Observations on chemical and enzymatic approaches to α-2, 3-sialylated octyl β-lactoside

WB Turnbull, JA Harrison, KPR Kartha, S Schenkman…

Index: Turnbull, W.Bruce; Harrison, Jennifer A; Ravindranathan Kartha; Schenkman, Sergio; Field, Robert A Tetrahedron, 2002 , vol. 58, # 16 p. 3207 - 3216

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Citation Number: 23

Abstract

A comparison of chemical and chemo-enzymatic syntheses of α-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 α-selectivity in the sialylation step necessitated a difficult and low yielding separation of anomers. A chemoenzymatic approach, employing recombinant Trypanosoma cruzitrans-sialidase to effect the key ...