Observations on chemical and enzymatic approaches to alpha-2,3-sialylated octyl beta-lactoside
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2002-04-15
Autores
Turnbull, W. B.
Harrison, J. A.
Kartha, KPR
Schenkman, S.
Field, R. A.
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A comparison of chemical and chemo-enzymatic syntheses of alpha-2,3-sialylated octyl lactoside is reported. the chemical approach, starting from lactose and sialic acid, required 14 steps and proceeded in 5% overall yield; poor a-selectivity in the sialylation step necessitated a difficult and low yielding separation of anomers. A chemoenzymatic approach, employing recombinant Trypanosoma cruzi trans-sialidase to effect the key sialylation reaction, required 10 steps and gave a similar overall yield. Whereas the chemo-enzymatic synthesis required only three chromatographic purification steps overall, the chemical synthesis required at least nine. (C) 2002 Elsevier B.V. All rights reserved.
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Tetrahedron. Oxford: Pergamon-Elsevier B.V., v. 58, n. 16, p. 3207-3216, 2002.