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Originally published In Press as doi:10.1074/jbc.M101225200 on February 28, 2001

J. Biol. Chem., Vol. 276, Issue 22, 18765-18774, June 1, 2001
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Deoxysugar Methylation during Biosynthesis of the Antitumor Polyketide Elloramycin by Streptomyces olivaceus
CHARACTERIZATION OF THREE METHYLTRANSFERASE GENES*

Eugenio P. PatalloDagger , Gloria BlancoDagger , Carsten Fischer§, Alfredo F. BrañaDagger , Jürgen Rohr§, Carmen MéndezDagger , and José A. SalasDagger ||

From the Dagger  Departamento de Biología Funcional e Instituto Universitario de Oncología del Principado de Asturias, Universidad de Oviedo, 33006 Oviedo, Spain and § Medical University of South Carolina, Department of Pharmaceutical Sciences, Charleston, South Carolina 29425-2303

The anthracycline-like polyketide drug elloramycin is produced by Streptomyces olivaceus Tü2353. Elloramycin has antibacterial activity against Gram-positive bacteria and also exhibits antitumor activity. From a cosmid clone (cos16F4) containing part of the elloramycin biosynthesis gene cluster, three genes (elmMI, elmMII, and elmMIII) have been cloned. Sequence analysis and data base comparison showed that their deduced products resembled S-adenosylmethionine-dependent O-methyltransferases. The genes were individually expressed in Streptomyces albus and also coexpressed with genes involved in the biosynthesis of L-rhamnose, the 6-deoxysugar attached to the elloramycin aglycon. The resulting recombinant strains were used to biotransform three different elloramycin-type compounds: L-rhamnosyl-tetracenomycin C, L-olivosyl-tetracenomycin C, and L-oleandrosyl-tetracenomycin, which differ in their 2'-, 3'-, and 4'-substituents of the sugar moieties. When only the three methyltransferase-encoding genes elmMI, elmMII, and elmMIII were individually expressed in S. albus, the methylating activity of the three methyltransferases was also assayed in vitro using various externally added glycosylated substrates. From the combined results of all of these experiments, it is proposed that methyltransferases ElmMI, ElmMII, and ElmMIII are involved in the biosynthesis of the permethylated L-rhamnose moiety of elloramycin. ElmMI, ElmMII, and ElmMIII are responsible for the consecutive methylation of the hydroxy groups at the 2'-, 3'-, and 4'-position, respectively, after the sugar moiety has been attached to the aglycon.

* This work was supported by European Community Grant BIO4-CT96-0068 (to J. R. and J. A. S.), Spanish Ministry of Education and Science Grant BIO97-0771 through the "Plan Nacional en Biotecnologia" (to J. A. S.), and grants from the South Carolina Commission of Higher Education as well as the United States Department of Defense (to J. R.).The costs of publication of this article were defrayed in part by the payment of page charges. The article must therefore be hereby marked "advertisement" in accordance with 18 U.S.C. Section 1734 solely to indicate this fact.

The nucleotide sequence(s) reported in this paper has been submitted to the GenBankTM/EMBL Data Bank with accession number(s) AJ309821.

To whom correspondence should be addressed for chemical communications: Dept. of Pharmaceutical Sciences, Medical University of South Carolina, 171 Ashley Ave., Charleston, SC 29425-2303. Tel.: 843-953-6659; Fax: 843-953-6615; E-mail: rohrj@musc.edu.

|| To whom correspondence should be addressed for molecular biology communications: Dept. de Biología Funcional e Instituto Universitario de Oncología del Principado de Asturias, Universidad de Oviedo, 33006 Oviedo, Spain. Tel./Fax: 34-985-103652; E-mail: jasf@sauron. quimica.uniovi.es.

Copyright © 2001 by The American Society for Biochemistry and Molecular Biology, Inc.
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