Synthesis of 3-deoxy-D-manno-2-octulosonic acid (KDO) and its analogs based on KDO aldolase-catalyzed reactions

作者: Takeshi Sugai , Gwo Jenn Shen , Yoshitaka Ichikawa , Chi Huey Wong

DOI: 10.1021/JA00055A008

关键词: SubstituentAldol condensationStereochemistryEnzymeChemistryYield (chemistry)Aldolase AReaction mechanismAldol reactionCatalysis

摘要: 3-Deoxy-D-manno-2-octulosonic acid (D-KDO) was synthesized from D-arabinose and pyruvate in 67% yield by using KDO aldolase (EC 4.1.2.21) Aureobacterium barkerei strain KDO-37-2 (ATCC 49977). Studies on the substrate specificity of enzyme with more than 20 natural unnatural sugars indicate that this widely accepts trioses, tetroses, pentoses, hexoses as substrates, especially ones R configuration at 1 position. The substituent 2 position had little effect aldol reaction

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