Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via
3.3.3.3.9 Glycerol 3-Phosphate Oxidase

DOI: 10.1055/sos-SD-216-00052

Ewing, T. A.; Fraaije, M. W.; van Berkel, W. J. H.Science of Synthesis: Biocatalysis in Organic Synthesis, (20153171.

Glycerol 3-phosphate oxidase (GPO, EC 1.1.3.21) is a flavin adenine dinucleotide (FAD) dependent oxidase that catalyzes the oxidation of l-glycerol 3-phosphate to 1,3-dihydroxyacetone phosphate, which is a useful precursor for the synthesis of sugars by asymmetric aldol additions. Glycerol 3-phosphate oxidases from various bacterial sources are commercially available. Krämer and Steckhan have utilized immobilized glycerol 3-phosphate oxidase in combination with d-fructose 1,6-bisphosphate aldolase to convert l-glycerol 3-phosphate and glyceraldehyde into d-fructose 1-phosphate and l-sorbose 1-phosphate, which are subsequently dephosphorylated using acid phosphatase to obtain the unmodified monosaccharides.[‌91‌] Glycerol 3-phosphate oxidase has also been utilized in a one-pot multienzyme cascade reaction for the synthesis of the carbohydrate fragments 25 [R1 = Et, iPr, (CH2)2NHCO2CH2CH=CH2] starting from glycerol (23) and aldehydes 24 (Scheme 16).[‌92‌] In this cascade, glycerol (23) is first phosphorylated by an acid phosphatase, followed by the oxidation of the formed glycerol 3-phosphate to 1,3-dihydroxyacetone phosphate by glycerol 3-phosphate oxidase. Subsequently, the dihydroxyacetone phosphate is stereoselectively coupled to the relevant aldehyde by an aldolase, followed by dephosphorylation of the product by an acid phosphatase. The use of four aldolases with varying stereospecificities enables the synthesis of all four stereoisomers of 25, though in some cases the stereoselectivity of the coupling reaction is poor. When followed by reductive amination (H2, Pd/C), this enzymatic cascade can be utilized for the chemoenzymatic synthesis of the sugar d-fagomine 26 from glycerol and aldehyde 24 [R1 = (CH2)2NHCO2CH2CH=CH2].

Meeeee 88 Meeeeeeee ee Meeeeeeeeeee Meeeeeeee eeee Meeeeeee eee Meeeeeeee ee e Meeeeeeeeee Meeeeee Meeeeeeee Meeeeeee 8-Meeeeeeee Meeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeee 8,8,8-Meeeeeeeeeeeeee-8-eee Meeeeeeeeeee Meeeeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

Meeeee eeeee eeeeeeee (88 M · eM−8), eeeeeeeeeeeeeeee eeeeeeeee eeeeeeeee eeeeee eeeeee eeeeeeee (8 M · eM−8), eee eeeeeeee 8-eeeeeeeee eeeeeee (MMM; 88 M · eM−8) eeee eeeee ee e eeee eeeeeeeeee 888 eM eeeeeeee (88), 888 eM eeeeeeeeeeeee (Me8M8M8M8/Me8M8M8 8:8), eee 888 eM eeeeeeee 88 ee 88 eM MeMMe eeeeee (eM 8). Mee eeeeeeee eee eeeeeee ee eeeeee Meeeeeee eeeeeeee eeee eeeeeeeeeee (8 M · eM−8) eee eeeeeeeee ee 88 °M eeeee eeee eeeeeee eeeee eeeeeeeeee (ee eeeeeeeeee ee MMMM). Meeeeeeeeeeeeeeee ee eee eee eeeeeee eee eeeeeeeee eeeee 88 e eee eeeeee eee (8 e) eee eeeee. Mee eeeeeeee eeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeee eee eee eeeeee ee eee ee e eeeeee (eeeeee eee, MeMMe/MeMM 88:8). Mee eeee eeeeeeeee eeee eeeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee eee eeeeeee ee e eeeeee eee.

References


Cookie-Einstellungen