55682-47-8Relevant academic research and scientific papers
Synthesis and in vitro cytotoxicity of acetylated 3-fluoro, 4-fluoro and 3,4-difluoro analogs of D-glucosamine and D-galactosamine
Horník, ?těpán,?t'astná, Lucie ?ervenková,Cu?ínová, Petra,Sykora, Jan,Káňová, Kate?ina,Hrstka, Roman,Císa?ová, Ivana,Dra?ínsky, Martin,Karban, Jind?ich
, p. 750 - 759 (2016/07/06)
Background: Derivatives of D-glucosamine and D-galactosamine represent an important family of the cell surface glycan components and their fluorinated analogs found use as metabolic inhibitors of complex glycan biosynthesis, or as probes for the study of protein-carbohydrate interactions. This work is focused on the synthesis of acetylated 3-deoxy-3-fluoro, 4-deoxy-4-fluoro and 3,4-dideoxy-3,4-difluoro analogs of D-glucosamine and D-galactosamine via 1,6-anhydrohexopyranose chemistry. Moreover, the cytotoxicity of the target compounds towards selected cancer cells is determined. Results: Introduction of fluorine at C-3 was achieved by the reaction of 1,6-anhydro-2-azido-2-deoxy-4-O-benzyl-β-D-glucopyranose or its 4-fluoro analog with DAST. The retention of configuration in this reaction is discussed. Fluorine at C-4 was installed by the reaction of 1,6:2,3-dianhydro-β-D-talopyranose with DAST, or by fluoridolysis of 1,6:3,4-dianhydro-2-azido-β-D-galactopyranose with KHF2. The amino group was introduced and masked as an azide in the synthesis. The 1-O-deacetylated 3-fluoro and 4-fluoro analogs of acetylated D-galactosamine inhibited proliferation of the human prostate cancer cell line PC-3 more than cisplatin and 5-fluorouracil (IC50 28 ± 3 μM and 54 ± 5 μM, respectively). Conclusion: A complete series of acetylated 3-fluoro, 4-fluoro and 3,4-difluoro analogs of D-glucosamine and D-galactosamine is now accessible by 1,6-anhydrohexopyranose chemistry. Intermediate fluorinated 1,6-anhydro-2-azido-hexopyranoses have potential as synthons in oligosaccharide assembly.
A Convenient Route to Peracetylated 3-Deoxy-3-fluoro Analogues of d -Glucosamine and d -Galactosamine from a ?erny Epoxide
Karban, Jind?ich,Horník, ?těpán,?ervenková ??astná, Lucie,Sykora, Jan
, p. 1253 - 1256 (2014/06/10)
Peracetylated 3-deoxy-3-fluoro analogues of d-glucosamine and d-galactosamine 3 and 4, respectively, were prepared from 1,6:2,3-dianhydro-4-O- benzyl-β-d-mannopyranose (6). Azidolysis of 6 followed by reaction with diethylaminosulfur trifluoride gave 1,6-
AN EFFICIENT AND SCALABLE PROCESS FOR THE MANUFACTURE OF FONDAPARINUX SODIUM
-
, (2013/08/15)
The present invention relates to a process for the synthesis of the Factor Xa anticoagulent Fondaparinux and related compounds. The invention relates, in addition, to efficient and scalable processes for the synthesis of various intermediates useful in the synthesis of Fondaparinux and related compounds.
Structure and stereochemistry of an anti-inflammatory anhydrosugar from the Australian marine sponge Plakinastrella clathrata and the synthesis of two analogues
Katavic, Peter L.,Yong, Ken W.L.,Herring, Joel N.,Deseo, Myrna A.,Blanchfield, Joanne T.,Ferro, Vito,Garson, Mary J.
