- Exploring the Biochemical Foundations of a Successful GLUT1-Targeting Strategy to BNCT: Chemical Synthesis and in Vitro Evaluation of the Entire Positional Isomer Library of ortho-Carboranylmethyl-Bearing Glucoconjugates
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Boron neutron capture therapy (BNCT) is a noninvasive binary therapeutic modality applicable to the treatment of cancers. While BNCT offers a tumor-targeting selectivity that is difficult to match by other means, the last obstacles preventing the full har
- Matovi?, Jelena,J?rvinen, Juulia,Sokka, Iris K.,Imlimthan, Surachet,Raitanen, Jan-Erik,Montaser, Ahmed,Maaheimo, Hannu,Huttunen, Kristiina M.,Per?niemi, Sirpa,Airaksinen, Anu J.,Sarparanta, Mirkka,Johansson, Mikael P.,Rautio, Jarkko,Ekholm, Filip S.
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p. 285 - 304
(2020/12/21)
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- Simple and mild stereoselective O-glycosidation using 1,2-anhydrosugars under neutral conditions
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The ring opening of α-D-1,2-anhydrohexapyranoses with phenols proceeded smoothly in ethyl acetate (neutral conditions) in the absence of metal ion catalysts or additives to stereoselectively furnish 1,2-cis-α-aryl glycosides as the major product and 1,2-t
- Somasundaram, Devaraj,Balasubramanain, Kalpattu K.,Shanmugasundaram, Bhagavathy
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supporting information
p. 764 - 767
(2019/02/16)
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- An Unexpected FeCl 3/C-Catalyzed β-Stereoselective Glycosylation in the Presence of the C(2)-Benzyl Group
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An efficient and completely β-stereoselective glycosylation that did not rely on neighboring group participation is described using 2-20 molpercent FeCl 3 /C as the catalyst and benzylated propargyl glycosides as the donors to reach yields up to 96percent under mild condition. With an octatomic-ring intermediate at the α-face of FeCl 3 /C with alkyne of propargyl glycosides, a panel of aglycones comprising aliphatic, alicyclic, unsaturated alcohols, halogenated alcohols, and phenols with different substitution were examined successfully for the exclusive β-stereoselective glycosylation reaction.
- Guo, Hong,Li, Juan,Si, Wenshuai,Tang, Jie,Tang, Tianjun,Wang, Zhongfu,Yang, Guofang,Zhang, Jianbo
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p. 2984 - 3000
(2019/07/22)
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- Ionic liquids as phase transfer catalysts: Enhancing the biphasic extractive epoxidation reaction for the selective synthesis of β-O-glycosides
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Ionic liquids promoted the direct epoxidation of glycals acting as PTC. 1,2-anhydrosugars were prepared by the oxidation of glycals under biphasic conditions with dimethydioxirane generated in situ from oxone/acetone and amphiphilic IL's as catalysts. β-O
- Santiago, Cintia C.,Lafuente, Leticia,Bravo, Rodolfo,Díaz, Gisela,Ponzinibbio, Agustín
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p. 3739 - 3742
(2017/09/02)
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- Glycosyl dithiocarbamates: β-selective couplings without auxiliary groups
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In this article, we evaluate glycosyl dithiocarbamates (DTCs) with unprotected C2 hydroxyls as donors in β-linked oligosaccharide synthesis. We report a mild, one-pot conversion of glycals into β-glycosyl DTCs via DMDO oxidation with subsequent ring opening by DTC salts, which can be generated in situ from secondary amines and CS2. Glycosyl DTCs are readily activated with Cu(I) or Cu(II) triflate at low temperatures and are amenable to reiterative synthesis strategies, as demonstrated by the efficient construction of a tri-β-1,6-linked tetrasaccharide. Glycosyl DTC couplings are highly β-selective despite the absence of a preexisting C2 auxiliary group. We provide evidence that the directing effect is mediated by the C2 hydroxyl itself via the putative formation of a cis-fused bicyclic intermediate.
