50353-41-8Relevant academic research and scientific papers
Stereoselective oxidation of aryl-substituted vicinal diols into chiral α-hydroxy aldehydes by re-engineered propanediol oxidoreductase
Blikstad, Cecilia,Dahlstroem, Kaethe M.,Salminen, Tiina A.,Widersten, Mikael
, p. 3016 - 3025 (2014/01/06)
α-Hydroxy aldehydes are chiral building blocks used in synthesis of natural products and synthetic drugs. One route to their production is by regioselective oxidation of vicinal diols and, in this work, we aimed to perform the oxidation of 3-phenyl-1,2-propanediol into the corresponding α-hydroxy aldehyde applying enzyme catalysis. Propanediol oxidoreductase from Escherichia coli efficiently catalyzes the stereoselective oxidation of S-1,2-propanediol into S-lactaldehyde. The enzyme, however, shows no detectable activity with aryl-substituted or other bulky alcohols. We conducted ISM-driven directed evolution on FucO and were able to isolate several mutants that were active with S-3-phenyl-1,2-propanediol. The most efficient variant displayed a kcat/KM of 40 s-1 M-1 and the most enantioselective variant an E-value (S/R) of 80. Furthermore, other isolated variants showed up to 4400-fold increased activity with another bulky substrate, phenylacetaldehyde. The results with engineered propanediol oxidoreductases identified amino acids important for substrate selectivity and asymmetric synthesis of aryl-substituted α-hydroxy aldehydes. In conclusion, our study demonstrates the feasibility of tailoring the catalytic properties of propanediol oxidoreductase for biocatalytic properties.
Influence of α-methyl substitution of proline-based organocatalysts on the asymmetric α-oxidation of aldehydes
Tong, Sok-Teng (Amy),Brimble, Margaret A.,Barker, David
experimental part, p. 4801 - 4807 (2009/10/09)
The direct asymmetric organocatalytic α-oxidation of aldehydes using trans-2-(p-methylphenylsulfonyl)-3-phenyloxaziridine is reported. This method affords the S isomer of α-hydroxy aldehydes, thereby complementing the selectivity for the R isomer observed using the two-step nitrosobenzene method. Use of α-methylproline and α-methylproline tetrazole significantly increases the enantioselectivity observed for the α-oxidation of aldehydes compared to analogous unsubstituted organocatalysts.
Synthesis of Enantiomerically Pure α-Hydroxyaldehydes from the Corresponding α-Hydroxycarboxylic acids: Novel Substrates for Escherichia coli Transketolase
Humphrey, Andrew J.,Turner, Nicholas J.,McCague, Raymond,Taylor, Stephen J. C.
, p. 2475 - 2476 (2007/10/03)
Enantiomerically pure (R)-α-hydroxyaldehydes (>95percent ee) are prepared from the corresponding α-hydroxyesters by silyl protection, reduction with diisobutylaluminium hydride, and finally deprotection under acidic conditions; subsequent coupling of these aldehydes with lithium hydroxypyruvate, catalysed by Escherichia coli transketolase, leads to novel optically pure triols.
