- The effect of deoxyfluorination and: O -acylation on the cytotoxicity of N -acetyl-d-gluco- And d-galactosamine hemiacetals
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Fully acetylated deoxyfluorinated hexosamine analogues and non-fluorinated 3,4,6-tri-O-acylated N-acetyl-hexosamine hemiacetals have previously been shown to display moderate anti-proliferative activity. We prepared a set of deoxyfluorinated GlcNAc and GalNAc hemiacetals that comprised both features: O-acylation at the non-anomeric positions with an acetyl, propionyl and butanoyl group, and deoxyfluorination at selected positions. Determination of the in vitro cytotoxicity towards the MDA-MB-231 breast cancer and HEK-293 cell lines showed that deoxyfluorination enhanced cytotoxicity in most analogues. Increasing the ester alkyl chain length had a variable effect on the cytotoxicity of fluoro analogues, which contrasted with non-fluorinated hemiacetals where butanoyl derivatives had always higher cytotoxicity than acetates. Reaction with 2-phenylethanethiol indicated that the recently described S-glyco-modification is an unlikely cause of cytotoxicity.
- Hamala, Vojtěch,?ervenková ??astná, Lucie,Kurfi?t, Martin,Cu?ínová, Petra,Balouch, Martin,Hrstka, Roman,Voňka, Petr,Karban, Jind?ich
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supporting information
p. 4497 - 4506
(2021/05/31)
-
- Monosaccharide inhibitors targeting carbohydrate esterase family 4 de-N-acetylases
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The Carbohydrate Esterase family 4 contains virulence factors which modify peptidoglycan and biofilm-related exopolysaccharides. Despite the importance of this family of enzymes, a potent mechanism-based inhibition strategy has yet to emerge. Based on the postulated tridentate binding mode of the tetrahedral de-N-acetylation intermediate, GlcNAc derivatives bearing metal chelating groups at the 2 and 3 positions were synthesized. These scaffolds include 2-C phosphonate, 2-C sulfonamide, 2-thionoacetamide warheads as well as derivatives bearing thiol, amine and azide substitutions at the 3-position. The inhibitors were assayed against a representative peptidoglycan deacetylase, Pgda from Streptococcus pneumonia, and a representative biofilm-related exopolysaccharide deacetylase, PgaB from Escherichia coli. Of the inhibitors evaluated, the 3-thio derivatives showed weak to moderate inhibition of Pgda. The strongest inhibitor was benzyl 2,3-dideoxy-2-thionoacetamide-3-thio-β-D-glucoside, whose inhibitory potency showed an unexpected dependence on metal concentration and was found to have a partial mixed inhibition mode (Ki = 2.9 ± 0.6 μM).
- DiFrancesco, Benjamin R.,Morrison, Zachary A.,Nitz, Mark
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p. 5631 - 5643
(2018/10/24)
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- Syntheses of N-aryl-protected glucosamines and their stereoselectivity in chemical glycosylations
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N-Aryl-protecting groups were introduced in glucosamines to achieve β-selective glycosylation. Various N-aryl aminosugars were synthesized via Buchwald–Hartwig reaction. Glycosylation using glycosyl trichloroacetimidates of N-aryl aminosugars smoothly proceeded in the presence of trimethylsilyl trifluoromethanesulfonate. Use of a glycosyl donor comprising an electron-donating 2,4-dimethoxyphenyl (DMP) group led to the glycosylation proceeding with high β selectivity. This stereoselectivity seemed to be derived from the formation of an aziridine intermediate. The DMP-protecting group can be removed immediately by using ammonium hexanitratocerate (IV).