- Padungros, Panuwat,Alberch, Laura,Wei, Alexander
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p. 2611 - 2624
(2014/04/17)
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- Access to new carbohydrate-functionalized polylactides via organocatalyzed ring-opening polymerization
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The 4-dimethylaminopyridine (DMAP) catalyzed ring-opening polymerization of lactide using various carbohydrate initiators has been assessed for the functionalization of polylactide. Selectively protected glucose derivatives bearing a free primary alcohol (Glc-1r) and a free secondary alcohol (Glc-2r), glucose and cyclodextrin diol derivatives (Glc-diol and CD-diol), methyl-α-d-glucopyranoside (Glc-Me) and native β-cyclodextrin (CD) were used as initiators. According to the solubility of the carbohydrate derivative, the polymerizations were conducted in chlorinated solvents and in the bulk. Relatively narrow distributions are obtained in high yields in the absence of side reactions, affording a 100% functionalization efficiency. The catalytic synthesis of new carbohydrate link-functionalized polylactides and carbohydrate core star polylactides is reported.
- Miao, Yong,Rousseau, Cyril,Mortreux, André,Martin, Patrick,Zinck, Philippe
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experimental part
p. 5018 - 5026
(2012/06/29)
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- Multivalent glyconanoparticles with enhanced affinity to the anti-viral lectin Cyanovirin-N
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Low-mannose (LM) structures were coupled to gold nanoparticles (Au NPs) to amplify the affinity of LMs with Cyanovirin-N (CV-N) lectins and to study the structures of CV-N variants CVNQ50C and CVNMutDB. The Royal Society of Chemistry
- Wang, Xin,Matei, Elena,Deng, Lingquan,Ramstroem, Olof,Gronenborn, Angela M.,Yan, Mingdi
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p. 8620 - 8622
(2011/09/19)
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- The Glc2Man2-fragment of the N-glycan precursor - A novel ligand for the glycan-binding protein malectin?
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The Glcα(1→3)Glcα(1→3)Manα(1→2)Man tetrasaccharide (Glc2Man2-fragment), a substructure of the natural N-glycan precursor, was synthesized. The interaction of this fragment with the protein malectin, a carbohydrate binding protein localized in the endoplasmatic reticulum, was investigated by 1H15N HSQC experiments and isothermal calorimetry. The chemical shift perturbations of nuclei in the protein's backbone caused by the binding of the Glc 2Man2-fragment to malectin suggest a binding mode like the known ligand nigerose. The Royal Society of Chemistry 2010.
- Mueller, Lisa N.,Muhle-Goll, Claudia,Biskup, Moritz B.
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supporting information; experimental part
p. 3294 - 3299
(2010/08/21)
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- Sonication-assisted oligomannoside synthesis
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We have investigated the use of sonication for the synthesis of oligomannosides. A convenient sonication- mediated glycosylation protocol that is applicable to traditional glycosylation methods has been developed. This protocol can be applicable for activ
- Tanifum, Christabel T.,Chang, Cheng-Wei T.
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experimental part
p. 634 - 644
(2009/06/28)
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- Orthoester-based strategy for efficient synthesis of the virulent antigenic-1,2-linked oligomannans of Candida albicans
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Orthobenzoates of glucose and mannose provide donor and acceptor partners to produce a disaccharide bearing a benzoyl group at the site where gluco to manno conversion is required, the inverted center being ready to function, iteratively, as the next acce
- Mathew, Felix,Mach, Mateusz,Hazen, Kevin C.,Fraser-Reid, Bert
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p. 1319 - 1322
(2007/10/03)
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- Comparing n-pentenyl orthoesters and n-pentenyl glycosides as alternative glycosyl donors
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As is well known, cyclic 1,2-glycosyl orthoesters undergo ready acid catalyzed rearrangement to 2-O-acyl glycosides in which the alkoxy group is transferred from the orthoester to the anomeric center in a highly stereocontrolled process. The related n-pentenyl derivatives are unique in that either the orthoester (NPOE) or its rearrangement product (NPGAC) can function as a glycosyl donor, and mechanistic considerations indicate that both should (or could!) lead to the same product(s) arising from trans-orthoesterification, glycosidation, glycosyl esterification, etc. Experiments are described which show that the product obtained from a given reaction can be optimized by careful choice of the donor, NPOE or related NPGAC, and careful attention to reaction conditions, electrophilic promoter, 'size' of the glycosyl acceptor, and experimental protocol.
