Issue 1, 1994

New synthetic applications of sialic acid aldolase, a useful catalyst for KDO synthesis. Relation between substrate conformation and enzyme stereoselectivity

Abstract

In the sialic acid aldolase-catalysed addition of pyruvate with D-arabinose leading to a mixture of 3-deoxy-D-manno-oct-2-ulosonic acid (KDO) and 4-epi-KDO (both in pyranose and furanose form), a high concentration of the acceptor D-arabinose have been found to increase the percentage of KDO up to 83%. KDO synthesis scaled up in the enzyme membrane reactor is reported. New condensation products obtained from L-xylose, L-allose, D-altrose and D-ribose as substrates are described as well. Kinetic parameters for the cleavage of KDO and 4-epi-KDO and the addition reaction between pyruvate and xylose and arabinose are given. Some apparent relation between enzyme stereoselectivity and conformation and stereochemistry at carbon C-3 of the substrate is discussed.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1994, 119-124

New synthetic applications of sialic acid aldolase, a useful catalyst for KDO synthesis. Relation between substrate conformation and enzyme stereoselectivity

U. Kragl, A. Gödde, C. Wandrey, N. Lubin and C. Augé, J. Chem. Soc., Perkin Trans. 1, 1994, 119 DOI: 10.1039/P19940000119

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