- Otsuka, Yuji,Yamamoto, Toshihiro,Fukase, Koichi
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p. 3019 - 3023
(2017/07/17)
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- Synthesis of lipo-chitooligosaccharide analogues and their interaction with LYR3, a high affinity binding protein for Nod factors and Myc-LCOs
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Lipo-chitotetrasaccharide analogues where one central GlcNAc residue was replaced by a triazole unit have been synthesized from a derivative obtained by chitin depolymerization and a functionalized N-acetyl-glucosamine via the copper-catalyzed azide-alkyn
- Berthelot, Nathan,Brossay, Antoine,Gasciolli, Virginie,Bono, Jean-Jacques,Baron, Aurélie,Beau, Jean-Marie,Urban, Dominique,Boyer, Fran?ois-Didier,Vauzeilles, Boris
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supporting information
p. 7802 - 7812
(2017/10/06)
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- Ceric ammonium nitrate/acetic anhydride: A tunable system for the O-acetylation and mononitration of diversely protected carbohydrates
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Esterification of a wide range of partially protected carbohydrate derivatives was achieved using acetic anhydride and a catalytic amount of ceric ammonium nitrate (CAN). Compatibility with the commonly used protecting groups was demonstrated, with the es
- Seepersaud, Mohindra,Seecharan, Savita,Lalgee, Lorale J.,Jalsa, Nigel Kevin
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supporting information
p. 853 - 871
(2017/04/27)
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- Chemoenzymatic Synthesis of 4-Fluoro-N-Acetylhexosamine Uridine Diphosphate Donors: Chain Terminators in Glycosaminoglycan Synthesis
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Unnatural uridine diphosphate (UDP)-sugar donors, UDP-4-deoxy-4-fluoro-N-acetylglucosamine (4FGlcNAc) and UDP-4-deoxy-4-fluoro-N-acetylgalactosamine (4FGalNAc), were prepared using both chemical and chemoenzymatic syntheses relying on N-acetylglucosamine-
- Schultz, Victor L.,Zhang, Xing,Linkens, Kathryn,Rimel, Jenna,Green, Dixy E.,Deangelis, Paul L.,Linhardt, Robert J.
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p. 2243 - 2248
(2017/02/26)
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- Direct glycosylation of unprotected and unactivated sugars using bismuth nitrate pentahydrate
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Bi(NO3)3, a low-cost, mild, and environmentally green catalyst, has been successfully utilized for Fischer glycosylation for the synthesis of alkyl/aryl glycopyranosides by reacting unprotected sugars, namely, D-glucose, L-rhamnose, D-galactose, D-arabinose, and N-acetyl-D-glucosamine with various alcohols in good to excellent yields. The glycosides were formed with high α-selectivity. Further, an expedient separation of α- and β-glycosides using silver nitrate-impregnated silica gel flash liquid chromatography has been developed.
- Polanki, Innaiah K.,Kurma, Siva H.,Bhattacharya, Asish K.
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p. 196 - 205
(2015/06/08)
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- Order of reactivity of OH/NH groups of glucosamine hydrochloride and N -Acetyl glucosamine toward benzylation using NaH/BnBr in DMF
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The order of reactivity of OH and NH groups of glucosamine hydrochloride (GlcNH2HCl) and N-acetyl glucosamine (GlcNAc) toward benzylation with NaH/BnBr in DMF was investigated. For GlcNH2.HCl, benzyl groups were introduced in the order of N-Bn > N-Bn2 > 1-O-Bn > 6-O-Bn > 4-O-Bn > 3-O-Bn; for GlcNAc, benzyl groups were introduced in the order of 1-O-Bn > 6-O-Bn > 4-O-Bn > 3-O-Bn > N-Bn. A range of partially benzylated 2-N,N′-dibenzyl glucopyranosides and GlcNAc derivatives were obtained in a single step. Taylor & Francis Group, LLC.
- Ali, Stacy P.,Jalsa, Nigel Kevin
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p. 185 - 196
(2014/06/09)
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- N-Acetylglucosamine-based efficient, phase-selective organogelators for oil spill remediation
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Two simple, eco-friendly and efficient phase-selective gelators were developed for instant (45 s) gelation of oil (either commercial fuels or pure organic liquids) from an oil-water mixture at room temperature to combat marine oil spills.
