ArticleJournal of the American Chemical Society2012
Construction of the octose 8-phosphate intermediate in lincomycin A biosynthesis: characterization of the reactions catalyzed by LmbR and LmbN.
Article in Journal of the American Chemical Society, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed, 43 citations in OpenAlex.
- Structure-Guided Mechanistic Investigation of Stereochemical Inversion during the Octose Formation Catalyzed by an Atypical Transaldolase AprG in the Biosynthesis of Apramycin.ACS catalysis · 2025Article
- Biosynthetic Origin of the Octose Core and Its Mechanism of Assembly during Apramycin Biosynthesis.Journal of the American Chemical Society · 2023Article
- Characterization and utilization of methyltransferase for apramycin production in Streptoalloteichus tenebrarius.Journal of industrial microbiology & biotechnology · 2022Article
- Drug Repurposing: A Review of Old and New Antibiotics for the Treatment of Malaria: Identifying Antibiotics with a Fast Onset of Antiplasmodial Action.Molecules (Basel, Switzerland) · 2021Review
- Studies of lincosamide formation complete the biosynthetic pathway for lincomycin A.Proceedings of the National Academy of Sciences of the United States of America · 2020Article
- Synthesis of Gentamicin Minor Components: Gentamicin B1 and Gentamicin X2.Organic letters · 2020Article
- Comparative transcriptomic analysis reveals the significant pleiotropic regulatory effects of LmbU on lincomycin biosynthesis.Microbial cell factories · 2020Article
- AdpAFrontiers in microbiology · 2019Article
- The Novel Transcriptional Regulator LmbU Promotes Lincomycin Biosynthesis through Regulating Expression of Its Target Genes in Streptomyces lincolnensis.Journal of bacteriology · 2018Article
- Octulose: a forgotten metabolite?Journal of experimental botany · 2017Review
- Elucidation of salicylate attachment in celesticetin biosynthesis opens the door to create a library of more efficient hybrid lincosamide antibiotics.Chemical science · 2017Article
- Characterization of Enzymes Catalyzing Transformations of Cysteine S-Conjugated Intermediates in the Lincosamide Biosynthetic Pathway.Chembiochem : a European journal of chemical biology · 2016Article
- New Concept of the Biosynthesis of 4-Alkyl-L-Proline Precursors of Lincomycin, Hormaomycin, and Pyrrolobenzodiazepines: Could a γ-Glutamyltransferase Cleave the C-C Bond?Frontiers in microbiology · 2016Article
- Deacetylation of mycothiol-derived 'waste product' triggers the last biosynthetic steps of lincosamide antibiotics.Chemical science · 2016Article
- Biochemistry: Elusive source of sulfur unravelled.Nature · 2015Article
- Metabolic coupling of two small-molecule thiols programs the biosynthesis of lincomycin A.Nature · 2015Article
- Lincosamide synthetase--a unique condensation system combining elements of nonribosomal peptide synthetase and mycothiol metabolism.PloS one · 2015Article
- In vitro characterization of LmbK and LmbO: identification of GDP-D-erythro-α-D-gluco-octose as a key intermediate in lincomycin A biosynthesis.Journal of the American Chemical Society · 2014Article
- The biosynthesis of nitrogen-, sulfur-, and high-carbon chain-containing sugars.Chemical Society reviews · 2013Review
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
Lincomycin A is a potent antimicrobial agent noted for its unusual C1 methylmercapto-substituted 8-carbon sugar. Despite its long clinical history for the treatment of Gram-positive infections, the biosynthesis of the C(8)-sugar, methylthiolincosamide (MTL), is poorly understood. Here, we report our studies of the two initial enzymatic steps in the MTL biosynthetic pathway leading to the identification of D-erythro-D-gluco-octose 8-phosphate as a key intermediate. Our experiments demonstrate that this intermediate is formed via a transaldol reaction catalyzed by LmbR using D-fructose 6-phosphate or D-sedoheptulose 7-phosphate as the C(3) donor and D-ribose 5-phosphate as the C(5) acceptor. Subsequent 1,2-isomerization catalyzed by LmbN converts the resulting 2-keto C(8)-sugar (octulose 8-phosphate) to octose 8-phosphate. These results provide, for the first time, in vitro evidence for the biosynthetic origin of the C(8) backbone of MTL.
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