123802-80-2Relevant articles and documents
Chemoenzymatic Production of Enantiocomplementary 2-Substituted 3-Hydroxycarboxylic Acids from l-α-Amino Acids
Pickl, Mathias,Marín-Valls, Roser,Joglar, Jesús,Bujons, Jordi,Clapés, Pere
, p. 2866 - 2876 (2021/04/14)
A two-enzyme cascade reaction plus in situ oxidative decarboxylation for the transformation of readily available canonical and non-canonical l-α-amino acids into 2-substituted 3-hydroxycarboxylic acid derivatives is described. The biocatalytic cascade consisted of an oxidative deamination of l-α-amino acids by an l-α-amino acid deaminase from Cosenzaea myxofaciens, rendering 2-oxoacid intermediates, with an ensuing aldol addition reaction to formaldehyde, catalyzed by metal-dependent (R)- or (S)-selective carboligases namely 2-oxo-3-deoxy-l-rhamnonate aldolase (YfaU) and ketopantoate hydroxymethyltransferase (KPHMT), respectively, furnishing 3-substituted 4-hydroxy-2-oxoacids. The overall substrate conversion was optimized by balancing biocatalyst loading and amino acid and formaldehyde concentrations, yielding 36–98% aldol adduct formation and 91–98% ee for each enantiomer. Subsequent in situ follow-up chemistry via hydrogen peroxide-driven oxidative decarboxylation afforded the corresponding 2-substituted 3-hydroxycarboxylic acid derivatives. (Figure presented.).
Synthesis of Enantiomerically Enriched 2-Hydroxymethylalkanoic Acids by Oxidative Desymmetrisation of Achiral 1,3-Diols Mediated by Acetobacter aceti
Brenna, Elisabetta,Cannavale, Flavia,Crotti, Michele,De Vitis, Valerio,Gatti, Francesco G.,Migliazza, Gaia,Molinari, Francesco,Parmeggiani, Fabio,Romano, Diego,Santangelo, Sara
, p. 3796 - 3803 (2016/12/24)
The stereoselective desymmetrisation of achiral 2-alkyl-1,3-diols is performed by oxidation of one of the two enantiotopic primary alcohol moieties by means of Acetobacter aceti MIM 2000/28 to afford the corresponding chiral 2-hydroxymethyl alkanoic acids (up to 94 % ee). The procedure, carried out in aqueous medium under mild conditions of pH, temperature and pressure, contributes to enlarge the portfolio of enzymatic oxidations available to organic chemists for the development of sustainable manufacturing processes.
Synthesis of chiral α-benzyl-β2-hydroxy carboxylic acids through iridium-catalyzed asymmetric hydrogenation of α- oxymethylcinnamic acids
Li, Ze-Yu,Song, Song,Zhu, Shou-Fei,Guo, Na,Wang, Li-Xin,Zhou, Qi-Lin
, p. 783 - 787 (2014/10/16)
An asymmetric hydrogenation of α-oxymethylcinnamic acids was developed by using chiral spiro phosphine-oxazoline/iridium complexes as catalysts to prepare β2-hydroxycarboxylic acids with high reactivity (TON up to 2000) and excellent enantioselectivity (up to 99.5% ee). By using this highly efficient asymmetric hydrogenation as a key step, a concise total synthesis of natural product homoisoflavone (S)-(+)-4 was accomplished. An asymmetric hydrogenation of α-oxymethylcinnamic acids was developed to prepare β2-hydroxycarboxylic acids with high reactivity (TON up to 2000) and excellent enantioselectivity (up to 99.5% ee), which was applied to a concise total synthesis of a natural product homoisoflavone. Copyright
