ArticleMolecules (Basel, Switzerland)2016
A Chemo-Enzymatic Road Map to the Synthesis of CoA Esters.
Article in Molecules (Basel, Switzerland), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 40 papers.
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Who cites it
40 citing papers in PubMed, 82 citations in OpenAlex.
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- Non-modular fatty acid synthases yield distinct N-terminal acylation in ribosomal peptides.Nature chemistry · 2024Article
- Revealing reaction intermediates in one-carbon elongation by thiamine diphosphate/CoA-dependent enzyme family.Communications chemistry · 2024Article
- From waste to health-supporting molecules: biosynthesis of natural products from lignin-, plastic- and seaweed-based monomers using metabolically engineered Streptomyces lividans.Microbial cell factories · 2023Article
- Current State-of-the-Art Toward Chemoenzymatic Synthesis of Polyketide Natural Products.Chembiochem : a European journal of chemical biology · 2023Review
- Advances in direct detection of lysine methylation and acetylation by nuclear magnetic resonance usingMethods (San Diego, Calif.) · 2023Article
- Functional Degeneracy in Paracoccus denitrificans Pd1222 Is Coordinated via RamB, Which Links Expression of the Glyoxylate Cycle to Activity of the Ethylmalonyl-CoA Pathway.Applied and environmental microbiology · 2023Article
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- Enhancing the Substrate Specificity ofBiochemistry · 2023Article
- Structural Basis for a Cork-Up Mechanism of the Intra-Molecular Mesaconyl-CoA Transferase.Biochemistry · 2023Article
- Thioester and Oxyester Linkages in the Ubiquitin System.Methods in molecular biology (Clifton, N.J.) · 2023Review
- Time-resolved multiparameter analytics on a cell-free production platform for acyl-CoA precursors.Analytical science advances · 2022Article
- Chemical Synthesis ofMolecules (Basel, Switzerland) · 2022Article
- Bacterial Hydratases Involved in Steroid Side Chain Degradation Have Distinct Substrate Specificities.Journal of bacteriology · 2022Article
Corrections and comments
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Authors and funding
4 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Coenzyme A (CoA) is a ubiquitous cofactor present in every known organism. The thioesters of CoA are core intermediates in many metabolic processes, such as the citric acid cycle, fatty acid biosynthesis and secondary metabolism, including polyketide biosynthesis. Synthesis of CoA-thioesters is vital for the study of CoA-dependent enzymes and pathways, but also as standards for metabolomics studies. In this work we systematically tested five chemo-enzymatic methods for the synthesis of the three most abundant acyl-CoA thioester classes in biology; saturated acyl-CoAs, α,β-unsaturated acyl-CoAs (i.e., enoyl-CoA derivatives), and α-carboxylated acyl-CoAs (i.e., malonyl-CoA derivatives). Additionally we report on the substrate promiscuity of three newly described acyl-CoA dehydrogenases that allow the simple conversion of acyl-CoAs into enoyl-CoAs. With these five methods, we synthesized 26 different CoA-thioesters with a yield of 40% or higher. The CoA esters produced range from short- to long-chain, include branched and α,β-unsaturated representatives as well as other functional groups. Based on our results we provide a general guideline to the optimal synthesis method of a given CoA-thioester in respect to its functional group(s) and the commercial availability of the precursor molecule. The proposed synthetic routes can be performed in small scale and do not require special chemical equipment, making them convenient also for biological laboratories.
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