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

W.B. Turnbull; J.A. Harrison; K.P. Ravindranathan Kartha; S. Schenkman; R.A. Field

doi:10.1016/S0040-4020(02)00265-X

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

W.B. Turnbull, J.A. Harrison, K.P. Ravindranathan Kartha, S. Schenkman, R.A. Field

Manchester Institute of Biotechnology

Research output: Contribution to journal › Article › peer-review

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 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.

Coupling efficiency and stereoselectivity in the α-2,3-sialylation of octyl lactoside have been compared.

Original language	Undefined
Pages (from-to)	3207-3216
Number of pages	10
Journal	Tetrahedron
Volume	58
Issue number	16
DOIs	https://doi.org/10.1016/S0040-4020(02)00265-X
Publication status	Published - 15 Apr 2002

Keywords

trans-sialidase
synthesis
biotransformations

Research Beacons, Institutes and Platforms

Manchester Institute of Biotechnology

Access to Document

10.1016/S0040-4020(02)00265-X

Cite this

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AU - Turnbull, W.B.

AU - Harrison, J.A.

AU - Ravindranathan Kartha, K.P.

AU - Schenkman, S.

AU - Field, R.A.

PY - 2002/4/15

Y1 - 2002/4/15

N2 - 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 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.Coupling efficiency and stereoselectivity in the α-2,3-sialylation of octyl lactoside have been compared.

AB - 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 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.Coupling efficiency and stereoselectivity in the α-2,3-sialylation of octyl lactoside have been compared.

KW - trans-sialidase

KW - synthesis

KW - biotransformations

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DO - 10.1016/S0040-4020(02)00265-X

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EP - 3216

JO - Tetrahedron

JF - Tetrahedron

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

Abstract

Keywords

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