81704-02-1Relevant articles and documents
Selectively Deoxyfluorinated N-Acetyllactosamine Analogues as 19F NMR Probes to Study Carbohydrate-Galectin Interactions
Kurfi?t, Martin,Dra?ínsky, Martin,?ervenková ??astná, Lucie,Cu?ínová, Petra,Hamala, Vojtěch,Hovorková, Michaela,Bojarová, Pavla,Karban, Jind?ich
supporting information, p. 13040 - 13051 (2021/08/07)
Galectins are widely expressed galactose-binding lectins implied, for example, in immune regulation, metastatic spreading, and pathogen recognition. N-Acetyllactosamine (Galβ1-4GlcNAc, LacNAc) and its oligomeric or glycosylated forms are natural ligands of galectins. To probe substrate specificity and binding mode of galectins, we synthesized a complete series of six mono-deoxyfluorinated analogues of LacNAc, in which each hydroxyl has been selectively replaced by fluorine while the anomeric position has been protected as methyl β-glycoside. Initial evaluation of their binding to human galectin-1 and -3 by ELISA and 19F NMR T2-filter revealed that deoxyfluorination at C3, C4′ and C6′ completely abolished binding to galectin-1 but very weak binding to galectin-3 was still detectable. Moreover, deoxyfluorination of C2′ caused an approximately 8-fold increase in the binding affinity towards galectin-1, whereas binding to galectin-3 was essentially not affected. Lipophilicity measurement revealed that deoxyfluorination at the Gal moiety affects log P very differently compared to deoxyfluorination at the GlcNAc moiety.
Glycosidic linkage, N-acetyl side-chain, and other structural properties of methyl 2-acetamido-2-deoxy-β-d-glucopyranosyl-(1→4)-β-d-mannopyranoside monohydrate and related compounds
Carmichael, Ian,Meredith, Reagan J.,Oliver, Allen G.,Serianni, Anthony S.,Zhang, Wenhui
, p. 287 - 297 (2020/03/17)
The crystal structure of methyl 2-acetamido-2-deoxy-β-d-glycopyranosyl-(1→4)-β-d-mannopyranoside monohydrate, C15H27NO11·H2O, was determined and its structural properties compared to those in a set of mono- and disaccharides bearing N-acetyl side-chains in βGlcNAc aldohexopyranosyl rings. Valence bond angles and torsion angles in these side chains are relatively uniform, but C - N (amide) and C - O (carbonyl) bond lengths depend on the state of hydrogen bonding to the carbonyl O atom and N - H hydrogen. Relative to N-acetyl side chains devoid of hydrogen bonding, those in which the carbonyl O atom serves as a hydrogen-bond acceptor display elongated C - O and shortened C - N bonds. This behavior is reproduced by density functional theory (DFT) calculations, indicating that the relative contributions of amide resonance forms to experimental C - N and C - O bond lengths depend on the solvation state, leading to expectations that activation barriers to amide cis-trans isomerization will depend on the polarity of the environment. DFT calculations also revealed useful predictive information on the dependencies of inter-residue hydrogen bonding and some bond angles in or proximal to β-(1→4) O-glycosidic linkages on linkage torsion angles φ and ψ. Hypersurfaces correlating φ and ψ with the linkage C - O - C bond angle and total energy are sufficiently similar to render the former a proxy of the latter.
Chemoenzymatic Synthesis of Glycoconjugates Mediated by Regioselective Enzymatic Hydrolysis of Acetylated 2-Amino Pyranose Derivatives
Zheng, Changping,Bavaro, Teodora,Tengattini, Sara,Mascherpa, Andrea Gualla,Sollogoub, Matthieu,Zhang, Yongmin,Terreni, Marco
supporting information, p. 3622 - 3631 (2019/06/17)
Highly regioselective deprotection of a series of 2-amino pyranose building blocks was achieved by enzymatic hydrolysis. These monodeprotected intermediates were successfully used in the synthesis of a variety of glycoconjugate derivatives with a core of glucosamine or galactosamine, including neo-glycoproteins and glycosphingolipids. The hydrolysis catalyzed by acetylxylan esterase from Bacillus pumilus (AXE) is suitable for the synthesis of neo-glycoproteins with an N-acetyl glucosamine core. The hydrolysis catalyzed by Candida rugosa lipase (CRL) was successfully applied in the preparation of new sialylated glycolipids starting from glucosamine building blocks protected as phthalimide. This chemoenzymatic approach can be used for the preparation of new glycoconjugate products with anticancer activity.
