Observations on chemical and enzymatic approaches to alpha-2,3-sialylated octyl beta-lactoside

Observations on chemical and enzymatic approaches to alpha-2,3-sialylated octyl beta-lactoside

Author Turnbull, W. B. Google Scholar
Harrison, J. A. Google Scholar
Kartha, KPR Google Scholar
Schenkman, S. Google Scholar
Field, R. A. Google Scholar
Institution Univ St Andrews
Universidade Federal de São Paulo (UNIFESP)
Abstract 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.
Keywords trans-sialidase
synthesis
biotransformations
Language English
Date 2002-04-15
Published in Tetrahedron. Oxford: Pergamon-Elsevier B.V., v. 58, n. 16, p. 3207-3216, 2002.
ISSN 0040-4020 (Sherpa/Romeo, impact factor)
Publisher Elsevier B.V.
Extent 3207-3216
Origin http://dx.doi.org/10.1016/S0040-4020(02)00265-X
Access rights Closed access
Type Article
Web of Science ID WOS:000175933700011
URI http://repositorio.unifesp.br/handle/11600/26833

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