- Mukherjee, Somnath,Shang, Congdi,Chen, Xiangli,Chang, Xingmao,Liu, Kaiqiang,Yu, Chunmeng,Fang, Yu
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supporting information
p. 13940 - 13943
(2015/02/19)
-
- Synthesis of modified peptidoglycan precursor analogues for the inhibition of glycosyltransferase
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The peptidoglycan glycosyltransferases (GTs) are essential enzymes that catalyze the polymerization of glycan chains of the bacterial cell wall from lipid II and thus constitute a validated antibacterial target. Their enzymatic cavity is composed of a donor site for the growing glycan chain (where the inhibitor moenomycin binds) and an acceptor site for lipid II substrate. In order to find lead inhibitors able to fill this large active site, we have synthesized a series of substrate analogues of lipid I and lipid II with variations in the lipid, the pyrophosphate, and the peptide moieties and evaluated their biological effect on the GT activity of E. coli PBP1b and their antibacterial potential. We found several compounds able to inhibit the GT activity in vitro and cause growth defect in Bacillus subtilis. The more active was C16-phosphoglycerate-MurNAc-(l-Ala-d-Glu)-GlcNAc, which also showed antibacterial activity. These molecules are promising leads for the design of new antibacterial GT inhibitors.
- Dumbre, Shrinivas,Derouaux, Adeline,Lescrinier, Eveline,Piette, Andre,Joris, Bernard,Terrak, Mohammed,Herdewijn, Piet
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p. 9343 - 9351
(2012/07/14)
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- Synthesis and protective effects of aralkyl alcoholic 2-acetamido-2-deoxy- β-d-pyranosides on hypoglycemia and serum limitation induced apoptosis in PC12 cell
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Neuroprotective agents have been in the focus of attention in the treatment of ischemic stroke. Salidroside, a phenylpropanoid glycoside isolated from Rhodiola rosea L., possessed a wide range of biological activities, especially neuroprotection. In an at
- Meng, Ying,Guo, Yibing,Ling, Yong,Zhao, Yahong,Zhang, Qi,Zhou, Xinyang,Ding, Fei,Yang, Yumin
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experimental part
p. 5577 - 5584
(2011/10/13)
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- Design and synthesis of unnatural heparosan and chondroitin building blocks
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Triazole linked heparosan and chondroitin disaccharide and tetrasaccharide building blocks were synthesized in a stereoselective manner by applying a very efficient copper catalyzed azide-alkyne cycloaddition (CuAAC) reaction of appropriately substituted
- Bera, Smritilekha,Linhardt, Robert J.
-
experimental part
p. 3181 - 3193
(2011/06/24)
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- Total synthesis of polyprenyl N-Glycolyl Lipid II as a mycobacterial transglycosylase substrate
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A feasible synthetic approach toward the Mycobacterium tuberculosis (Mtb) N-glycolyl lipid II-like molecule 1 is described. Compound 1 bears pendant undecaprenol and L-lysin moieties instead of the naturally occurring decaprenol and meso-diaminopimelic ac
- Meng, Fan-Chun,Chen, Kuo-Ting,Huang, Lin-Ya,Shih, Hao-Wei,Chang, Han-Hui,Nien, Fu-Yao,Liang, Pi-Hui,Cheng, Ting-Jen R.,Wong, Chi-Huey,Cheng, Wei-Chieh
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supporting information; experimental part
p. 5306 - 5309
(2011/12/15)
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- H2so4-silica promoted direct formation of β-glycosides of N-Acetyl glycosylamines under microwave conditions
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N-Acetyl glycosamines are important building blocks for the synthesis of biologically active oligosaccharides. This communication describes a simple direct protocol for the synthesis of βglycosides of N-acetyl glycosylamines from easily accessible perO-ac
- Mandai, Santanu,Sharma, Nayan,Mukhopadhyay, Balaram
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experimental part
p. 3111 - 3114
(2010/03/03)
