- FLUORINATED N-ACETYL GLUCOSAMINE ANALOGS AND XYLOSE DERIVATIVES
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The present disclosure relates to analogs of N-acetyl glucosamine fluorinated at 4- and/or 6-position(s) and derivatives of xylose at anomeric position for the treatment of a neurological disease, inflammation, cancer and a central nervous system injury.
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Paragraph 0069; 00264-00265
(2019/12/25)
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- Hybrid solution/solid-phase synthesis of oligosaccharides by using trichloroacetyl isocyanate as sequestration-enabling reagent of sugar alcohols
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(Chemical Equation Presented) An excess of glycosyl acceptor is used in the solution-phase synthesis of oligosaccharides and any unconverted acceptor is removed by using trichloroacetyl isocyanate. A levulinoyl (Lev) ester group is then used as a masked tag in the following "resin-capture-release" purification strategy (see scheme).
- Dondoni, Alessandro,Marra, Alberto,Massi, Alessandro
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p. 1672 - 1676
(2007/10/03)
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- Preparation of O-Hydroxyethyl and O-Hydroxypropyl Derivatives of D-Glucose and 2-Acetamido-2-deoxy-D-glucose for Studies of Modified Hyaluronic Acid
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Some hydroxyethyl and hydroxypropyl derivatives of D-glucose and of 2-acetamido-2-deoxy-D-glucose have been sunthesized for use as reference substances for structural studies of hydroxyethylated and hydroxypropylated hyaluronic acid.Hydroxyethyl and hydroxypropyl substituents were introduced in the 2-O- or 3-O-position of D-glucose and in the 4-O- or 6-O-positions of 2-acetamido-2-deoxy-D-glucose by reaction of suitably protected sugars with either ethylene oxide or propylene oxide.For hydroxyethyl derivatives yields varied between 21 and 74percent and with a substantial portion of the doubly alkylated compounds.For hydroxypropyl derivatives yields varied between 15 and 80percent.Only trace amounts of the doubly alkylated compounds were found.The proportions of the respective derivatives were estimated using GLC-MS.All products were characterized by 1H and 13C NMR spectroscopy.
- Bjurling, Eva,Jansson, Per-Erik,Lindqvist, Bengt
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p. 589 - 595
(2007/10/02)
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- 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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- Bausteine von Oligosacchariden, XX. Synthese der Oligosaccharid-Determinanten der Blutgruppensubstanzen der Type 2 des ABH-Systems. Diskussion der &α-Glycosid-Synthese
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The antigenic determinants of type 2 of blood-group substances A and B (23 and 24) as well as blood-group substance H (17) were synthesized by selective glycosidation reactions combined with a series of blocking and deblocking steps.The possibilities and optimization of the α-glycoside synthesis are discussed.In hemagglutination inhibition tests the synthetic haptens A and B of type 2 and type 1 show a similar selective inhibitory effect.In case of hapten H, however, great differences can be observed.Here the type 2 exhibited a strong inhibition activity, whereas type 1 only showed an extremly low activity.This leads to the conclusion that in the determinants of the ABH-system on the surface of erythrocytes the chemical structure of type 2 is predominating.
- Paulsen, Hans,Kolar, Cenek
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p. 306 - 321
(2007/10/02)
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- Blood-group Ii-Active Oligosaccharides. Synthesis of a Tetrasaccharide, a β-(1->3) Dimer of N-Acetyl-lactosamine
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Condensation of benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (2) with 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide, followed by de-O-acetylation, acetonation, O-benzoylation, and acidic hydrolysis afforded the 3',4'-diol (5) derived from N-acetyl-lactosamine.This compound was selectively glycosylated at the 3'-position by the oxazoline (7) derived from lactosamine to give the protected tetrasaccharide (8) in 52percent yield.Removal of the protecting groups gave the free tetrasaccharide β-D-Galp-(1->4)-β-D-GlcpNAc-(1->3)-β-D-Galp-(1->4)-D-GlcpNAc (9), a β-(1->3) dimer of N-acetyl-lactosamine.This structure has been found in various glycolipids isolated from erythrocyte membranes and could be recognized by several anti-i antisera.
- Veyrieres, Alain
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p. 1626 - 1629
(2007/10/02)
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- Synthesis of carbohydrate analogs (positional, configurational, and optical) of n-acetylmuramoyl-L-alanyl-D-isoglutamine, and their immunoadjuvant activities.
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2-Acetamido-2-deoxy-4- and -6-O-(D-2-propanoyl-L-alanyl-D-isoglutamine)-D-glucopyranose, 2-acetamido-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine)-D-allopyranose, -D-gulopyranose, -D-galactopyranose, -D-mannopyranose, and -L-idopyranose, and 3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine)-D- and -L-glucopyranose were synthesized, in order to clarify the structural requirements for the immunoadjuvant activity of the carbohydrate moiety in N-acetylmuramoyl-L-alanyl-D-isoglutamine. Immunoadjuvant activity of the N-acetylmuramoyl-dipeptide analogs was examined in guinea-pigs.
- Hasegawa,Kaneda,Goh,Nishibori,Kiso,Azuma
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p. 143 - 163
(2007/10/02)
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