129750-23-8Relevant academic research and scientific papers
RETRACTED ARTICLE: Chemical synthesis and antigenic activity of a phosphatidylinositol mannoside epitope from: Mycobacterium tuberculosis
Zhao, Shi-Yuan,Li, Na,Luo, Wan-Yue,Zhang, Nan-Nan,Zhou, Rong-Ye,Li, Chen-Yu,Wang, Jin
, p. 14067 - 14070 (2020)
Phosphatidylinositol mannosides (PIMs) have been investigated as lipidic antigens for a new subunit tuberculosis vaccine. A non-natural diacylated phosphatidylinositol mannoside (Ac2PIM2) was designed and synthesized by mimicking the natural PIM6 processi
Synthesis of oligosaccharide fragments of mannan from Candida albicans cell wall and their BSA conjugates
Karelin,Tsvetkov,Kogan,Bystricky,Nifantiev
, p. 110 - 121 (2007)
3-Aminopropyl glycosides of α-D-mannopyranosyl-(1→2)-α-D- mannopyranosyl-(1→2)-α-D-mannopyranosyl-(1→2) -α-D-mannopyranose, α-D-mannopyranosyl-(1→3)-α-D- mannopyranosyl-(1→2)-α-D-mannopyranosyl-(1→2) -α-D-mannopyranose, and α-D-mannopyranosyl-(1→2)-[α-D- mannopyranosyl-(1→3)]-α-D-mannopyranosyl-(1→2) -α-D-mannopyranosyl-(1→2)-α-D-mannopyranose were efficiently synthesized starting from ethyl 2-O-acetyl(benzoyl)-3,4,6-tri-O-benzyl-1-thio- α-D-mannopyranoside, ethyl 4,6-di-O-benzyl-2-O-benzoyl-1-thio-α-D- mannopyranoside, ethyl 4,6-di-O-benzyl-2,3-di-O-benzoyl-1-thio-α-D- mannopyranoside, and 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl bromide. The oligosaccharide chains synthesized correspond to the three structural types of side chains of mannan from Candida albicans cell wall. A conjugate of the third pentasaccharide with bovine serum albumin was prepared using the squarate method.
GLYCOMIMETIC COMPOUNDS AND METHODS TO INHIBIT INFECTION BY HIV
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Page/Page column 8, (2011/10/19)
Compounds, compositions and methods are provided for use to inhibit infection by human immunodeficiency virus (HIV). More specifically, the present invention relates to glycomimetic compounds that inhibit HIV infection, and uses thereof.
A highly convergent synthesis of an N-linked glycopeptide presenting the H-type 2 human blood group determinant
Wang, Zhi-Guang,Warren, J. David,Dudkin, Vadim Y.,Zhang, Xufang,Iserloh, Ulrich,Visser, Michael,Eckhardt, Matthias,Seeberger, Peter H.,Danishefsky, Samuel J.
, p. 4954 - 4978 (2007/10/03)
The total synthesis of an H-type blood group determinant in a model biological setting is described. The construct is comprised of a high mannose core structure with projecting lactose spacers, culminating in a two-copy presentation of the H-type blood group determinant itself. Key reactions that were used in this construction include sulfonamidohydroxylation (see 15→18) and benzoate-directed glycosylation via an activated thiophenyl donor (see 34→36). Another key strategic element involved the epimerization of an interior core glucoside to reach the β-mannoside (see 37→38) required in the ring C sugar of the high mannose core.
SmI2/water/amine mediates cleavage of allyl ether protected alcohols: application in carbohydrate synthesis and mechanistic considerations.
Dahlen, Anders,Sundgren, Andreas,Lahmann, Martina,Oscarson, Stefan,Hilmersson, Goeran
, p. 4085 - 4088 (2007/10/03)
[reaction: see text]. SmI2/H2O/amine provides selective cleavage of unsubstituted allyl ethers in good to excellent yields. This method is therefore useful in deprotection of alcohols and carbohydrates.
1,2,5-Ortho esters of D-arabinose as versatile arabinofuranosidic building blocks. Concise synthesis of the tetrasaccharidic cap of the lipoarabinomannan of Mycobacterium tuberculosis
Bamhaoud, Toufiq,Sanchez, Sylvie,Prandi, Jacques
, p. 659 - 660 (2007/10/03)
1,2,5-ortho esters of D-arabinose were found to be ideally suited building blocks for the stereoselective formation of and β arabinofuranosidic linkages after nucleophilic opening of the orthoester with oxygen and sulfur nucleophiles; the tetrasaccharidic cap of the lipoarabinomannan of Mycobacterium tuberculosis was then synthesized in a highly convergent manner.
Synthesis of high-mannose type neoglycolipids: Active targeting of liposomes to macrophages in gene therapy
Dueffels, Arno,Green, Luke G.,Ley, Steven V.,Miller, Andrew D.
, p. 1416 - 1430 (2007/10/03)
The concise synthesis of five biantennary oligomannose neoglycolipids is presented. Employing a strategy based on the principles of reactivity tuning and orthogonal activation, the oligomannose moieties, isolated from the glycoprotein 63 of the parasite L
Chemical synthesis of the W-glycans of gp63, the major surface glycoprotein from Leishmania mexicana amazonemis
Duffels, Arno,Ley, Steven V.
, p. 375 - 378 (2007/10/03)
The chemical synthesis of the conjugated heptasaccharide Man(α1-3)Man(α1-6)[GIc(α1-3)Man(α1-2)Man(α1-2) Man(α1-3)]Manβl-O[CH2]8CO2Me 1 and four closely related biantennary oligomannose type structures derived from the glyc
The synthesis of β-mannopyranosides by intramolecular aglycon delivery: scope and limitations of the exciting methodology
Barresi, Frank,Hindsgaul, Ole
, p. 1447 - 1465 (2007/10/02)
The synthesis of β-mannopyrosides by intramolecular aglycon delivery is shown to proceed with complete stereoselectivity in six separate cases.This strategy has been successfully applied to the synthesis of several disaccharides, including octyl 3,6-di-O-
A stereospecific approach towards the synthesis of 2-deoxy α- and β-glycosides based on a 1,2-ethyl (phenyl) thio group migration
Zuurmond,Van Der Klein,Van Der Marel,Van Boom
, p. 6501 - 6514 (2007/10/02)
Iodonium ion (NIS/TfOH)-assisted glycosylation of a sugar acceptor with properly protected ethyl (phenyl) 2-O-phenoxythiocarbonyl 1-thio-β-D-gluco- or 1-thio-α-D-mannopyranoside donors gives the respective 1,2-trans linked 2'-ethyl (phenyl) thio-2'-deoxy-α-D-manno- or β-D-glucopyranosides.
