Pseudomonas aeruginosa / Rhamnolipid / One-pot two-step glycosylation / Chemoselectivity / Esterification / Carbohydrates N-iodosuccinimide/triflic acid mediated one-pot two-step hydroxydecanoate (13) gave rhamnolipid 17. The latter was transformed in five steps into the title compound 2. glycosylat
Synthesis of methyl 3-[3-(2-O-α-L-rhamnopyranosyl-α-L-rhamnopyranosyloxy)decanoyloxy]decanoate, a rhamnolipid from Pseudomonas aeruginosa
✍ Scribed by Pieter Westerduin; Paul E. de Haan; Michel J. Dees; Jacques H. van Boom
- Publisher
- Elsevier Science
- Year
- 1988
- Tongue
- English
- Weight
- 804 KB
- Volume
- 180
- Category
- Article
- ISSN
- 0008-6215
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Syntheses of the title glycosides are described. The critical O-glycosylations were carried out in the presence of boron trifluoride etherate with a high degree of alpha-selectivity.
Allyl 4-O-benzyl-~-L-rhamnopyranoside was converted into allyl 4-O-benzyl-3-O-methyl-oeL-rhamnopyranoside and this was condensed with 2,3,4-tri-O-acetyl-~-L-rhamnopyranosyl chloride to give a disaccharide derivative which was converted into allyl 4 This disaccharide derivative was condensed with 2,
The glycosphingolipids isolated from spermatozoa of a fresh-water bivalve, Hyriopsis schlegelii, have a unique structure containing one or two mannosyl residues, novel linkages including an internal fucopyranosyl residue, as well as terminal xylosyl and 4-O-methyl-D-glucopyranosyluronic acid groups.