| DOI | Trouver le DOI : https://doi.org/10.1016/B978-0-12-746207-3.50017-6 |
|---|
| Auteur | Rechercher : Perry, Malcolm B.1; Rechercher : Williams, David T.1 |
|---|
| Affiliation | - Conseil national de recherches Canada
|
|---|
| Format | Texte, Chapitre de livre |
|---|
| Résumé | The synthesis of 3-deoxy-D-manno-octulosonic acid (KDO) (VIII) from D-mannose starts with the base catalyzed addition of nitromethane to D-mannose to give a mixture of l-deoxy-1-nitro-O-glycero-O-galactoheptitol (I) and l-deoxy-l-nitro-D-g/ycero-D-ta/o-heptitol (II). The acetylated crystalline I is boiled, in benzene solution, with sodium hydrogen carbonate to give crystalline pentaacetoxy-D-raafwo-l-nitro- 1-heptene (III) which is catalytically reduced to penta-0-acetyl-l,2-dideoxy-l-nitro-D-ma/i/to-heptitol (IV). Deacetylated IV is treated under modified Nef reaction conditions to yield 2-deoxy-D-raawzö-heptose (V). The 2-dœxy-O-manno-heptose is treated with aqueous sodium cyanide to yield a mixture of 3-deoxy-D-glycero-O-galacto-octonic acid (VI) and 3-deoxy-D-g/ycer0-D-ia/o-octonic acid (VII). The mixture of octonic acids (VI and VII) is smoothly oxidized with a modified vanadium chloride catalyst to give 3-deoxy-O-mannooctulosonic acid (VIII).
3-Deoxy-D-manno-octulosonic acid (VIII) [erroneously called 2-keto-3- deoxyoctonic acid (KDO) by some] was first detected by Levin and Racker and has since been shown to be a component of the lipopolysaccharides of gram-negative bacteria; it is considered that the so-called lipid A is joined through KD O to the "core" and polysaccharide portion of the molecule. The structure of KD O was established by Ghalambor and co-workers and was confirmed by the identification of 2-deoxy-D-manno-heptose as a degradation product and the identification of 3-dQOxy-O-glycero-O-galacto-octonic acid and 3-deoxy-O-glycero-O-talo-octomc acid as direct reduction products.
KDO has previously been made by the condensation of D-arabinose with oxaloacetic acid or di-/m-butyloxalacetic acid and by a route essentially the same as that described herein. |
|---|
| Date de publication | 1976 |
|---|
| Maison d’édition | ScienceDirect |
|---|
| Dans | |
|---|
| Série | |
|---|
| Note | Les auteurs étaient affiliés à la Division des sciences biologiques du CNRC au moment de la publication |
|---|
| Langue | anglais |
|---|
| Publications évaluées par des pairs | Oui |
|---|
| Numéro du CNRC | PERRY1976 |
|---|
| Numéro NPARC | 9369841 |
|---|
| Exporter la notice | Exporter en format RIS |
|---|
| Signaler une correction | Signaler une correction (s'ouvre dans un nouvel onglet) |
|---|
| Identificateur de l’enregistrement | 0ec81497-c362-4818-a3b5-97ec834271e5 |
|---|
| Enregistrement créé | 2009-07-10 |
|---|
| Enregistrement modifié | 2024-06-10 |
|---|
