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Usage

Uses

Used in Microbiology:
(S)-3-Phenylbutyric Acid is used as a sole carbon and energy source in the isolation of Rhodococcus rhodochrous PB1 from compost soil. This application aids in the identification and study of specific microorganisms that can utilize (S)-3-PHENYLBUTYRIC ACID for growth, which can be valuable in understanding the metabolic capabilities of certain bacteria and their potential applications in biotechnology.
Used in Pharmaceutical Industry:
(S)-3-Phenylbutyric Acid is used in the design and synthesis of 2-Acylaminopyridin-4-ylimidazoles as p38 MAP kinase inhibitors. These inhibitors play a crucial role in the treatment of various inflammatory disorders by targeting the p38 MAP kinase pathway, which is involved in the regulation of cellular responses to stress and inflammation. By inhibiting this pathway, the resulting compounds can help alleviate symptoms and reduce the severity of inflammatory conditions.

Purification Methods

Purify the acids as the 2-isomer above, i.e. by distillation, but under a good vacuum. [Prelog & Scherrer Helv Chim Acta 42 2227 1959, Levene & Marker J Biol Chem 93 761 1932, 100 685 1933, Cram J Am Chem Soc 74 2137 1952.] The R-amide crystallises from H2O, with m 101.5-102o, and [] 20 -16.5o (c 1.2, EtOH). The racemic acid has m 39-40o, b 134-136o/6mm, 158o/12mm [Marvel et al. J Am Chem Soc 62 3499 1940]. [Beilstein 9 IV 1813.]

Upstream product

• 142-96-1 dibutyl ether 
• 54082-38-1 (-)-O-(3-Phenyl-cis-crotonoyl)-menthol 
• 4593-90-2 3-phenylbutyric acid 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 3756-41-0 (S)-(1-chloroethyl)benzene 
• 105-53-3 diethyl malonate 
• 57403-82-4 (4S)-4r-methoxymethyl-5t-phenyl-2-trans-propenyl-4,5-dihydro-oxazole 
• 591-51-5 phenyllithium 
• 107-93-7 (E)-but-2-enoic acid 
• 1533-20-6 1,3-diphenylbutane-1-one 
• 704-79-0 (Z)-3-phenylbut-2-enoic acid 
• 104282-53-3 (S)-3-Phenyl-butyric acid (1R,2S,3R,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 704-80-3 (E)-3-phenyl-2-butenoic acid 
• 64-17-5 ethanol 

Downstream Products

• 935-77-3 (S)-3-methyl-1-indanone 
• 2031-46-1 (3S)-3-phenylbutan-1-ol 
• 68679-84-5 (S)-3-phenyl butyric acid chloride 
• 1441-20-9 (R)-(-)-3-phenylbutyric acid methyl ester 
• 909785-77-9 (S)-chloromethyl 3-phenylbutanoate 
• 162127-97-1 (S)-2,2-Dimethyl-5-phenyl-hexan-3-one 
• 187811-73-0 ((Z)-(S)-1-tert-Butyl-3-phenyl-but-1-enyloxy)-trimethyl-silane 
• 108346-46-9 (2S,2'R,4S,4'S)-(+)-2,2'-dichloro-4,4'-diphenyl-2,2'-azopentane 
• 108346-47-0 (2S,2'R,4S,4'S)-(+)-2,2'-dimethyl-4,4'-diphenyl-2,2'-azopentanenitrile 
• 1026700-50-4 C₁₀H₁₃BrMg 
• 88564-05-0 (S)-2-((S)-3-Phenyl-butyl)-undecane-1,2-diol 
• 88564-06-1 (R)-2-((S)-3-Phenyl-butyl)-undecane-1,2-diol 

Relevant academic research and scientific papers

Asymmetric conjugate addition reactions with chiral oxadiazinones: Unusual conformational properties of the oxadiazinones

