ArticleJournal of the American Chemical Society2010
Biosynthesis of spinosyn in Saccharopolyspora spinosa: synthesis of permethylated rhamnose and characterization of the functions of SpnH, SpnI, and SpnK.
Article in Journal of the American Chemical Society, 2010. 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, 57 citations in OpenAlex.
- iCASRED, a scarless DNA editing tool inSynthetic and systems biotechnology · 2025Article
- Three distinct strategies lead to programmable aliphatic C-H oxidation in bicyclomycin biosynthesis.Nature communications · 2025Article
- Enhancement of spinosad production in Saccharopolyspora spinosa by overexpression of the complete 74-kb spinosyn gene cluster.Microbial cell factories · 2025Article
- Diversification of Ubiquinone Biosynthesis via Gene Duplications, Transfers, Losses, and Parallel Evolution.Molecular biology and evolution · 2023Article
- Endophytic actinobacteria from wild medicinal plants are a natural source of insecticide to control the African cotton leafworm (Spodoptera littoralis).AMB Express · 2023Article
- Engineering of flavonoid 3'-O-methyltransferase for improved biosynthesis of chrysoeriol in Escherichia coli.Applied microbiology and biotechnology · 2023Article
- Improving spinosad production by tuning expressions of the forosamine methyltransferase and the forosaminyl transferase to reduce undesired less active byproducts in the heterologous host Streptomyces albus J1074.Microbial cell factories · 2023Article
- Functional Characterization of a Regiospecific Sugar-Applied and environmental microbiology · 2022Article
- Increasing the heterologous production of spinosad inSynthetic and systems biotechnology · 2021Article
- Comparative transcriptomic analysis of two Saccharopolyspora spinosa strains reveals the relationships between primary metabolism and spinosad production.Scientific reports · 2021Article
- Genome mining of the sordarin biosynthetic gene cluster from Sordaria araneosa Cain ATCC 36386: characterization of cycloaraneosene synthase and GDP-6-deoxyaltrose transferase.The Journal of antibiotics · 2016Article
- Natural product derived insecticides: discovery and development of spinetoram.Journal of industrial microbiology & biotechnology · 2016Review
- Structural basis of substrate specificity and regiochemistry in the MycF/TylF family of sugar O-methyltransferases.ACS chemical biology · 2015Article
- Enzymatic methylation and structure-activity-relationship studies on polycarcin V, a gilvocarcin-type antitumor agent.Chembiochem : a European journal of chemical biology · 2014Article
- Chemoenzymatic synthesis of spinosyn A.Angewandte Chemie (International ed. in English) · 2014Article
- Metabolic engineering of rational screened Saccharopolyspora spinosa for the enhancement of spinosyns A and D production.Molecules and cells · 2014Article
- Draft Genome Sequence of Insecticidal Streptomyces sp. Strain PCS3-D2, Isolated from Mangrove Soil in Philippines.Genome announcements · 2014Article
- Genome-scale metabolic network reconstruction of Saccharopolyspora spinosa for spinosad production improvement.Microbial cell factories · 2014Article
- Differential proteomic profiling reveals regulatory proteins and novel links between primary metabolism and spinosad production in Saccharopolyspora spinosa.Microbial cell factories · 2014Article
- Structural and functional characterization of CalS11, a TDP-rhamnose 3'-O-methyltransferase involved in calicheamicin biosynthesis.ACS chemical biology · 2013Article
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Authors and funding
6 authors at 1 institution in 1 country.
Funding
Abstract
Spinosyn A is a polyketide-derived macrolide produced by Saccharopolyspora spinosa and is an active ingredient in several commercial insecticides. It is glycosylated by a tri-O-methylated rhamnose at C-9 and a forosamine at C-17. Previous studies indicated that the rhamnose methyltransferases are encoded by the spnH, spnI, and spnK genes. To verify the functions of these methyltransferases and to study how they are coordinated to achieve the desired level of methylation of rhamnose, we studied the catalytic properties of the spnH, spnI, and spnK gene products and validated their roles in the permethylation process of spinosyn A. Our data reported herein firmly established that SpnH, SpnI, and SpnK are the respective rhamnose 4'-, 2'-, and 3'-O-methyltransferase. Investigation of the order of the methylation events revealed that only one route catalyzed by SpnI, SpnK, and SpnH in sequence is productive for the permethylation of the rhamnose moiety. Moreover, the completion of rhamnose permethylation is likely achieved by the proper control of the expression levels of the methyltransferase genes involved. These results set the stage for future exploitation of the spinosyn biosynthetic pathway to produce targeted spinosyn derivatives and, perhaps, new analogues.
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