, p. 8074 - 8079 (2013/08/23)
The structure and relative/absolute configuration of the C-15:0 iso-branched fatty acyl 1,6-anhydropyranose 1 isolated from the Australian marine sponge Plakinastrella clathrata have been investigated. Synthesis of the C-16:0 side chain-modified analogues
SYNTHETIC PENTASACCHARIDES HAVING SHORT HALF-LIFE AND HIGH ACTIVITY
-
Page/Page column 11, (2013/02/28)
The invention concerns a pentasaccharide compound of formula (I) and the salts thereof. The invention also concerns a pharmaceutical composition comprising the synthetic pentasaccharide compound of formula (I) and its salts. The invention further concerns
Total synthesis of n-acetylglucosamine-1,6-anhydro-n- acetylmuramylpentapeptide and evaluation of its turnover by ampd from escherichia coli
Hesek, Dusan,Lee, Mijoon,Zhang, Weilie,Noll, Bruce C.,Mobashery, Shahriar
supporting information; experimental part, p. 5187 - 5193 (2009/09/30)
The bacterial cell wall is recycled extensively during the course of cell growth. The first recycling event involves the catalytic action of thelytic transglycosylase enzymes, which produce an uncommon 1,6-anhydropy ranose moiety during separation of the muramyl residues from the peptidoglycan, the major constituent of the cell wall. This product, an N-acetyl-β-D-glucosamine- (1→4)-1,6-anhydro-N-acetyl-β-Dmuramylpeptide, is either internalized to initiate the recycling process or diffuses into the milieu to cause stimulation of the pro-inflammatory responses by the host. We report the total syntheses of N-acetyl-β-Dglucosamine-( 1→4)-1,6-anhydro-N-acetyl- β-D-muramyl-L-Ala-γ-D-Glu-meso-DAP-D-Ala-D-Ala (compound 1, the product of lytic transglycosylase action on the cell wall of Gram-negative bacteria) and N-acetyl-β-Dglucosamine-( 1→4)-1,6-anhydro-N-acetyl- β-D-muramyl-L-Ala-γ-D-Glu-L-Lys-D-Ala-D-Ala (compound 2, from lytic transglycosylase action on the cell wall of Gram-positive bacteria). The syntheses were accomplished in 15 linear steps. Compound 1 is shown to be a substrate of the AmpD enzyme of the Gram-negative bacterium Escherichia coli, anenzyme that removes the peptide from the disaccharide scaffold in the e arly cytoplasmic phase of cell wall turnover.
Synthesis of polynitrogenated analogues of glucopyranoses from levoglucosan
Bailliez, Vincent,Olesker, Alain,Cleophax, Jeannine
, p. 1079 - 1085 (2007/10/03)
Polynitrogenated analogues of glucopyranoses were synthesised from levoglucosan. These compounds are useful intermediates for the synthesis of new aminoglycoside mimetics.
Synthesis of muramyl peptides containing meso-diaminopimelic acid
Kubasch, Niels,Schmidt, Richard R.
, p. 2710 - 2726 (2007/10/03)
Chain-extension of L-glutamate aldehyde 3 by means of the Wittig-Horner reaction furnished the desired C7 dicarboxylic acid derivative, which in turn, after C-C double bond hydrogenation and protecting group manipulation, afforded the 2,6-diaminopimelic acid derivatives (S,R)-9 and (S,S)-9, both with the desired orthogonal protecting group pattern. Synthesis of the muramic acid derivative 15 and attachment of an L-alanine residue furnished muramyl-L-alanine 18. The corresponding 1,6-anhydromuramic acid derivative 26 was obtained similarly. Treatment of these compounds with peptides 28-30 and with the 2,6-diaminopimelic acid containing di- and tripeptides 32a, 32b, and 35 gave the protected muramyl peptides 17, 37, 40, 42, 44, 46, and 49a and 49b, which, after deprotection, afforded the desired target molecules muramyl-L-alanine (38), muramyl-L-alanyl-D-glutamic acid (39), muramyl-L-alanyl-D-glutaminide (41), muramyl-L-alanyl-D- isoglutaminyl-L-lysine (43), muramyl-L-alanyl-D-isoglutaminyl-(2S,6R)-2,6-diaminopimelic acid (45), muramyl-L-alanyl- L-isoglutaminyl-(2S,6R)-2,6-diaminopimelic-D-alanme (47), 1,6-anhydromuramyl-L-alanyl-D-isoglutaminyl-(2S,6R)-2,6-diaminopimelic acid (50a), and 1,6-anhydromuramyl-L-alanyl-D- isoglutaminyl-(2S,6S)-2,6-diaminiopimelic acid (50b). ( Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).
A facile synthesis of Cerny epoxides and selectively blocked derivatives of 2-azido-2-deoxy-β-D-glucopyranose
Xue, Jie,Guo, Zhongwu
, p. 6487 - 6489 (2007/10/03)
1,6:2,3-Dianhydro-β-D-glucopyranose and its 3-alkylated derivatives were prepared from D-glucal in one pot with overall isolated yields of 60-70%, and these Cerny epoxides were further conveniently converted to selectively blocked 2-azido-2-deoxy-β-D-glucopyranose derivatives by azido opening of the epoxide ring.
Synthesis and NMR spectra of 1,6-anhydro-2,3-dideoxy-2,3-epimino- and 1,6-anhydro-3,4-dideoxy-3,4-epimino-β-D-hexopyranoses
Karban, Jindrich,Budesinsky, Milos,Cerny, Miloslav,Trnka, Tomas
, p. 799 - 819 (2007/10/03)
A complete series of 2,3-dideoxy-2,3-epimino-and 3,4-dideoxy-3,4-epimino-1,6-anhydro-β-D-hexopyranoses were prepared by lithium aluminum hydride reduction of the corresponding trans-azido tosylates or trans-azido epoxides of 1,6-anhydro-β-D-hexopyranoses. The structure of the epimino derivatives was confirmed by 1H and 13C NMR spectra.