A series of Ephedra based oxadiazinones have been prepared, acylated, and examined in the asymmetric conjugate addition reaction with Grignard reagents in the presence of copper(I) bromide-dimethyl sulfide complex. The highest diastereoselectivity that was obtained in the conjugate addition reaction was observed with the (1R,2S)-ephedrine based N4-methyloxadiazinone (5:1 d.r.) favoring the formation of the (S)-configuration of the conjugate addition product. Efforts to enhance the level of diastereoselection via increasing the steric volume of the stereo-directing N4-substituent of the oxadiazinone (N4- = p-methoxyphenyl or -isopropyl) led to an observed decrease in the level of diastereoselection. A computational study was conducted to examine the conformations adopted by the N4-methyloxadiazinone vs. the N4-isopropyl-oxadiazinone that yielded the lower diastereoselectivity. An argument is made for the stereoelectronic properties of the N4-substituent being the cause of both the moderate diastereoselectivity and the unexpected facial preference for the conjugate addition.

CuH-Catalyzed Asymmetric Reductive Amidation of α,β-Unsaturated Carboxylic Acids

The direct enantioselective copper hydride (CuH)-catalyzed synthesis of β-chiral amides from α,β-unsaturated carboxylic acids and secondary amines under mild reaction conditions is reported. The method utilizes readily accessible carboxylic acids and tolerates a variety of functional groups in the β-position including several heteroarenes. A subsequent iridium-catalyzed reduction to γ-chiral amines can be performed in the same flask without purification of the intermediate amides.

Cobalt-Catalyzed Asymmetric Hydrogenation of α,β-Unsaturated Carboxylic Acids by Homolytic H2 Cleavage

The asymmetric hydrogenation of α,β-unsaturated carboxylic acids using readily prepared bis(phosphine) cobalt(0) 1,5-cyclooctadiene precatalysts is described. Di-, tri-, and tetra-substituted acrylic acid derivatives with various substitution patterns as well as dehydro-α-amino acid derivatives were hydrogenated with high yields and enantioselectivities, affording chiral carboxylic acids including Naproxen, (S)-Flurbiprofen, and a d-DOPA precursor. Turnover numbers of up to 200 were routinely obtained. Compatibility with common organic functional groups was observed with the reduced cobalt(0) precatalysts, and protic solvents such as methanol and isopropanol were identified as optimal. A series of bis(phosphine) cobalt(II) bis(pivalate) complexes, which bear structural similarity to state-of-the-art ruthenium(II) catalysts, were synthesized, characterized, and proved catalytically competent. X-band EPR experiments revealed bis(phosphine)cobalt(II) bis(carboxylate)s were generated in catalytic reactions and were identified as catalyst resting states. Isolation and characterization of a cobalt(II)-substrate complex from a stoichiometric reaction suggests that alkene insertion into the cobalt hydride occurred in the presence of free carboxylic acid, producing the same alkane enantiomer as that from the catalytic reaction. Deuterium labeling studies established homolytic H2 (or D2) activation by Co(0) and cis addition of H2 (or D2) across alkene double bonds, reminiscent of rhodium(I) catalysts but distinct from ruthenium(II) and nickel(II) carboxylates that operate by heterolytic H2 cleavage pathways.

Folding Assessment of Incorporation of Noncanonical Amino Acids Facilitates Expansion of Functional-Group Diversity for Enzyme Engineering

Protein design is limited by the diversity of functional groups provided by the canonical protein ?building blocks“. Incorporating noncanonical amino acids (ncAAs) into enzymes enables a dramatic expansion of their catalytic features. For this, quick identification of fully translated and correctly folded variants is decisive. Herein, we report the engineering of the enantioselectivity of an esterase utilizing several ncAAs. Key for the identification of active and soluble protein variants was the use of the split-GFP method, which is crucial as it allows simple determination of the expression levels of enzyme variants with ncAA incorporations by fluorescence. Several identified variants led to improved enantioselectivity or even inverted enantiopreference in the kinetic resolution of ethyl 3-phenylbutyrate.

