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M109377200v1
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Papers In Press, published online ahead of print November 8, 2001
J. Biol. Chem, 10.1074/jbc.M109377200
Submitted on September 27, 2001
Revised on November 8, 2001
Accepted on November 8, 2001

Oxidative Decarboxylation of UDP-Glucuronic Acid in Extracts of Polymyxin Resistant Escherichia coli. Origin of lipid A species modified with 4-amino-4-deoxy-L-arabinose

Steven D. Breazeale, Anthony A. Ribeiro, and Christian R. H. Raetz

Biochemistry, Duke University Medical Center, Durham, NC 27710

Corresponding Author: Raetz{at}biochem.duke.edu

Addition of the 4-amino-4-deoxy-L-arabinose (L-Ara4N) moiety to the phosphate groups of lipid A is implicated in bacterial resistance to polymyxin and cationic anti-microbial peptides of the innate immune system. The sequences of the products of the Salmonella typhimurium pmrE and pmrF loci, both of which are required for polymyxin resistance, recently led us to propose a pathway for L-Ara4N biosynthesis from UDP-glucuronic acid (Zhou et al. J. Biol. Chem. 274, 18503-18514, 1999). We now report that extracts of a polymyxin resistant mutant of E. coli catalyze the C-4" oxidation and C-6" decarboxylation of [32P]UDP-glucuronic acid, followed by transamination to generate [32P]UDP-L-Ara4N, when NAD and glutamate are added as co-substrates. In addition, the [32P]UDP-L-Ara4N is formylated when N-10-formyltetrahydrofolate is included. These activities are consistent with the proposed functions of two of the gene products (PmrI and PmrH) of the pmrF operon. PmrI (renamed ArnA) was over-expressed using a T7 construct, and shown by itself to catalyze the unprecedented oxidative decarboxylation of UDP-glucuronic acid to form uridine 5'-(ß-L-threo-pentapyranosyl-4"-ulose diphosphate). A 6 mg sample of the latter was purified, and its structure was validated by NMR studies as the hydrate of the 4" ketone. ArnA resembles UDP-galactose epimerase, dTDP-glucose-4,6-dehydratase, and UDP-xylose synthase in oxidizing the C-4" position of its substrate, but differs in that it releases the NADH product.


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