28549-12-4

Usage

Uses

Used in Pharmaceutical Industry:
(S)-Hydroxyphenylacetonitrile is used as a key intermediate in the production of various pharmaceuticals, including anti-cancer drugs and antibiotics. Its unique structure and reactivity make it a valuable component in the synthesis of these life-saving medications.
Used in Organic Chemistry:
(S)-Hydroxyphenylacetonitrile is used as a building block in organic chemistry for the synthesis of chiral compounds. Its ability to form various derivatives and participate in different chemical reactions makes it a versatile component in the creation of complex organic molecules.
Used in Chemical Research:
Due to its unique properties and potential applications, (S)-Hydroxyphenylacetonitrile is a subject of interest in chemical research. Scientists are exploring its reactivity, potential applications, and methods for its synthesis and modification to enhance its utility in various fields.

Upstream product

• 108-05-4 vinyl acetate 
• 532-28-5 (RS)-mandelonitrile 
• 61066-82-8 2-(Butyryloxy)-2-phenylethannitril 
• 129265-89-0 2-(Hexanoyloxy)-2-phenylethannitril 
• 86013-39-0 (R)-((R)-1-Methyl-3-oxo-butoxy)-phenyl-acetonitrile 
• 74-90-8 hydrogen cyanide 
• 100-52-7 benzaldehyde 
• 7677-24-9 trimethylsilyl cyanide 
• 13435-20-6 tetraethylammoniumcyanide 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 147329-41-7 (S)-α-(4-nitrobenzoyloxy)benzeneacetonitrile 
• 147329-44-0 (S)-α-diphenylacetoxy-benzeneacetonitrile 
• 151-50-8 potassium cyanide 
• 25438-37-3 phenyl(trimethylsiloxy)acetonitrile 

Downstream Products

• 131350-12-4 (S)-2-phenyl-2-(trimethylsiloxy)acetonitrile 
• 147329-37-1 (S)-(-)-α-<(tert-butyldimethylsilyl)oxy>benzeneacetonitrile 
• 67755-90-2 (S)-2-(1-ethoxyethoxy)-2-phenylacetonitrile 
• 119718-88-6 O-acetyl (S)-mandelonitrile 
• 66867-29-6 (2S)-O-methoxycarbonyl-2-hydroxy-2-phenyl-acetonitrile 
• 182823-61-6 (R)-1-[(S)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-propylamine 
• 182823-60-5 (S)-1-[(S)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-propylamine 
• 182823-59-2 (R)-1-[(S)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-pentylamine 
• 182823-58-1 (S)-1-[(S)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-pentylamine 
• 129687-09-8 (R)-1-[(S)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-2-methyl-butylamine 
• 129687-09-8 (S)-1-[(S)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-2-methyl-butylamine 
• 182823-63-8 (R)-1-[(S)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-hexylamine 
• 182823-62-7 (S)-1-[(S)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-hexylamine 
• 182823-65-0 (R)-1-[(S)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-heptylamine 

Relevant academic research and scientific papers

Expression of hydroxynitrile lyase from Manihot esculenta in yeast and its application in (S)-mandelonitrile production using an immobilized enzyme reactor

Hydroxynitrile lyase from cassava, Manihot esculenta (MeHNL), catalyzes the formation of (S)-cyanohydrins from HCN and aldehydes or ketones. (S)-Mandelonitrile was produced on a bench scale with immobilized MeHNL, after optimizing the enzyme expression sy

Immobilized hydroxynitrile lyase: A comparative study of recyclability

Hydroxynitrile lyase from cassava, Manihot esculenta, (MeHNL) catalyzes the formation of (S)-cyanohydrins from HCN and aldehydes or ketones. Four differently immobilized MeHNLs were prepared: by noncovalent immobilization (celite R-633), covalent immobili

Light controlled reversible inversion of nanophosphor-stabilized pickering emulsions for biphasic enantioselective biocatalysis

In this work, by utilizing photochromic spiropyrans conjugated upconversion nanophosphors, we have successfully prepared NIR/visible light tuned interfacially active nanoparticles for the formulation of Pickering emulsions with reversible inversion properties. By loading a model enantioselective biocatalytic active bacteria Alcaligenes faecalis ATCC 8750 in the aqueous phase, we demonstrated for the first time that the multifunctional Pickering emulsion not only highly enhanced its catalytic performance but also relieved the substrate inhibition effect. In addition, product recovery, and biocatalysts and colloid emulsifiers recycling could be easily realized based on the inversion ability of the Pickering emulsion. Most importantly, the utilization of NIR/visible light to perform the reversible inversion without any chemical auxiliaries or temperature variation showed little damage toward the biocatalysts, which was highlighted by the high catalytic efficiency and high enantioselectivity even after 10 cycles. The NIR/visible light controlled Pickering emulsion showed promising potential as a powerful technique for biocatalysis in biphasic systems.