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- Direct formation of β-glycosides of N-acetyl glycosamines mediated by rare earth metal triflates
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A direct, mild and efficient protocol for the preparation of β-glycosides of N-acetyl glucosamine (GlcNAc) and N-acetyl galactosamine (GalNAc) has been developed using peracetylated β-GlcNAc and β-GalNAc as donors. All rare Earth metal triflate promoters
- Christensen, Helle,Christiansen, Mira Steinicke,Petersen, Jette,Jensen, Henrik Helligso
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supporting information; experimental part
p. 3276 - 3283
(2009/02/05)
-
- A very simple synthesis of GlcNAc-α-pyrophosphoryl-decanol: A substrate for the assay of a bacterial galactosyltransferase
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Lipid-linked sugar pyrophosphates, such as GlcNAc-pyrophosphoryl undecaprenol, are important intermediates in the biosynthesis of cell-surface bacterial polysaccharides. It was recently demonstrated that much simpler lipids could substitute for undecaprenol while retaining biological activity, thus making efficient synthetic access to this class of compounds highly desirable. In order to facilitate the synthesis of pure substrates for bacterial glycosyltransferases, we have developed a simple 'two-pot' synthesis which we demonstrate here for GlcNAc-α-pyrophosphoryl-decanol (4). GlcNAc pyrophosphate, produced by mild periodate oxidation/β-elimination of commercial UDP-GlcNAc, is alkylated using 1-iododecane to yield the target compound 4 in 39% yield. Compound 4 is shown to be an efficient acceptor for a bacterial galactosyltransferase.
- Brockhausen, Inka,Larsson, E. Andreas,Hindsgaul, Ole
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p. 804 - 807
(2008/09/18)
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- Influence on the enantioselectivity in allylic alkylation of the anomeric position of the phosphine-amide ligands derived from d-glucosamine
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The synthesis of a new series of chiral phosphine amides derived from d-glucosamine is described. The palladium-catalyzed asymmetric allylic alkylations of racemic (E)-1,3-diphenyl-2-propenyl acetate with dimethyl malonate using these ligands have been in
- Glego?a, Katarzyna,Framery, Eric,Goux-Henry, Catherine,Micha? Pietrusiewicz,Sinou, Denis
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p. 7133 - 7141
(2008/02/07)
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- Identification of a UDP-Gal: GlcNAc-R galactosyltransferase activity in Escherichia coli VW187
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A novel acceptor substrate for galactosyltransferase was synthesized containing GlcNAcα-pyrophosphate, covalently bound to a hydrophobic phenoxyundecyl moiety (GlcNAc α-O-PO3-PO3-(CH 2)11-O-Phenyl). The new subs
- Montoya-Peleaz, Pedro J.,Riley, John G.,Szarek, Walter A.,Valvano, Miguel A.,Schutzbach, John S.,Brockhausen, Inka
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p. 1205 - 1211
(2007/10/03)
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- Modifying the regioselectivity of glycosynthase reactions through changes in the acceptor
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Successful glycosynthase-mediated reactions have been performed on 6-O-benzyl-, 6-O-(4-nitrobenzyl)-, and 6-O-benzoyl-D-glucopyranose to give 1,2-β- and 1,3-β-D-glycosylated products; 4-O-benzyl-D-xylopyranose gave only a 1,2-β-glycosylated product. A rat
- Stick, Robert V.,Stubbs, Keith A.,Watts, Andrew G.
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p. 779 - 786
(2007/10/03)
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- A practical method for preparation of β-glycosides of N-acetylglucosamine
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A mild and efficient method for preparation of GlcNAc derivatives by reaction of glycosyl acceptors with glycosyl oxazolines has been developed. The key feature is use of Yb(OTf)3 as promoter, requiring moderate reaction times and equivalence s
- Crasto, Curtis F.,Jones, Graham B.
