- Methods for synthesis of alpha-d-gal (1~>3) gal-containing oligosaccharides
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This invention relates to reagents and methods for synthesis of biologically active di- and tri-saccharides comprising α-D-Gal(1→3)-D-Gal. In particular the invention provides novel reagents, intermediates and processes for the solution or solid phase synthesis of α-D-galactopyranosyl-(1→3)-D-galactose, and derivatives thereof. In one preferred embodiments the invention provides a protected monosaccharide building block of general formula (II): in which R3 is methoxy or methyl; R1 is H, benzoyl, pivaloyl, 4-chlorobenzoyl, acetyl, chloroacetyl, levulinoyl, 4-methylbenzoyl, benzyl, 3,4-methylenedioxybenzyl, 4-methoxybenzyl, 4-chlorobenzyl, 4-acetamidobenzyl, or 4-azidobenzyl; and R2 is H, Fmoc, benzoyl, pivaloyl, 4-chlorobenzoyl, acetyl, chloroacetyl, levulinoyl, 4-methylbenzoyl, benzyl, 3,4-methylenedioxybenzyl, 4-methoxybenzyl, 4-chlorobenzyl, 4-acetamidobenzyl, or 4-azidobenzyl.
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- Fluorinated glucosamine analogs useful for modulating post-translational glycosylations on cells
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The present invention provides compositions and methods for inhibiting cell migration, e.g., lymphocytes and inflammation. The invention also provides an improved process for preparing fluorinated N-acetylglucosamines.
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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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- Fluorinated carbohydrates as potential plasma membrane modifiers. Synthesis of 4- and 6-fluoro derivatives of 2-acetamido-2-deoxy-D-hexopyranoses.
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2-Amino-2,4-dideoxy-4-fluoro- and 2-amino-2,4,6-trideoxy-4, 6-difluoro-D-galactose, and 2-amino-2,4-dideoxy-4-fluoro- and 2-amino-4-deoxy-4, 4-difluoro-D-xylo-hexose were synthesized, as potential modifiers of tumor cell-surface glyco-conjugate, from benz
- Sharma,Bernacki,Paul,Korytnyk
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p. 205 - 221
(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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