Novel desosaminyl derivatives of dihydrochalcomycin from a genetically engineered strain of Streptomyces sp.
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.
Pageni
Binod Babu
BB
Institute of Biomolecule Reconstruction, Department of Pharmaceutical Engineering, SunMoon University, #100, Kalsan-ri, Tangjeong-myeon, Asansi, Chungnam, 336-708, Korea.
Oh
Tae-Jin
TJ
Sohng
Jae Kyung
JK
D000606:Amino Sugars / Q000737:chemistry* / Q000378:metabolism; D002853:Chromatography, Liquid; D019295:Computational Biology; D020868:Gene Silencing; D005798:Genes, Bacterial; D005818:Genetic Engineering; D006031:Glycosylation; D018942:Macrolides / Q000737:chemistry / Q000302:isolation & purification*; D013058:Mass Spectrometry; D009702:Nucleoside Diphosphate Sugars; D013302:Streptomyces / Q000235:genetics*; D013942:Thymine Nucleotides / Q000378:metabolism
D000606:Amino Sugars; D018942:Macrolides; D009702:Nucleoside Diphosphate Sugars; C513911:TDP-D-desosamine; D013942:Thymine Nucleotides; C110125:desosamine; C002018:chalcomycin