title: Chemoenzymatic synthesis of CMP-N-acetyl-7-fluoro-7-deoxy-neuraminic acid.
abstract: 7-Fluoro sialic acid was prepared and activated as cytidine monophosphate (CMP) ester. The synthesis started with d-glucose, which was efficiently converted into N-acetyl-4-fluoro-4-deoxy-d-mannosamine. Aldolase catalyzed transformation yielded the corresponding fluorinated sialic acid which was activated as CMP ester using three different synthetases in the presence as well as in the absence of pyrophosphatase which possesses inhibitory properties. Finally, conditions were optimized to perform a one-pot reaction starting from fluorinated mannosamine, which yielded the 7-fluoro-7-deoxy-CMP-sialic acid by incubation with three enzymes.
authors: Institut für Organische Chemie und Zentrum für Biomolekulare Wirkstoffchemie (BMWZ), Gottfried Wilhelm Leibniz Universität Hannover, Schneiderberg 1B, 30167 Hannover, Germany.
authors: Sina
authors: S
authors: Hartlieb
authors: Almut
authors: A
authors: Günzel
authors: Rita
authors: R
authors: Gerardy-Schahn
authors: Anja K
authors: AK
authors: Münster-Kühnel
authors: Andreas
authors: A
authors: Kirschning
authors: Gerald
authors: G
authors: Dräger
mesh_terms: D003569:Cytidine Monophosphate N-Acetylneuraminic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D005634:Fructose-Bisphosphate Aldolase / Q000378:metabolism; D000216:N-Acylneuraminate Cytidylyltransferase / Q000378:metabolism
chemical_list: C532042:CMP-N-acetyl-7-fluoro-7-deoxyneuraminic acid; D003569:Cytidine Monophosphate N-Acetylneuraminic Acid; D000216:N-Acylneuraminate Cytidylyltransferase; D005634:Fructose-Bisphosphate Aldolase