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p. 4891 - 4894
(2007/10/03)
-
- Elucidation of the mechanism of polysaccharide cleavage by chondroitin AC lyase from Flavobacterium heparinum
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Chondroitin AC lyase from Flavobacterium heparinum degrades chondroitin sulfate glycosaminoglycans via an elimination mechanism resulting in disaccharides or oligosaccharides with Δ4,5-unsaturated uronic acid residues at their nonreducing end. Mechanistic details concerning the ordering of the bond-breaking and -forming steps of this enzymatic reaction are nonexistent, mainly due to the inhomogeneous nature of the polymeric substrates. The creation of a new class of synthetic substrates for this enzyme has allowed the measurement of defined and reproducible kcat and Km values and has expanded the range of mechanistic studies that can be performed. The primary deuterium kinetic isotope effect upon kcat/Km for the abstraction of the proton α to the carboxylic acid was measured to be 1.67 ± 0.07, showing that deprotonation occurs in a rate-limiting step. Using substrates with leaving groups of differing reactivity, a flat linear free energy relationship was produced, indicating that the C4-O4 bond is not broken in a rate-determining step. Taken together, these results strongly suggest a stepwise mechanism. Consistent with this was the measurement of a secondary deuterium kinetic isotope effect upon kcat/Km of 1.01 ± 0.03 on a 4-{2H}-substrate, indicating that no sp2 character is developed at C4 during the rate-limiting step, thereby ruling out a concerted syn-elimination.
- Rye, Carl S.,Withers, Stephen G.
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p. 9756 - 9767
(2007/10/03)
-
- Solid-phase oligosaccharide synthesis with tris(alkoxy)benzyl amine (BAL) safety-catch anchoring
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A tris(alkoxy)benzylamine (BAL) handle strategy was developed for safety-catch anchoring of D-glucosamine derivatives in solid-phase synthesis of oligosaccharides; the linkage between the BAL handle and the amine proved stable to conc. TFA and Lewis acids, but after N-acylation the amide could be released by treatment with TFA-H2O (19:1).
- Tolborg, Jakob F.,Jensen, Knud J.
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p. 147 - 148
(2007/10/03)
-
- Chemical synthesis of N-acetylglucosamine derivatives and their use as glycosyl acceptors by the Mesorhizobium loti chitin oligosaccharide synthase NodC
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Rhizobial bacteria synthesize lipo-chitin oligosaccharide signal molecules (Nod factors) that are essential for the formation of symbiotic organs on the roots of host plants, a process known as nodulation. Biosynthesis of the chitin oligosaccharide moiety
- Kamst, Eric,Zegelaar-Jaarsveld, Korien,Van Der Marel, Gijs A.,Van Boom, Jacques H.,Lugtenberg, Ben J.J.,Spaink, Herman P.
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p. 176 - 189
(2007/10/03)
-
- Access to molecular diversity in glycosaminoglycans: Combinatorial synthesis of eight chondroitin sulfate disaccharides
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Glycosaminoglycans (GAGs), linear sulfated oligosaccharides, are involved in numerous biological events ranging from tissue structure to protein activity regulation. The combinatorial nature of their oligosaccharidic framework and sulfatation pattern (sul
- Lubineau, Andre?,Bonnaffe?, David
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p. 2523 - 2532
(2007/10/03)
-
- Use of sodium iodide and crown ether in the synthesis of N-acetylglucosamine glycosides
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A pair of sodium iodide-crown ether reagents was used in the synthesis of N-acetylglucosamine glycosides. At room temperature, the reaction resulted in β-glycosides, whereas at 85-90°C, it gave a mixture of anomers or α-anomer only.
