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

Turnbull, W. Bruce, Harrison, Jennifer A., Kartha, K. P. Ravindranathan, Schenkman, Sergio and Field, Robert A. ORCID: https://orcid.org/0000-0001-8574-0275 (2002) Observations on chemical and enzymatic approaches to α-2,3-sialylated octyl β-lactoside. Tetrahedron, 58 (16). pp. 3207-3216. ISSN 0040-4020

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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.

Item Type:	Article
Additional Information:	Funding Information: This project was supported by project grants from the Wellcome Trust and the MRC; studentship support from the AICR (W. B. T.) and BBSRC (J. A. H.) is also gratefully acknowledged.
Uncontrolled Keywords:	biotransformations,synthesis,trans-sialidase,biochemistry,drug discovery,organic chemistry ,/dk/atira/pure/subjectarea/asjc/1300/1303
Faculty \ School:	Faculty of Science > School of Chemistry, Pharmacy and Pharmacology
Related URLs:	http://www.scopus.com/inward/record.url?...
Depositing User:	LivePure Connector
Date Deposited:	10 Sep 2024 12:30
Last Modified:	25 Sep 2024 18:08
URI:	https://ueaeprints.uea.ac.uk/id/eprint/96659
DOI:	10.1016/S0040-4020(02)00265-X

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