Novel desosaminyl derivatives of dihydrochalcomycin from a genetically engineered strain of Streptomyces sp.

Binod Babu Pageni, Tae-Jin Oh, Jae Kyung Sohng

Institute of Biomolecule Reconstruction, Department of Pharmaceutical Engineering, SunMoon University, #100, Kalsan-ri, Tangjeong-myeon, Asansi, Chungnam, 336-708, Korea.

Biotechnology letters 2009 Nov

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Dihydrochalcomycin from Streptomyces sp. KCTC 0041BP is a 16-membered macrolide antibiotic containing two deoxysugars (D-chalcose and D-mycinose) that are O-glycosylated at the C-5 and C-20 positions, respectively. The desosamine sugar cassette was constructed from pikromycin-deoxysugar biosynthetic genes and transformed into Streptomyces sp. GerSM1, which was engineered for deletion of the genes related to TDP-D-chalcose biosynthesis (gerB, gerN and gerMI). Novel 16-membered macrolides (5-O-desosaminyl derivatives of dihydrochalcomycin) were detected by ESI-MS, LC/MS, and MS/MS thereby demonstrating combinatorial biosynthesis of the deoxysugar in 16-membered macrolide antibiotics.

Citation

Binod Babu Pageni, Tae-Jin Oh, Jae Kyung Sohng. Novel desosaminyl derivatives of dihydrochalcomycin from a genetically engineered strain of Streptomyces sp. Biotechnology letters. 2009 Nov;31(11):1759-68