OPIOID RECEPTOR MODULATORS AND PRODUCTS AND METHODS RELATED THERETO

Compounds are provided having the structure of Formula (I): or a pharmaceutically acceptable isomer, racemate, hydrate, solvate, isotope, or salt thereof, wherein A, B, L, R3, R4, R5, R6, R8, m and n are as defined herein. Such compounds modulate the opioid receptor, particulare the mu-opioid receptor (MOR) and/or the kappa-opioid receptor (KOR), and/or the delta-opioid receptor (DOR). Products containing such compounds, as well as methods for their use and preparation, are also provided.

Identification of an Esterase Isolated Using Metagenomic Technology which Displays an Unusual Substrate Scope and its Characterisation as an Enantioselective Biocatalyst

Evaluation of an esterase annotated as 26D isolated from a marine metagenomic library is described. Esterase 26D was found to have a unique substrate scope, including synthetic transformations which could not be readily effected in a synthetically useful manner using commercially available enzymes. Esterase 26D was more selective towards substrates which had larger, more sterically demanding substituents (i. e. iso-propyl or tert-butyl groups) on the β-carbon, which is in contrast to previously tested commercially available enzymes which displayed a preference for substrates with sterically less demanding substituents (e.g. methyl group) at the β-carbon. (Figure presented.).

Enantioselective Hydrogenation of β,β-Disubstituted Unsaturated Carboxylic Acids under Base-Free Conditions

An additive-free enantioselective hydrogenation of β,β-disubstituted unsaturated carboxylic acids catalyzed by the Rh-(R,R)-f-spiroPhos complex has been developed. Under mild conditions, a wide scope of β,β-disubstituted unsaturated carboxylic acids were hydrogenated to the corresponding chiral carboxylic acids with excellent enantioselectivities (up to 99.3% ee). This methodology was also successfully applied to the synthesis of the pharmaceutical molecule indatraline.

Rhodium(I)-catalyzed enantioselective hydrogenation of substituted acrylic acids with sterically similar β,β-diaryls

Distinct differentiation: β,β-Disubstituted acrylic acids with sterically similar geminal diaryl groups can be hydrogenated with excellent enantioselectivities in the presence of a RhI complex formed in situ with two-component ligands, a chiral secondary phosphine oxide (SPO) and an achiral phosphine (Ph3P). The sense of asymmetric induction was found to be controlled by the substrate configuration, thus allowing access to both enantiomers of the product with the same catalyst. Copyright

Influence of the position of the substituent on the efficiency of lipase-mediated resolutions of 3-aryl alkanoic acids

Hydrolase-catalysed kinetic resolutions to provide enantioenriched α-substituted 3-aryl alkanoic acids are described. (S)-2-Methyl-3- phenylpropanoic acid (S)-1a was prepared in 96% ee by Pseudomonas fluorescens catalysed ester hydrolysis, while, Candida antarctica lipase B (immob) resolved the α-ethyl substituted 3-arylalkanoic acid (R)-1b in 82% ee. The influence of the position of the substituent relative to the ester site on the efficiency and enantioselectivity of the biotransformation is also explored; the same lipases were found to resolve both the α- and β-substituted alkanoic acids. Furthermore, the steric effect of substituents at the C2 stereogenic centre relative to that for their C3 substituted counterparts on the efficiency and stereoselectivity is discussed.

Enantioselective oxidation of aldehydes catalyzed by alcohol dehydrogenase

Teaching old dogs new tricks: Alcohol dehydrogenases (ADHs) may be established redox biocatalysts but they still are good for a few surprises. ADHs can be used to oxidize aldehydes, and this was demonstrated by the oxidative dynamic kinetic resolution of profens. In the presence of a suitable cofactor regeneration system, this reaction can occur with high selectivity. Copyright