Galactose oxidase and alcohol oxidase: Scope and limitations for the enzymatic synthesis of aldehydes

Oxidation with galactose oxidase: Multifunctional enzymatic catalysis

“…Most simply, the reactions were conducted in an open flask with stirring [26,40]. In an effort to further increase oxygen concentration in reaction mixtures, an O 2 balloon has been attached to the reaction flask [3], and O 2 gas has been flushed into reaction media either continuously [33] or in short periods [31,47]. However, the impact of these various techniques on product yield did not significantly differ (Table 1 and 2).…”

“…Siebum et al studied 18 potential substrates, of which most were small alcohols ( Figure 3) [3]. Conversions of most of these molecules, determined by 1 H NMR, were very low; 1 and 5% for glycerol and 1,2-dihydroxybutane, respectively, and undetectable for most other substrates, even though initial reaction rates could be determined by a hydrogen peroxide coupled assay.…”

“…The exact structures of the other oxidation products were not described. The requirement of having a fragment similar to the C-4 -C-6 conformation of galactose is further discussed [3]. Notably, GAO-catalyzed oxidation of glycerol, yielding 6%, was utilized as the intermediate step in the synthesis of Lfructose.…”

“…In addition to constructing a glucose 6-oxidase from GAO, enzyme engineering efforts have created GAO variant (M [3][4][5] ) that catalyse the enantioselective oxidization of secondary alcohols [98] and GAO variants (H 1 and F 2 ) that selectively oxidize glycans on glycoproteins [99]. While variant M [3][4][5] has been used to synthesize optically pure secondary alcohols and atropisomeric diaryl ethers [98,100], improved activity of H 1 and F 2 on D-mannose and D-N-acetyl glucosamine enabled selective labelling of glycoproteins in solution or present on the surface of whole cells [99].…”

A Synergic Blend of Newly Isolated Pseudomonas mandelii KJLPB5 and [hmim]Br for Chemoselective 2° Aryl Alcohol Oxidation in H2O2: Synthesis of Aryl Ketone or Aldehydes via Sequential Dehydration-Oxidative C=C Cleavage

“…A number of biocatalytic reports are available for the synthesis of carbonyls either by oxidation of alcohols [21][22][23][24] or by oxidative alkene cleavage [25][26][27]. Still, the development of chemoselective methods that efficiently discriminate among various functional groups remains challenging.…”