- Kur'yanov,Zemlyakov,Chupakhina,Chirva
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p. 282 - 283
(2007/10/03)
-
- Use of cyclic sulfamidates derived from D-allosamine in nucleophilic displacements: Scope and limitations
-
A cyclic 2,3-sulfamidate derived from N-acetyl-D-allosamine has been treated with a variety of S-. N-, O-. and C-nucleophiles, leading to nucleophilic displacement at C-3, elimination, or deacetylation reactions depending on the type of nucleophile used. Nucleophilic displacement is achieved with thio-nucleophiles and NaN3. allowing the preparation of 3-thio- or 3-azido glucosamine derivatives difficult to obtain by use of sulfonates.
- Aguilera, Begona,Fernandez-Mayoralas, Alfonso,Jaramillo, Carlos
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p. 5863 - 5876
(2007/10/03)
-
- Processes for the synthesis of sialyl Lewisx compounds
-
Disclosed are processes for the chemical synthesis of sialyl Lewisx -Y compounds where Y is --OH, --NHR, --SH, --SR or --OR, and R is an aglycon of at least one carbon atom.
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-
- New procedure for the preparation of 2-(trimethylsilyl)ethyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside and other alkyl β-glycosides
-
The title compound and other alkyl β-glycosides 1a-g can be prepared in one step from commercially available 2-acetamido-2-deoxy-1,3,4,6-tetra-O-acetyl-β-D-glucopyranose (3) and simple alcohols using camphorsulfonic acid as a promoter together with azeotr
- Sowell, C. Gregory,Livesay, Mark T.,Johnson, David A.
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p. 609 - 610
(2007/10/02)
-
- Preparations and reactions of acylated and partially acylated glycosyl fluorides
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Partial acylation of glycosyl fluorides in the galacto (2 and 3) and gluco series (8-10) is readily achieved. Attempts to further alkylate these acyl derivatives failed. Treatment of 2 with Lewis acid, however, provided a facile route to the 1,4-anhydro derivative 5. Lewis acid-mediated glycosylation of 2-acetamido-3,4,6-tri-O-acetyl-α-D-glucopyranosyl fluoride 11 led to the simple glycosides and thioglycosides 12-16. Similarly, in the galacto series (17) an advantageous route to the β-galactosidase inhibitor 19 could be elaborated.
- Thiem, Joachim,Wiesner, Matthias
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p. 197 - 206
(2007/10/02)
-
- Syntheses of model oligosaccharides of biological significance. XII. Synthesis, NMR, and conformational analysis of trideuteriomethyl 4-O-(β-D-mannopyranosyl)-2-acetamido-2-deoxy-β-D-glucopyranoside: the use of DEPT 1H to 13C transfer for T1 measurements and NOE assignments of ...
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The title disaccharide Manp(β1-4)GlcpNAcβ1-OCD3 has been prepared by a short synthetic sequence through the inversion of configuration from gluco to manno involving benzyl Glcp(β1-4)GlcpNAc.The disaccharide was subjected to detailed high-field 1H and 13C NMR study.First, conventional and 2D spectra were run to afford a complete set of assigned spectral parameters.Next, steady-state 1H- NOE and 1H, 13C spin lattice relaxation experiments were performed to infer dynamic spectral data related to molecular conformation.Owing to tight couplings and signal overlaps in the 1H spectrum, proton relaxation and selected NOE data were obtained via 13C NMR after transfer of the actual, non-equilibrium, proton magnetization to the 13C frequency domain.Using this experimental approach it has been found that T1's for Manp H-4 and GlcpNAc H-2 were substantially longer than those of the other sugar ring protons, and that the principal interresidue dipolar contact in Manp(β1-4)GlcpNAcβ1-OCD3 takes place between Manp H-1 and GlcpNAc H-4.Subsequently, a conformational analysis of the disaccharide was executed by means of a semiempirical method comparing Boltzman-averaged computed observables with experimental T1 and NOE values.The results suggest that the disaccharide has substantial conformational flexibility.Its exo-anomeric-stabilized conformational minimum at approximately Φ = +50 deg (Ψ = 0 +/- 10 deg) of the glycosidic rotational angle is significantly populated but this global minimum does not represent the only rotational form available to the molecule.
