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The synthesis and enzymatic incorporation of sialic acid derivatives for use as tools to study the structure, activity, and inhibition of glycoproteins and other glycoconjugates

1998; Elsevier BV; Volume: 6; Issue: 8 Linguagem: Inglês

10.1016/s0968-0896(98)00121-7

1464-3391

Richard Martin, Krista Witte, Chi‐Huey Wong,

Biochemical and Molecular Research

Methods have been developed for the enzymatic synthesis of complex carbohydrates and glycoproteins containing in the sialic acid moiety the heavy metal mercury or the transition-state analog phosphonate of the influenza C 9-O-acetyl-neuraminic acid esterase-catalyzed reaction. 5-Acetamido-3,5-dideoxy-9-methylphosphono-β-d-glycero-d-galacto-nonulopyranosidonic acid (1), 5-acetamido-3,5-dideoxy-9-methylphosphono-2-propyl-α-d-glycero-d-galacto-nonulopyranosidonic acid triethylammonium salt (2), and 5-acetamido-9-thiomethylmercuric-3,5,9-trideoxy-β-d-glycero-d-galacto-nonulopyranosidonic acid (3) were synthesized. Compounds 1 and 2 are proposed transition state inhibitors of an esterase vital for the binding and infection of influenza C. Compound 3 was enzymatically incorporated into an oligosaccharide and a non-natural glycoprotein for use as an aid in the structure determination of these compounds by X-ray crystallography.