in the identification of new drugs for the treatment of mycobacterial infections.
Conversion of pyranose glycals to furanose derivatives: A new route to oligofuranosides
D'Souza, Francis W.,Cheshev, Pavel E.,Ayers, Joseph D.,Lowary, Todd L.
, p. 9037 - 9044 (2007/10/03)
Acetylated pyranose glycals have been converted through a convenient three-step process into protected furanose reducing sugars. Ozonolysis of 2,3,5-tri-O-acetyl-glucal or 2,3,5-tri-O-acetylgalactal, followed by treatment with dimethyl sulfide and then hydrolysis gave respectively protected arabinofuranose (6) and lyxofuranose (7) derivatives. Conversion of these hemiacetals to oligosaccharides was explored using a number of methods. Activation of 6 or 7 in situ afforded glycosides in modest yield and stereoselectivity. Glycosylation of tetraacetates 16 and 18, obtained from 6 and 7, gave similar results. However, thioglycosides 17 and 19, also derived from 6 and 7, were found to be effective glycosyl donors, producing products in good to excellent yields and with high stereoselectivities. The method was also used to synthesize a disaccharide in which one residue contained uniform 13C enrichment.