- Lee, Ho Huat,Congson, Ligaya N.,Whitfield, Dennis M.,Radics, Lajos R.,Krepinsky, Jiri J.
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p. 2607 - 2617
(2007/10/02)
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- Synthesis of N-acetylsugar-β-trans-glycosides: Facile one-pot transglycosylation of epoxypentyl tri-0-acetyl-N-acetylglucosamine
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Glycosides 10 and 11 were prepared from epoxypentyl β-D-N-acetylglucosamine 8 under mild conditions, using TMS triflate as the promotor. Presumably, this novel reaction proceeds via in situ activation of the intermediate oxazoline 9.
- Boldt,Schumacher-Wandersleb,Peter
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p. 1413 - 1416
(2007/10/02)
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- 1,3,4,6-Tetra-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranose as a glycosyl donor in syntheses of oligosaccharides
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1,3,4,6-Tetra-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranose was tested as a glycosyl donor for oligosaccharide synthesis via ferric chloride-catalyzed coupling reaction.Glycosyl acceptors tried (6 in all) were O-benzyl-protected D-galactosides having free OH groups at positions 3 and 4, respectively, and similarly protected glycosides of D-glucose and 2-acetamido-2-deoxy-D-glucose unsubstituted on O-4.Existing syntheses of all the acceptors were improved, in four instances by exploitation of Garegg and Hultberg's cyanoborohydride procedure for the conversion 4,6-O-benzylidene -> 6-O-benzyl .Good to excellent yields of β-linked disaccharides were obtained from the galactoside and glucoside acceptors, but with allyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside, stereoselectivity was lost (α:β-ratio 1:2).Allyl and benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosides gave, respectively, the allyl and benzyl β-glycosides of the donor as major products.A mechanism is proposed for this transglycosidation reaction.The N-chloroacetyl groups in the disaccharide products were readily converted into N-acetyl by reduction with zinc-acetic acid.
- Dasgupta, Falguni,Anderson, Laurens
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p. 239 - 255
(2007/10/02)
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- A NEW SYNTHESIS OF 1,2-TRANS-2-ACETAMIDO-2-DEOXYGLYCOPYRANOSIDES VIA 1,2-TRANS-2-DEOXY-2-IODOGLYCOSYL AZIDES
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Trans-addition of iodoazide to the double bond of 3,4,6-tri-O-acetyl-1,5-anhydro-D-arabino-hex-1-enitol yielded 2-deoxy-2-iodoglycosyl azides, which are percursors of 1,2-trans-2-amino-2-deoxyglycopyranosides when treated by an alcohol in the presence of triphenylphosphine.
- Lafont, Dominique,Guilloux, Pascal,Descotes, Gerard
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- Synthesis and biological activity of some 1-N-substituted 2-acetamido-2-deoxy-beta-D-glycopyranosylamine derivatives and related analogs.
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Several 1-N-substituted derivative [haloacetyl-, glycyl-, (dimethyl)amino-acetyl-, azidoacetyl-, trifluoroacetyl-, and trifluoromethylsulfonyl-] of 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-beta-D-glucopyranosylamine (1) were synthesized as potential metabolic inhibitors of cellular-membrane glycoconjugates. Several fully acetylated derivatives were found to inhibit growth of mouse mammary adenocarcinoma TA3, leukemia L1210, or leukemia P-288 cells at 1-0.01 mM concentration in vitro. Some of these derivatives were less active after O-deacetylation. Analogs of 1 in which NH2-1 was replaced by OH- or OAc-1 were also active on the same cell systems. The growth-inhibitory activity was correlated with inhibition of the incorporation of 2-amino-deoxy-D-glucose and L-leucine into a macromolecular fraction.
- Paul,Bernacki,Korytnyk
-
-