Synthesis of azacyclic 2-deoxy-KDO
✍ Scribed by Daniel W. Norbeck; James B. Kramer
- Publisher
- Elsevier Science
- Year
- 1987
- Tongue
- French
- Weight
- 190 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Azacyclic analogues of 2-deoxy-KDO have been synthesized from KDO via reductive amination at C-2 and ring closure on C-6 with double inversion. CMP-KDO synthetasel catalyzes a key step in the biosynthesis of bacterial lipopolysaccharide.2 We and others3 anticipate that a novel class of antibiotics will emerge from inhibitors of this enzyme.
Kohlbrenner and Fesik4 recently demonstrated that the glycosidic linkage in CMP-KOO is 8.
📜 SIMILAR VOLUMES
CMP-Kdo synthetase' catalyzes a key step in the biosynthesis of bacterial lipopolysaccharide'. Recently, the 2-deoxy derivative of/LKdo (7) was reported to be a potent inhibitor of CMP-Kdo synthetase3. Two different syntheses of 7 have been reported4v5, the first involving hydrogenolysis of the glyc
A new synthesis for the 2-dcoxy KDO 2 by aldolic condmsation of 2,3:5,6diGi~ l-D-mmmo ald&yde. 4 with ethyl dituoacetate and cowersion of the cwdensation product to the f-dcoxyPdiam ester1Jinfourstepgisreponed.Rhodium(~decompositionofthediazocompoundleadsu,theu-enannaofthe 2dcoxy pyrawae 14 stereosp
## Abstract [(Benzyloxy)(benzyloxycarbonyl)methyl]triphenylphosphonium bromide (8), obtained from glyoxylic acid via a convenient one‐pot procedure, reacted in a Wittig reaction with 4‐__O__‐benzyl‐2,3:5,6‐di‐__O__‐isopropylidene‐D‐mannose (7), readily synthesized on a large scale from D‐mannose, t