Regiospecific Enzymatic Hydroxylations of Pyrazinecarboxylic Acid and a Practical Synthesis of 5-Chloropyrazine-2-Carboxylic Acid

A Single Enzyme Oxidative “Cascade” via a Dual-Functional Galactose Oxidase

“…2 The spectrum of accessible products could be easily diversified to include variously substituted ring structures as well, some of which are versatile intermediates in pharmaceuticals or drug library production and can be made either biocatalytically by other oxidizing enzymes or even chemically after formation of the acid. [22][23][24] Additionally, the finding that GOase had little to no activity toward ortho-substituted benzaldehydes and differences in activity based on substitution patterns creates a potential means for selectively oxidizing dialdehyde substrates. Targeted, single oxidation of substituted tere-or isophthalaldehyde derivatives by GOase would produce aromatic mono-acid/mono-aldehyde building blocks with a third unique chemical handle on the ring.…”

Biocatalysis making waves in organic chemistry

“…192,193 Next to the above-mentioned oxygenases, also a range of dehydrogenases are known (and used industrially) for the orthohydroxylation of pyridines (Scheme 20). [194][195][196] The O-atom introduced does not stem from molecular oxygen (as to be expected from a monooxygenase-catalysed hydroxylation) but from water. 197 The mechanism of this reaction is yet to be elucidated.…”

Lonza: Biotechnology – A Key Ingredient for Success in the Future

“…Methyl group oxidation heteroaromatic compounds [3] Ethyl group oxidation heteroaromatic compounds [4] Selective oxidation polyols [5,6] Hydroxylation heteroaromatic carboxylic acids [7,8,9,10] stereoselective hydroxylation of unactivated carbons [11,12] Reduction Carbonyl reduction β-oxo esters [13,14] Double bond reduction activated enols [15,16] alkenes b Hydrolysis Acetyl hydrolysis α-aminoacids Penicillin [17,18] Ester hydrolysis α-hydroxy carboxylic acids esters [19] Nitrile partial hydrolysis N-containing heterocyclic cyanides [20][21][22][23]24] Amide hydrolysis N-containing heterocylic 2-carboxamides [21,25,26,27] Amination Transamination N-containing-3-amino heterocycles (asymmetric synthesis) [28] N-containing-3-oxo heterocycles (racemic resolution) [ metagenomics, modeling and quantitative structure-activity relationship (3D-QSAR) [31] and increasing advances in instrumentation which allows extremely high throughput screening protocols to be executed. -the increasing public and government awareness of global warming and the necessity to implement environmentally friendly processes.…”