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

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dc.contributor.author Turnbull, W. B.
dc.contributor.author Harrison, J. A.
dc.contributor.author Kartha, KPR
dc.contributor.author Schenkman, S.
dc.contributor.author Field, R. A.
dc.date.accessioned 2016-01-24T12:33:21Z
dc.date.available 2016-01-24T12:33:21Z
dc.date.issued 2002-04-15
dc.identifier http://dx.doi.org/10.1016/S0040-4020(02)00265-X
dc.identifier.citation Tetrahedron. Oxford: Pergamon-Elsevier B.V., v. 58, n. 16, p. 3207-3216, 2002.
dc.identifier.issn 0040-4020
dc.identifier.uri http://repositorio.unifesp.br/handle/11600/26833
dc.description.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. en
dc.format.extent 3207-3216
dc.language.iso eng
dc.publisher Elsevier B.V.
dc.relation.ispartof Tetrahedron
dc.rights Acesso restrito
dc.subject trans-sialidase en
dc.subject synthesis en
dc.subject biotransformations en
dc.title Observations on chemical and enzymatic approaches to alpha-2,3-sialylated octyl beta-lactoside en
dc.type Artigo
dc.rights.license http://www.elsevier.com/about/open-access/open-access-policies/article-posting-policy
dc.contributor.institution Univ St Andrews
dc.contributor.institution Universidade Federal de São Paulo (UNIFESP)
dc.description.affiliation Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland
dc.description.affiliation Univ St Andrews, Ctr Biomol Sci, St Andrews KY16 9ST, Fife, Scotland
dc.description.affiliation Escola Paulista Med, Disciplina Biol Celular, BR-04023062 São Paulo, Brazil
dc.description.affiliationUnifesp Escola Paulista Med, Disciplina Biol Celular, BR-04023062 São Paulo, Brazil
dc.identifier.doi 10.1016/S0040-4020(02)00265-X
dc.description.source Web of Science
dc.identifier.wos WOS:000175933700011



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