Regioselective Glycosylation Strategies for the Synthesis of Group Ia and Ib Streptococcus Related Glycans Enable Elucidating Unique Conformations of the Capsular Polysaccharides
Del Bino, Linda,Calloni, Ilaria,Oldrini, Davide,Raso, Maria Michelina,Cuffaro, Rossella,Ardá, Ana,Codée, Jeroen D. C.,Jiménez-Barbero, Jesús,Adamo, Roberto
supporting information, p. 16277 - 16287 (2019/11/14)
Group B Streptococcus serotypes Ia and Ib capsular polysaccharides are key targets for vaccine development. In spite of their immunospecifity these polysaccharides share high structural similarity. Both are composed of the same monosaccharide residues and
Ionic-liquid supported rapid synthesis of an: N -glycan core pentasaccharide on a 10 g scale
Li, Wei,Gao, Yu,Li, Qing,Li, Zhong-Jun
supporting information, p. 4720 - 4727 (2018/07/06)
A new and efficient Ionic Liquid-Supported Oligosaccharide Synthesis (ILSOS) strategy for an N-linked core pentasaccharide on a 10 g scale is reported. This new ILSOS includes a new spacer for an IL support, a new tagging strategy, and fast, efficient and orthogonal removal of the ionic-liquid support, producing the N-linked core pentasaccharide with direct applicability potential in a short time, with high yield and on a large gram scale.
COMPOSITIONS AND METHODS FOR THE TREATMENT OF BACTERIAL INFECTIONS
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, (2018/02/28)
Compositions and methods for the treatment of bacterial infections include compounds containing dimers of cyclic heptapeptides conjugated to one or more monosaccharide or oligosaccharide moieties. In particular, compounds can be used in the treatment of bacterial infections caused by Gram-negative bacteria.
Practical synthesis of latent disarmed S-2-(2-propylthio)benzyl glycosides for interrupted Pummerer reaction mediated glycosylation
Xu, Yang,Zhang, Qian,Xiao, Ying,Wu, Pinru,Chen, Wei,Song, Zejin,Xiao, Xiong,Meng, Lingkui,Zeng, Jing,Wan, Qian
supporting information, p. 2381 - 2384 (2017/05/29)
Practical synthetic methods to latent disarmed S-2-(2-propylthio)benzyl (SPTB) glycosides for interrupted Pummerer reaction mediated glycosylation have been discovered. Among them, both coupling reaction of PTB-Cl with glycosyl thiols and BF3·OEt2 promoted reaction of peracylated glycosides with PTB-SH produced peracylated SPTB glycosides in large scales and with high efficiency.
Glycoconjugate probes containing a core-fucosylated N-glycan trisaccharide for fucose lectin identification and purification
Cai, Deqin,Xun, Chaochao,Tang, Feng,Tian, Xiaobo,Yang, Liyun,Ding, Kan,Li, Wenzhe,Le, Zhiping,Huang, Wei
supporting information, p. 143 - 152 (2017/08/10)
Glyco-PAMAM dendrimers and glyco-agarose beads bearing a core-fucosylated N-glycan trisaccharide GlcNAcβ1,4(Fucα1,6)GlcNAc or a non-fucose disaccharide GlcNAcβ1,4GlcNAc were successfully synthesized and characterized by monosaccharide analysis with HPAEC-PAD technique. These glycoconjugates as fucose lectin probes were applied in fucose-specific lectin detection and purification. The model fucose lectin AAL indicated binding activity with the FITC-labeled PAMAM carrying core-fucose trisaccharide. An affinity chromatography column stuffed with the agarose beads carrying core-fucosylated trisaccharide exhibited a good specificity in purification of AAL than non-fucose disaccharide agarose beads. These novel glycoconjugates bearing the precise and simplified core-fucose N-glycan structure provided a potential application for core-fucose-specific lectin discovery.
Synthetic routes toward the trisaccharide related to the lipopolysaccharide of Burkholderia sp. HKI-402 (B4)
Basu, Nabamita,Mukherjee, Mana Mohan,Ghosh, Rina
, p. 54084 - 54090 (2015/01/16)
A stepwise and a three component one-pot sequential glycosylation reaction has been used for the synthesis of trisaccharide related to the LPS of Burkholderia sp. HKI-402 (B4) employing trichloroacetimidate and thio donors. This journal is
CARBOHYDRATE-MODIFIED GLYCOPROTEINS AND USES THEREOF
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, (2014/10/04)
The present invention provides immunogenic compounds which stimulate immune responses in a subject. The present invention provides compositions comprising an isolated glycoprotein antigen covalently bound at pre-existing carbohydrate residues present on the glycoprotein to a carbohydrate epitope. The present invention also provides a method to induce an immune response in a subject comprising administering the compounds of the invention. The present invention further provides methods of making the compounds of the invention and methods of using the compounds of the invention to stimulate immune responses to infectious disease agents and tumors.
