✍ Scribed by Jacquelyn Gervay; Travis Q. Gregar
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Peracetylated ester derivatives of N-acetyl neuraminic acid were reacted with hydrogen iodide in acetic acid to stereoselectively provide a-2-deoxy-2-hydrido analogs. The reaction proceeds through formation of an anomeric iodide which, in the presence of excess HI, is reduced to give an enol intermediate. Kinetic protonation of the intermediam enol gives a 3.4:1 m13 mixture of 2-deoxy-2-hydrido derivatives. Under thermodynamic conditions the a-anomer is formed exclusively. © 1997 Elsevier Science Ltd.
N-Acetyl neuraminic acid (NeuAc) is an important cellular component involved in numerous biological processes. Derivatives of NeuAc have been targeted as inhibitors of important metabolic enzymes including neuraminidas~, CMP-sythetases, and hemaggiutinins of the influenza virus. 2 NeuAc is most often presented to these enzymes as an c~-linked giycolipid conjugate with tim carboxylate occupying the axial position, however these arc not always necessary requirements for inhibitor activity. For example, the equatorial 2-deoxy-2-hydrido derivative 1 is an inhibitor of X-31 HA hemagglutinin, 3 and the axial derivative 2 is an inhibitor of Vibio cholerae sialidas¢. 4 Because NeuAc is a 3-deoxy sugar,
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