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Synthesis of α-Kdo-(2→4)-Kdo disaccharide derivatives and their conjugation with a protected form of GLA-60, a biologically active analog of a lipid a subunit

✍ Scribed by Makoto Kiso; Minoru Fujita; Yuji Ogawa; Hideharu Ishida; Akira Hasegawa

Publisher: Elsevier Science
Year: 1990
Tongue: English
Weight: 997 KB
Volume: 196
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(90)84106-5

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✦ Synopsis

A variety of the protected O-[(3-deoxy-a-D-manno-2-octulopyranosyl)onic acid]-(2+4)-3-deoxy-D-marano-2octulosonic acid [a-Kdo-(2+4)-Kdo] derivatives have been synthesized starting from methyl [2-(trimethylsilyl)ethyl4,5,7,8-tetra-Oacetyl-3-deoxy-a-D-manno-2-octulopyranosid]onate. Some of these were conjugated with a protected form of a bacterial lipid A subunit-analog (GLA-60) having beneficial immunopharmacological activity, namely benzyl 2-[(3R)-3-(benzyloxymethoxy)tetradecanamido]-2-deoxy-4-O-(diphenoxyphosphinyl)-3-0-[(3R)-3-tetradecanoyloxytetradecanoyl]-/3-D-glucopyranoside. RESULTS AND DISCUSSION As previously described5, the 2-0-(tetrahydro-2-pyranyl) (2-O-TI-IP) deriva-*Presented at the XIVth International Carbohydrate Symposium,

📜 SIMILAR VOLUMES

6-O-glycosylation of a lipid A-subunit a

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)

✍ Makoto Kiso; Masanori Tanahashi; Akira Hasegawa; Frank M. Unger 📂 Article 📅 1987 🏛 Elsevier Science 🌐 English ⚖ 367 KB

3Deoxy-D-manno-2-octulosonic acid (KDO) is a prominent constituent of the cell-surface macromolecules of Gram-negative bacterial, and recently has also been found\* as a component of the cell walls of higher plants. In the bacterial lipopolysaccharides (US), KDO occurs as an cu-D-ketosidic component