Sugar analog synthesis by in vitro biocatalytic cascade: A comparison of alternative enzyme complements for dihydroxyacetone phosphate production as a precursor to rare chiral sugar synthesis
| Autor: | Judith A. Scoble, Carol J. Hartley, Gregory W. Simpson, Colin Scott, Matthew C. Taylor, Quentin I. Churches, Andrew R. Frazer, Nicholas J. Turner, Greg Coia, Charlotte C. Williams, Nigel G. French |
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| Jazyk: | angličtina |
| Rok vydání: | 2017 |
| Předmět: |
0301 basic medicine
Glycerol Glycerol kinase Applied Microbiology lcsh:Medicine 01 natural sciences Biochemistry chemistry.chemical_compound Aldol reaction Glycerol Kinase lcsh:Science Enzyme Chemistry Chromatography High Pressure Liquid Acetate kinase Multidisciplinary biology Organic Compounds Stereoisomerism Catalase Enzymes Physical sciences Chemistry Dihydroxyacetone Phosphate Oxidoreductases Research Article Biotechnology Dihydroxyacetone Glycerolphosphate Dehydrogenase Monomers (Chemistry) Microbiology Catalysis Phosphates 03 medical and health sciences Industrial Microbiology DHAP Manchester Institute of Biotechnology Polymer chemistry Dehydrogenases Dihydroxyacetone phosphate Aldehydes 010405 organic chemistry Acetate Kinase lcsh:R Aldolase A Organic Chemistry Chemical Compounds Biology and Life Sciences Proteins ResearchInstitutes_Networks_Beacons/manchester_institute_of_biotechnology Combinatorial chemistry 0104 chemical sciences 030104 developmental biology chemistry Biocatalysis biology.protein Enzymology Cofactors (Biochemistry) lcsh:Q Sugars Catalases |
| Zdroj: | PLoS ONE Hartley, C J, French, N G, Scoble, J A, Williams, C C, Churches, Q I, Frazer, A R, Taylor, M C, Coia, G, Simpson, G, Turner, N J & Scott, C 2017, ' Sugar analog synthesis by in vitro biocatalytic cascade : A comparison of alternative enzyme complements for dihydroxyacetone phosphate production as a precursor to rare chiral sugar synthesis ', PLoS ONE, vol. 12, no. 11, e0184183 . https://doi.org/10.1371/journal.pone.0184183 PLoS ONE, Vol 12, Iss 11, p e0184183 (2017) |
| ISSN: | 1932-6203 |
| DOI: | 10.1371/journal.pone.0184183 |
| Popis: | Carbon-carbon bond formation is one of the most challenging reactions in synthetic organic chemistry, and aldol reactions catalysed by dihydroxyacetone phosphate-dependent aldolases provide a powerful biocatalytic tool for combining C-C bond formation with the generation of two new stereo-centres, with access to all four possible stereoisomers of a compound. Dihydroxyacetone phosphate (DHAP) is unstable so the provision of DHAP for DHAP-dependent aldolases in biocatalytic processes remains complicated. Our research has investigated the efficiency of several different enzymatic cascades for the conversion of glycerol to DHAP, including characterising new candidate enzymes for some of the reaction steps. The most efficient cascade for DHAP production, comprising a one-pot four-enzyme reaction with glycerol kinase, acetate kinase, glycerophosphate oxidase and catalase, was coupled with a DHAP-dependent fructose-1,6-biphosphate aldolase enzyme to demonstrate the production of several rare chiral sugars. The limitation of batch biocatalysis for these reactions and the potential for improvement using kinetic modelling and flow biocatalysis systems is discussed. |
| Databáze: | OpenAIRE |
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