title: A simple synthesis of 2-keto-3-deoxy-D-erythro-hexonic acid isopropyl ester, a key sugar for the bacterial population living under metallic stress.
abstract: 2-Keto-3-deoxy-D-erythro-hexonic acid (KDG) is the key intermediate metabolite of the Entner Doudoroff (ED) pathway. A simple, efficient and stereoselective synthesis of KDG isopropyl ester is described in five steps from 2,3-O-isopropylidene-D-threitol with an overall yield of 47%. KDG isopropyl ester is studied as an attractive marker of a functional Entner Doudoroff pathway. KDG isopropyl ester is used to promote growth of ammonium producing bacterial strains, showing interesting features in the remediation of heavy-metal polluted soils.
authors: ICMMO UMR 8182, Equipe Synthèse Organique & Méthodologie, Université Paris Sud, Bât. 420, 15 rue Georges Clémenceau, 91405 Orsay cedex, France. Electronic address: claire.grison@u-psud.fr.
authors: Claire M
authors: CM
authors: Grison
authors: CEFE UMR 5175, Campus CNRS, 1919 route de Mende, 34293 Montpellier cedex 5, France.
authors: Brice-Loïc
authors: BL
authors: Renard
authors: CEFE UMR 5175, Campus CNRS, 1919 route de Mende, 34293 Montpellier cedex 5, France.
authors: Claude
authors: C
authors: Grison
mesh_terms: D001419:Bacteria / Q000187:drug effects* / Q000235:genetics / Q000254:growth & development; D060326:Chemistry Techniques, Synthetic; D004275:DNA, Ribosomal; D004952:Esters / Q000138:chemical synthesis*; D007887:Fabaceae / Q000382:microbiology; D015394:Molecular Structure; D012988:Soil Microbiology; D013312:Stress, Physiological; D013400:Sugar Acids / Q000138:chemical synthesis* / Q000378:metabolism
chemical_list: C000590670:2-keto-3-deoxy-D-erythro-hexonic acid isopropyl ester; D004275:DNA, Ribosomal; D004952:Esters; D013400:Sugar Acids
keywords: 2-Keto-3-deoxy-D-erythro-hexonic acid isopropyl ester; Entner Doudoroff pathway; Heavy-metal resistant rhizobia; Modified Darzens reaction; One-pot isomerization-reduction reaction; Swern oxidation