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J. Biol. Chem., Vol. 280, Issue 37, 32493-32498, September 16, 2005

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Structure and Biosynthesis of Staphyloxanthin from Staphylococcus aureus^*

Alexandra Pelz, Karsten-Peter Wieland, Karsten Putzbach, Petra Hentschel, Klaus Albert, and Friedrich Götz1

From the Department of Microbial Genetics and the Institute of Organic Chemistry, University of Tuebingen, D-72076 Tuebingen, Germany

Most Staphylococcus aureus strains produce the orange carotenoid staphyloxanthin. The staphyloxanthin biosynthesis genes are organized in an operon, crtOPQMN, with a ^B-dependent promoter upstream of crtO and a termination region downstream of crtN. The functions of the five encoded enzymes were predicted on the basis of their sequence similarity to known enzymes and by product analysis of gene deletion mutants. The first step in staphyloxanthin biosynthesis is the head-to-head condensation of two molecules of farnesyl diphosphate to form dehydrosqualene (4,4'-diapophytoene), catalyzed by the dehydrosqualene synthase CrtM. The dehydrosqualene desaturase CrtN dehydrogenates dehydrosqualene to form the yellow, main intermediate 4,4'-diaponeurosporene. CrtP, very likely a mixed function oxidase, oxidizes the terminal methyl group of 4,4'-diaponeurosporene to form 4,4'-diaponeurosporenic acid. CrtQ, a glycosyltransferase, esterifies glucose at the C₁'' position with the carboxyl group of 4,4'-diaponeurosporenic acid to yield glycosyl 4,4'-diaponeurosporenoate; this compound was the major product in the clone expressing crtPQMN. In the final step, the acyltransferase CrtO esterifies glucose at the C₆'' position with the carboxyl group of 12-methyltetradecanoic acid to yield staphyloxanthin. Staphyloxanthin overexpressed in Staphylococcus carnosus (pTX-crtOPQMN) and purified was analyzed by high pressure liquid chromatography-mass spectroscopy and NMR spectroscopy. Staphyloxanthin was identified as -D-glucopyranosyl 1-O-(4,4'-diaponeurosporen-4-oate)-6-O-(12-methyltetradecanoate).

Received for publication, May 9, 2005 , and in revised form, July 11, 2005.

The nucleotide sequence(s) reported in this paper has been submitted to the GenBank^TM/EBI Data Bank with accession number(s) X97985.

^* This work was supported by grants from the Deutsche Forschungsgemeinschaft: FOR 449/1, the Graduate College 685, BMBF Kompetenznetz PathoGenoMik (031U213B), the DFG-Forschergruppe (G0 371/5-3/4), and the graduate college "infection biology" (IIIGK-GRK 685/2-04). The costs of publication of this article were defrayed in part by the payment of page charges. This article must therefore be hereby marked "advertisement" in accordance with 18 U.S.C. Section 1734 solely to indicate this fact.

¹ To whom correspondence should be addressed: Dept. of Microbial Genetics, University of Tuebingen, Waldhauser Str. 70/8, D-72076 Tuebingen, Germany. Tel.: 49-7071-2974636; Fax: 49-7071-2975937; E-mail: friedrich.goetz{at}uni-tuebingen.de.

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