doi: 10.1271/bbb.57.1526.
Synthesis of 2-deoxy-2-[(2R,3S)-2-fluoro-3-hydroxytetradecanamido]- 3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-D-glucopyranose and its (2S,3R)-isomer
Affiliations
- PMID: 7764222
- DOI: 10.1271/bbb.57.1526
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Synthesis of 2-deoxy-2-[(2R,3S)-2-fluoro-3-hydroxytetradecanamido]- 3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-D-glucopyranose and its (2S,3R)-isomer
Biosci Biotechnol Biochem.
1993 Sep.
Free article
Abstract
2-Deoxy-2-[(2R,3S)-2-fluoro-3-hydroxytetradecanamido]-3-O-[( 3R)-3-hydroxytetradecanoyl]-4-O-phosphono-D-glucopyranose and its (2S,3R)-isomer were respectively synthesized from allyl 2-[(2R,3S)-3-(benzyloxycarbonyloxy)-2-fluorotetradecanamido] -2-deoxy-4,6-O-isopropylidene-beta-D-glucopyranoside and its corresponding (2S,3R)-isomer. Both target compounds did not activate macrophage, but the (2S,3R)-analogue strongly inhibited the binding of LPS to macrophage.
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