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Your search keyword '"Masanori Tanahashi"' showing total 5 results
Start Over Author "Masanori Tanahashi" Topic biochemistry
5 results on '"Masanori Tanahashi"'

3. Conjugates of biologically active lipid a-subunit analogs with 3-deoxy-d-manno-2-octulosonic acid (KDO) and its methyl ester

Author

Yuji Ogawa, Akira Hasegawa, Yushun Fujishima, Makoto Kiso, Masanori Tanahashi, Frank M. Unger, and Fujita Minoru

Subjects
chemistry.chemical_classification, Anomer, Stereochemistry, Organic Chemistry, Disaccharide, Diastereomer, Glycoside, General Medicine, Biochemistry, Thin-layer chromatography, Analytical Chemistry, chemistry.chemical_compound, chemistry, Glucosamine, Bromide, Glycosyl
Abstract

The previously described, biologically active 4- O -phosphono- d -glucosamine derivatives GLA-27, GLA-47, and GLA-60 (all related to bacterial lipid A) were converted into their respective conjugates with 3-deoxy- d - manno -2-octulosonic acid (KDO). The methyl and benzyl esters of [4,5,7,8-tetrakis- O -(chloroacetyl)-3-deoxy- d - manno -2-octulopyranosyl fluoride]onic acid and the corresponding glycosyl bromide were prepared, by starting from methyl 2,4,5,7,8-penta- O -acetyl-3-deoxy- d - manno -2-octulopyranosonate, and coupled to O-6 of suitably protected precursors of the phosphono- d -glucosamines. This gave a series of fully substituted disaccharides that were transformed, by O-de(chloroacetyl)ation and successive hydrogenolytic removal of benzyl, benzyloxymethyl, and phenyl groups, into the target conjugates (KDO methyl ester α- and β-linked to GLA-27, and KDO α-linked to GLA-27, GLA-47, and GLA-60).

Published
1988

4. 6-O-glycosylation of a lipid A-subunit analog (GLA-27) with methyl (4,5,7,8-tetra-O-acetyl-3-deoxy-α-d-manno-2-octulopyranosyl bromide)onate (a KDO derivative)

Author

Masanori Tanahashi, Makoto Kiso, Frank M. Unger, and Akira Hasegawa

Subjects
Glycosylation, biology, Stereochemistry, Organic Chemistry, Disaccharide, General Medicine, Nuclear magnetic resonance spectroscopy, biology.organism_classification, Biochemistry, Analytical Chemistry, Lipid A, chemistry.chemical_compound, chemistry, Bromide, Aldonic acid, Tetra, Derivative (chemistry)
Published
1987

5. Synthesis of 2-deoxy-4-O-phosphono-3-O-tetradecanoyl-2-[(3R- and (3S)-3-tetradecanoyloxytetradecanamido]-d-glucose: a diastereoisomeric pair of 4-O-phosphono-d-glucosamine derivatives (GLA-27) related to bacterial lipid A

Author

Makoto Kiso, Masanori Tanahashi, Yuji Ogawa, Akira Hasegawa, Yushun Fujishima, and Shinji Tanaka

Subjects
chemistry.chemical_classification, Magnetic Resonance Spectroscopy, Optical Rotation, Chemistry, Stereochemistry, Organic Chemistry, Aminoglycoside, Stereoisomerism, General Medicine, Nuclear magnetic resonance spectroscopy, Biochemistry, Analytical Chemistry, Lipid A, chemistry.chemical_compound, Aldose, Glucosamine, D-Glucose, Indicators and Reagents, D-Glucosamine
Abstract

The diastereoisomeric, 4-O-phosphono- d -glucosamine derivatives named in the title have been synthesized, starting from benzyl 2-amino-2-deoxy-4,6-O-isopropylidene-β- d -glucopyranoside and (3RS)-3-hydroxytetradecanoic acid.

Published
1986

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