20016-85-7Relevant academic research and scientific papers
Enzymatic Resolution of Chiral 2-Hydroxy Carboxylic Acids by Enantioselective Oxidation with Molecular Oxygen Catalyzed by the Glycolate Oxidase from Spinach (Spinacia oleracea)
Adam, Waldemar,Lazarus, Michael,Boss, Barbara,Saha-Moeller, Chantu R.,Humpf, Hans-Ulrich,Schreier, Peter
, p. 7841 - 7843 (2007/10/03)
The enzymatic oxidation of a variety of saturated and unsaturated aliphatic derivatives of racemic 2-hydroxy acids 1 to their 2-oxo acids 2 with molecular oxygen catalyzed by the glycolate oxidase from spinach (Spinacia oleracea) was shown to proceed highly enantioselectively.Thus, the glycolate oxidase-catalyzed kinetic resolution provides a convenient biocatalytic method for the preparation of enantiomerically pure (R)-2-hydroxy acids.The absolute configuration of the (R)-2-hydroxy acid 1b assigned by comparison of the measured optical rotation value with that of the literature data and by application of the exciton-coupled circular dichroism method (ECCD) on its bichromophoric 2-naphthoate 9-methylanthryl derivative 3b.These results establish the ECCD method as a convenient microscale chirooptic tool for the configurational assignment of 2-hydroxy acids.
A Novel Bicyclic Orthoester as a Chiral Auxiliary: Application to the Synthesis of α-Hydroxy Acids
Dube, D.,Deschenes, D.,Tweddell, J.,Gagnon, H.,Carlini, R.
, p. 1827 - 1830 (2007/10/02)
Chiral α-keto orthoesters derived from tartanic acid can be reduced diastereoselectively.Hydrolysis affords optically actice α-hydroxy acids and the recovered auxiliary.
A SYNTHON FOR CHIRAL GLYCOLATE ENOLATE (ROC-HCOOR'): A CAMPHOR-BASED OXAZOLINE
Kelly, T. Ross,Arvanitis, Argyrios
, p. 39 - 42 (2007/10/02)
Alkylations of the anion (7a) derived from a camphor-based oxazoline proceed in good yield.Hydrolysis affords the corresponding α-hydroxy acids in high ee.
