Lipophilic sugar nucleotide synthesis by structure-based design of nucleotidylyltransferase substrates (original) (raw)

* Corresponding authors

a College of Pharmacy, Burbidge Building, Dalhousie University, 5968 College St., Halifax, Nova Scotia, Canada
E-mail: david.jakeman@dal.ca
Fax: 1 902 494 1396
Tel: 1 902 494 7159

b MS Metabolomics Group, NRC-Institute for Marine Biosciences, 1411 Oxford Street, Halifax, Nova Scotia, Canada
E-mail: evelyn.soo@nrc-cnrc.gc.ca

c Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, Canada

Abstract

Structure-based design of alkyl sugar-1-phosphates provides an efficient nucleotidylyltransferase-catalyzed synthesis of a series of new lipophilic sugar nucleotides possessing long or branched alkyl chains, thereby demonstrating the utility of nucleotidylyltransferases to catalyze the synthesis of sugar nucleotides with potential applications in lipopolysaccharide and lipoglycopeptide biosynthesis.

Graphical abstract: Lipophilic sugar nucleotide synthesis by structure-based design of nucleotidylyltransferase substrates

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Supplementary files

Experimental procedures and NMR data for compounds 2b–h to 8a–h, NMR spectra for compounds 6a–h and 8a–h. Details describing enzymatic assays, HPLC and ESI/MS/MS data for sugar nucleotides (94 pages) PDF (7551K)

Article information

DOI

https://doi.org/10.1039/B716955H

Article type

Paper

Submitted

02 Nov 2007

Accepted

22 Nov 2007

First published

11 Dec 2007

Download Citation

Org. Biomol. Chem., 2008,6, 477-484

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