Probing batch and continuous flow reactions in organic solvents:Granulicella tundricolahydroxynitrile lyase (GtHNL)

Granulicella tundricolahydroxynitrile lyase (GtHNL) is a manganese dependent cupin which catalyses the enantioselective synthesis of (R)-cyanohydrins. TheGtHNL triple variant A40H/V42T/Q110H, previously reported to exhibit a high activity and stability, w

A study on increasing enzymatic stability and activity of Baliospermum montanum hydroxynitrile lyase in biocatalysis

HNL catalysis is usually carried out in a biphasic solvent and at low pH to suppress the non-enzymatic synthesis of racemic cyanohydrins. However, enzyme stability under these conditions remain a challenge. We have investigated the effect of different biocatalytic parameters, i.e., pH, temperature, buffer concentrations, presence of stabilizers, organic solvents, and chemical additives on the stability of Baliospermum montanum hydroxynitrile lyase (BmHNL). Unexpectedly, glycerol (50 mg/mL) added BmHNL biocatalysis had produced >99% of (S)-mandelonitrile from benzaldehyde, while without glycerol it is 54% ee. Similarly, BmHNL had converted 3-phenoxy benzaldehyde and 3,5-dimethoxy benzaldehyde, to their corresponding cyanohydrins in the presence of glycerol. Among the different stabilizers added to BmHNL at low pH, 400 mg/mL of sucrose had increased enzyme's half-life more than fivefold. BmHNL's stability study showed half-lives of 554, 686, and 690 h at its optimum pH 5.5, temperature 20 °C, buffer concentration, i.e., 100 mM citrate-phosphate pH 5.5. Addition of benzaldehyde as inhibitor, chemical additives, and the presence of organic solvents have decreased both the stability and activity of BmHNL, compared to their absence. Secondary structural study by CD-spectrophotometer showed that BmHNL's structure is least affected in the presence of different organic solvents and temperatures.

Stabilization of Hydroxynitrile Lyases from Two Variants of Passion Fruit, Passiflora edulis Sims and Passiflora edulis Forma flavicarpa, by C-Terminal Truncation

Because the synthesis of chiral compounds generally requires a broad range of substrate specificity and stable enzymes, screening for better enzymes and/or improvement of enzyme properties through molecular approaches is necessary for sustainable industri

Hydroxynitrile lyases covalently immobilized in continuous flow microreactors

Enzymes are supreme catalysts when it comes to high enantiopurities and their immobilization will pave the way for continuous operation. In this context, we show the covalent immobilization of hydroxynitrile lyases HbHNL (from Hevea brasiliensis) and MeHN

Combining Photo-Organo Redox- and Enzyme Catalysis Facilitates Asymmetric C-H Bond Functionalization

In this study, we combined photo-organo redox catalysis and biocatalysis to achieve asymmetric C–H bond functionalization of simple alkane starting materials. The photo-organo catalyst anthraquinone sulfate (SAS) was employed to oxyfunctionalise alkanes to aldehydes and ketones. We coupled this light-driven reaction with asymmetric enzymatic functionalisations to yield chiral hydroxynitriles, amines, acyloins and α-chiral ketones with up to 99 % ee. In addition, we demonstrate functional group interconversion to alcohols, esters and carboxylic acids. The transformations can be performed as concurrent tandem reactions. We identified the degradation of substrates and inhibition of the biocatalysts as limiting factors affecting compatibility, due to reactive oxygen species generated in the photocatalytic step. These incompatibilities were addressed by reaction engineering, such as applying a two-phase system or temporal and spatial separation of the catalysts. Using a selection of eleven starting alkanes, one photo-organo catalyst and 8 diverse biocatalysts, we synthesized 26 products and report for the model compounds benzoin and mandelonitrile > 97 % ee at gram scale.

Supported Ionic Liquid-Like Phases (SILLPs) as Immobilised Catalysts for the Multistep and Multicatalytic Continuous Flow Synthesis of Chiral Cyanohydrins

Supported Ionic Liquid-Like Phases have been found to be efficient organocatalysts for the synthesis of cyanohydrin esters under solvent-free conditions by an “electrophile-nucleophile dual activation” based on hydrogen bond formation. The combination of

Immobilized Baliospermum montanum hydroxynitrile lyase catalyzed synthesis of chiral cyanohydrins

Hydroxynitrile lyase (HNL) catalyzed enantioselective C–C bond formation is an efficient approach to synthesize chiral cyanohydrins which are important building blocks in the synthesis of a number of fine chemicals, agrochemicals and pharmaceuticals. Immobilization of HNL is known to provide robustness, reusability and in some cases also enhances activity and selectivity. We optimized the preparation of immobilization of Baliospermium montanum HNL (BmHNL) by cross linking enzyme aggregate (CLEA) method and characterized it by SEM. Optimization of biocatalytic parameters was performed to obtain highest % conversion and ee of (S)-mandelonitrile from benzaldehyde using CLEA-BmHNL. The optimized reaction parameters were: 20 min of reaction time, 7 U of CLEA-BmHNL, 1.2 mM substrate, and 300 mM citrate buffer pH 4.2, that synthesized (S)-mandelonitrile in ～99% ee and ～60% conversion. Addition of organic solvent in CLEA-BmHNL biocatalysis did not improve in % ee or conversion of product unlike other CLEA-HNLs. CLEA-BmHNL could be successfully reused for eight consecutive cycles without loss of conversion or product formation and five cycles with a little loss in enantioselectivity. Eleven different chiral cyanohydrins were synthesized under optimal biocatalytic conditions in up to 99% ee and 59% conversion, however the % conversion and ee varied for different products. CLEA-BmHNL has improved the enantioselectivity of (S)-mandelonitrile synthesis compared to the use of purified BmHNL. Nine aldehydes not tested earlier with BmHNL were converted into their corresponding (S)-cyanohydrins for the first time using CLEA-BmHNL. Among the eleven (S)-cyanohydrins syntheses reported here, eight of them have not been synthesized by any CLEA-HNL. Overall, this study showed preparation, characterization of a stable, robust and recyclable biocatalyst i.e. CLEA-BmHNL and its biocatalytic application in the synthesis of different (S)-aromatic cyanohydrins.