HPLC of Formula: 53562-86-0. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: (S)-Methyl 3-hydroxybutanoate, is researched, Molecular C5H10O3, CAS is 53562-86-0, about Inversion of cpADH5 Enantiopreference and Altered Chain Length Specificity for Methyl 3-Hydroxyalkanoates. Author is Ensari, Yunus; Dhoke, Gaurao V.; Davari, Mehdi D.; Bocola, Marco; Ruff, Anna Joelle; Schwaneberg, Ulrich.
Expanding the substrate scope of enzymes opens up new routes for synthesis of valuable chems. Ketone-functionalized fatty acid derivatives and corresponding chiral alcs. are valuable building blocks for the synthesis of a variety of chems. including pharmaceuticals. The alc. dehydrogenase from Candida parapsilosis (cpADH5) catalyzes the reversible oxidations of chiral alcs. and has a broad substrate range; a challenge for cpADH5 is to convert alcs. with small substituents (Me or ethyl) next to the oxidized alc. moiety. Mol. docking studies revealed that W286 is located in the small binding pocket and limits the access to substrates that contain aliphatic chains longer than Et substituent. In the current manuscript, we report that positions L119 and W286 are key residues to boost oxidation of medium chain Me 3-hydroxy fatty acids; interestingly the enantiopreference toward Me 3-hydroxybutyrate was inverted. Kinetic characterization of W286A showed a 5.5 fold increase of Vmax and a 9.6 fold decrease of Km values toward Me 3-hydroxyhexanoate (Vmax: 2.48 U mg- and Km: 4.76 mM). Simultaneous saturation at positions 119 and 286 library yielded a double mutant (L119M/W286S) with more than 30-fold improved activity toward Me 3-hydroxyoctanoate (WT: no conversion; L119M/W286S: 30 %) and inverted enantiopreference (S-enantiomer ≥99 % activity decrease and R-enantiomer >20-fold activity improvement) toward Me 3-hydroxybutyrate.
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