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Applied and Environmental Microbiology, May 2002, p. 2404-2410, Vol. 68, No. 5
0099-2240/02/$04.00+0     DOI: 10.1128/AEM.68.5.2404-2410.2002
Copyright © 2002, American Society for Microbiology. All Rights Reserved.

Enzymatic Synthesis of Aminoglycoside Antibiotics: Novel Adenosylmethionine:2-Deoxystreptamine N-Methyltransferase Activities in Hygromycin B- and Spectinomycin-Producing Streptomyces spp. and Uses of the Methylated Products

James B. Walker*

Department of Biochemistry and Cell Biology, Rice University, Houston, Texas 77251

Received 11 December 2001/ Accepted 26 February 2002

Aminocyclitols structurally related to streptamine, a 1,3-diaminocyclitol, are common components of the RNA-binding aminoglycoside antibiotics. The respective aminocyclitol cores of hygromycin B and spectinomycin are N3-methyl-2-deoxy-D-streptamine and N1,N3-dimethyl-2-epi-streptamine. Adenosyl[methyl-14C]methionine:2-deoxystreptamine N-methyltransferase activities were detected in extracts of early-stationary-phase mycelia of the hygromycin B producer Streptomyces hygroscopicus subsp. hygroscopicus ATCC 27438 and the spectinomycin producer Streptomyces flavopersicus ATCC 19756. Extracts of both strains methylated the N1- and N3-amino groups of 2-deoxystreptamine, streptamine, and 2-epi-streptamine; the N1-amino group of N3-methyl-2-deoxy-D-streptamine, and the N3-amino group of N1-ethyl-2-deoxy-D-streptamine, the semisynthetic aminocyclitol of netilmicin. The mono[14C]methyl derivatives of 2-deoxystreptamine, streptamine, and 2-epi-streptamine were excellent substrates for L-glutamine:aminocyclitol aminotransferase and thereby provided a sensitive assay for derepression of this key enzyme, a generic biosynthetic marker that we have shown to be the only enzyme common to the biosyntheses of all major aminoglycoside antibiotics. Other prospective uses for these methyl-labeled 2-deoxystreptamine analogs are also described.

* Mailing address: Department of Biochemistry and Cell Biology, MS 140, Rice University, P.O. Box 1892, Houston, TX 77251-1892. Phone: (713) 348-4015. Fax: (713) 348-5154. E-mail: bioc{at}rice.edu.

Applied and Environmental Microbiology, May 2002, p. 2404-2410, Vol. 68, No. 5
0099-2240/02/$04.00+0     DOI: 10.1128/AEM.68.5.2404-2410.2002
Copyright © 2002, American Society for Microbiology. All Rights Reserved.





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