287955-93-5

Basic information

• Product Name: Butanoic acid, 4-cyano-3-hydroxy-, (3R)-
• Synonyms: Butanoic acid, 4-cyano-3-hydroxy-, (3R)-
• CAS NO: 287955-93-5
• Molecular Formula: C₅H₇NO₃
• Molecular Weight: 129.11398
• Mol File: 287955-93-5.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Butanoic acid, 4-cyano-3-hydroxy-, (3R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Butanoic acid, 4-cyano-3-hydroxy-, (3R)-(287955-93-5)
• EPA Substance Registry System: Butanoic acid, 4-cyano-3-hydroxy-, (3R)-(287955-93-5)

Safety Data

• Hazardous Substances Data: 287955-93-5(Hazardous Substances Data)

Upstream product

• 141942-85-0 (R)-ethyl 4-cyano-3-hydroxybutyrate 
• 13880-89-2 3-hydroxyglutaronitrile 

Downstream Products

• 669013-16-5 [3-((R)-4-Cyano-3-hydroxy-butyrylamino)-propyl]-carbamic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 
• 141942-85-0 (R)-ethyl 4-cyano-3-hydroxybutyrate 
• 312745-91-8 (S)-3-hydroxy-4-cyanobutyric acid ethyl ester 
• 287955-97-9 (R)-4-cyano-3-hydroxybutyric acid benzyl ester 
• 794520-41-5 C₃₂H₃₈N₂O₅ 
• 147028-56-6 (S)-(+)-methyl-(3-O--4-cyano)-butanoate 
• 669013-14-3 (3-{(R)-4-Cyano-3-[(2-cyano-ethoxy)-diisopropylamino-phosphanyloxy]-butyrylamino}-propyl)-carbamic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 

Relevant articles and documents

Creation of a productive, highly enantioselective nitrilase through gene site saturation mutagenesis (GSSM)

Gene site saturation mutagenesis (GSSM) technology is applied for the directed evolution of a nitrilase. The nitrilase effectively catalyzes the desymmetrization of the prochiral substrate 3-hydroxyglutaronitrile to afford (R)-4-cyano-3-hydroxybutyric acid, a precursor to the valuable cholesterol-lowering drug Lipitor. The discovered wild-type enzyme effectively performs the reaction at the industrially relevant 3 M substrate concentration but affords a product enantiomeric excess of only 87.6% ee. Through GSSM, a mutagenesis technique that effects the combinatorial saturation of each amino acid in the protein to each of the other 19 amino acids, combined with a novel high-throughput mass spectroscopy assay, a number of improved variants were identified, the best of which is the Ala190His mutant that yields product enantiomeric excess of 98.5% at 3 M substrate loading and a volumetric productivity of 619 g L-1 d-1. Copyright

Nitrilases, nucleic acids encoding them and methods for making and using them

The invention relates to nitrilases and to nucleic acids encoding the nitrilases. In addition methods of designing new nitrilases and method of use thereof are also provided. The nitrilases have increased activity and stability at increased pH and temperature.

Nitrilase-catalysed desymmetrisation of 3-hydroxyglutaronitrile: Preparation of a statin side-chain intermediate

An efficient, scaleable synthesis of ethyl (R)-4-cyano-3-hydroxybutyrate, a potential intermediate in the synthesis of Atorvastatin (Lipitor), has been developed. The three-stage process starts with reaction of low-cost epichlorohydrin with cyanide to give 3-hydroxyglutaronitrile (3-HGN). The second stage utilises a nitrilase-catalysed desymmetrisation of 3-HGN. The nitrilase reaction has been optimized to work at 3 M (330 g/L) substrate concentration, pH 7.5,27 °C. Under these conditions, with an enzyme loading of 6 wt %, 100% conversion and 99% ee product is obtained in 16 h. This material is then esterified to give the target compound, ethyl (R)-4-cyano-3-hydroxybutyrate. The cost-effectiveness of the process is determined by three factors: use of a low-cost starting material, the introduction of the chiral centre by desymmetrisation as opposed to kinetic resolution, and the use of Pfenex Expression Technology to allow a lower-cost supply of biocatalyst.