ArticleApplied and environmental microbiology2006
Deoxysugar transfer during chromomycin A3 biosynthesis in Streptomyces griseus subsp. griseus: new derivatives with antitumor activity.
Article in Applied and environmental microbiology, 2006. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.
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Who cites it
24 citing papers in PubMed, 54 citations in OpenAlex.
- Genome Mining for Diazo-Synthesis-Related Genes inBiomolecules · 2024Article
- Engineering BioBricks for Deoxysugar Biosynthesis and Generation of New Tetracenomycins.ACS omega · 2023Article
- Uncovering the Cryptic Gene ClusterInternational journal of molecular sciences · 2023Article
- Biosynthesis of Largimycins inACS chemical biology · 2022Article
- Heterologous reconstitution of the biosynthesis pathway for 4-demethyl-premithramycinone, the aglycon of antitumor polyketide mithramycin.Microbial cell factories · 2020Article
- New Sipanmycin Analogues Generated by Combinatorial Biosynthesis and Mutasynthesis Approaches Relying on the Substrate Flexibility of Key Enzymes in the Biosynthetic Pathway.Applied and environmental microbiology · 2020Article
- Article
- Searching for Glycosylated Natural Products in Actinomycetes and Identification of Novel Macrolactams and Angucyclines.Frontiers in microbiology · 2018Article
- Caboxamycin biosynthesis pathway and identification of novel benzoxazoles produced by cross-talk in Streptomyces sp. NTK 937.Microbial biotechnology · 2017Article
- Reductive Deamination by Benzyne for Deoxy Sugar Synthesis Through a Domino Reaction.ChemistryOpen · 2017Article
- Exploring the biocombinatorial potential of benzoxazoles: generation of novel caboxamycin derivatives.Microbial cell factories · 2017Article
- Identification by Genome Mining of a Type I Polyketide Gene Cluster fromFrontiers in microbiology · 2017Article
- New insights into paulomycin biosynthesis pathway in Streptomyces albus J1074 and generation of novel derivatives by combinatorial biosynthesis.Microbial cell factories · 2016Article
- Structural insight into MtmC, a bifunctional ketoreductase-methyltransferase involved in the assembly of the mithramycin trisaccharide chain.Biochemistry · 2015Article
- Chromomycin A2 induces autophagy in melanoma cells.Marine drugs · 2014Article
- Activation and identification of five clusters for secondary metabolites in Streptomyces albus J1074.Microbial biotechnology · 2014Article
- Participation of putative glycoside hydrolases SlgC1 and SlgC2 in the biosynthesis of streptolydigin in Streptomyces lydicus.Microbial biotechnology · 2012Article
- Amino acid precursor supply in the biosynthesis of the RNA polymerase inhibitor streptolydigin by Streptomyces lydicus.Journal of bacteriology · 2011Article
- Biosynthesis of the RNA polymerase inhibitor streptolydigin in Streptomyces lydicus: tailoring modification of 3-methyl-aspartate.Journal of bacteriology · 2011Article
- Molecular insights on the biosynthesis of antitumour compounds by actinomycetes.Microbial biotechnology · 2011Review
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Authors and funding
7 authors at 2 institutions in 2 countries.
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Abstract
Chromomycin A3 is an antitumor drug produced by Streptomyces griseus subsp. griseus. It consists of a tricyclic aglycone with two aliphatic side chains and two O-glycosidically linked saccharide chains, a disaccharide of 4-O-acetyl-D-oliose (sugar A) and 4-O-methyl-D-oliose (sugar B), and a trisaccharide of D-olivose (sugar C), D-olivose (sugar D), and 4-O-acetyl-L-chromose B (sugar E). The chromomycin gene cluster contains four glycosyltransferase genes (cmmGI, cmmGII, cmmGIII, and cmmGIV), which were independently inactivated through gene replacement, generating mutants C60GI, C10GII, C10GIII, and C10GIV. Mutants C10GIV and C10GIII produced the known compounds premithramycinone and premithramycin A1, respectively, indicating the involvement of CmmGIV and CmmGIII in the sequential transfer of sugars C and D and possibly also of sugar E of the trisaccharide chain, to the 12a position of the tetracyclic intermediate premithramycinone. Mutant C10GII produced two new tetracyclic compounds lacking the disaccharide chain at the 8 position, named prechromomycin A3 and prechromomycin A2. All three compounds accumulated by mutant C60GI were tricyclic and lacked sugar B of the disaccharide chain, and they were named prechromomycin A4, 4A-O-deacetyl-3A-O-acetyl-prechromomycin A4, and 3A-O-acetyl-prechromomycin A4. CmmGII and CmmGI are therefore responsible for the formation of the disaccharide chain by incorporating, in a sequential manner, two D-oliosyl residues to the 8 position of the biosynthetic intermediate prechromomycin A3. A biosynthetic pathway is proposed for the glycosylation events in chromomycin A3 biosynthesis.
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