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

Autor Turnbull, W. B. Google Scholar
Harrison, J. A. Google Scholar
Kartha, KPR Google Scholar
Schenkman, S. Google Scholar
Field, R. A. Google Scholar
Instituição Univ St Andrews
Universidade Federal de São Paulo (UNIFESP)
Resumo 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.
Palavra-chave trans-sialidase
synthesis
biotransformations
Idioma Inglês
Data de publicação 2002-04-15
Publicado em Tetrahedron. Oxford: Pergamon-Elsevier B.V., v. 58, n. 16, p. 3207-3216, 2002.
ISSN 0040-4020 (Sherpa/Romeo, fator de impacto)
Publicador Elsevier B.V.
Extensão 3207-3216
Fonte http://dx.doi.org/10.1016/S0040-4020(02)00265-X
Direito de acesso Acesso restrito
Tipo Artigo
Web of Science WOS:000175933700011
Endereço permanente http://repositorio.unifesp.br/handle/11600/26833

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