- Mach, Mateusz,Schlueter, Urs,Mathew, Felix,Fraser-Reid, Bert,Hazen, Kevin C
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p. 7345 - 7354
(2007/10/03)
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- Stereoselective synthesis of 2-hydroxy-alpha-mannopyranosides from glucal donors.
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[figure: see text] Direct synthetic access to 2-hydroxy-alpha-mannopyranosides from glucal donors is accomplished via a one-pot stereoselective oxidative glycosylation reaction, employing the reagent combination of dibenzothiophene bis(triflate) and dibenzothiophene-5-oxide.
- Kim,Di Bussolo,Gin
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p. 303 - 306
(2007/10/03)
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- Silyl group migration in 1-O-silyl protected sugars-convenient synthesis of 2-O-unprotected sugars
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Reaction of 2-O-unprotected 1-9-silyl-protected D-glucose and D-galactose derivatives 5a-d with benzyl bromide in the presence of sodium hydride as the base afforded 1-O-benzyl 2-O-silyl derivatives 6aα/β - 6dα/β. Thus, prior to anomeric O-benzylation, t
- Lassaletta, Jose M.,Meichle, Michaela,Weiler, Sven,Schmidt, Richard R.
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p. 241 - 254
(2007/10/03)
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- The synthesis and characterization of 2-O-(6-O-L-glycero-α,β-D-manno-heptopyranosyl-α-D-glucopyranosyl)-α,β-D-glucopyranose
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The title compounds were synthesized, and appropriate derivatives were characterized by GLC, GLC-MS, and NMR spectroscopy.The GLC and GLC and GLC-MS data proved 2-O-(6-O-L-glycero-α-D-manno-heptopyranosyl-α-D-glucopyranosyl)-D-glucopyranose to be a consti
- Nopogodev, Sergey A.,Pakulski, Zbigniew,Zamojski, Aleksander,Holst, Otto,Brade, Helmut
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- SYNTHESIS OF KOJITETRAOSE AND KOJIPENTAOSE
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Kojitriose 2)-α-D-Glcp-(1->2)-D-Glcp>, kojitetraose, and kojipentaose have been synthesised by silver perchlorate-promoted Koenigs-Knorr type condensation, using 3,4,6-tri-O-acetyl-2-O-allyl-β-D-glucopyranosyl chloride and hepta-O-acetyl-β-k
- Takeo, Ken'Ichi,Suzuki, Yukiko
-
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- Syntheses of Acetylated Terasaccharides, Manα1->2Manα1->3Manβ1->4GlcNAc and Manα1->3Manα1->6Manβ1->4GlcNAc
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As a preliminary experiment aimed ultimately at the total syntheses of high mannose-type oligosacharides in glycoproteins, two fully acetylated tetrasaccharides.Manα1->2Manα1->3Manβ1->4GlcNAc (32) and Manα1->3Manα1->6Manβ1->4GlcNAc (35), were synthesized
- Itoh, Yoshio,Tejima, Setsuzo
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p. 957 - 966
(2007/10/02)
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- SYNTHESIS OF LINEAR D-MANNOTETRAOSE AND D-MANNOHEXAOSE, PARTIAL STRUCTURES OF THE CELL-SURFACE D-MANNAN OF Candida albicans AND Candida utilis
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Syntheses of linear D-manno-oligosaccharides, O-α-Man-(1-2)-O-α-Man-(1-2)-O-α-Man-(1-2)-Man and O-α-Man-(1-2)-O-α-Man-(1-2)-O-α-Man-(1-2)-O-α-Man-(1-2)-Man, which correspond to part of the structure of the cell-wall D-mannan chain of Candida utilis and Ca
- Ogawa, Tomoya,Yamamoto, Hisao
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p. 271 - 284
(2007/10/02)
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