52358-06-2

Upstream product

• 4111-12-0 (+/-)-2-methyl-2-hydroxyhexanenitrile 
• 66-25-1 hexanal 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 74-90-8 hydrogen cyanide 
• 40326-17-8 2-Trimethylsilanyloxy-heptanenitrile 
• 7677-24-9 trimethylsilyl cyanide 
• 4746-48-9 2-hydroxy-2,2-diphenylacetonitrile 

Downstream Products

• 66478-41-9 (Z)-2-heptenenitrile 
• 52358-06-2 (R)-2-hydroxyheptanenitrile 
• 78749-39-0 5-Cyanohexanoic acid 
• 95577-45-0 4-cyanohexanoic acid 
• 142-62-1 hexanoic acid 
• 93292-63-8 (S)-2-(tert-butyldiphenylsilyloxy)heptanal 
• 1610457-89-0 C₂₃H₃₁NOSi 
• 1585968-98-4 [(5R,6R)-5-(methoxymethoxy)undec-1-en-6-yloxy](tert-butyl)diphenylsilane 
• 1585968-97-3 [(5S,6R)-5-(methoxymethoxy)undec-1-en-6-yloxy](tert-butyl)diphenylsilane 
• 128142-68-7 (S)-2-(tert-butyldiphenylsilyloxy)heptanal 

Relevant academic research and scientific papers

A High-Throughput Screening Method for the Directed Evolution of Hydroxynitrile Lyase towards Cyanohydrin Synthesis

Chiral cyanohydrins are useful intermediates in the pharmaceutical and agricultural industries. In nature, hydroxynitrile lyases (HNLs) are a kind of elegant tool for enantioselective hydrocyanation of carbonyl compounds. However, currently available methods for demonstrating hydrocyanation are still stalled at precise, but low-throughput, GC or HPLC analyses. Herein, we report a chromogenic high-throughput screening (HTS) method that is feasible for the cyanohydrin synthesis reaction. This method was highly anti-interference and sensitive, and could be used to directly profile the substrate scope of HNLs either in cell-free extract or fermentation clear broth. This HTS method was also validated by generating new variants of PcHNL5 that presented higher catalytic efficiency and stronger acidic tolerance in variant libraries.

Fusion of a Coiled-Coil Domain Facilitates the High-Level Production of Catalytically Active Enzyme Inclusion Bodies

The increasing number of biocatalytic reactions implemented in chemical synthesis routes raises the urgent need for large amounts of enzymes. Hence, new generic methods are required for their simple and cost-efficient production. Here, we describe a gener

Enantioselective cyanosilylation of aldehydes catalyzed by novel camphor derived Schiff bases-titanium(IV) complexes

Five tridentate Schiff bases have been prepared from (1R,2S,3R,4S)-3-amino- 1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol and salicylaldehydes. X-ray structure investigation revealed differences in their molecular conformation, and their titanium(IV) complexes

Chemoenzymatic asymmetric total synthesis of nonanolide (Z)-cytospolides D, E and their stereoisomers

Chemoenzymatic asymmetric total synthesis of the (Z)-isomer of the naturally occurring decanolide cytospolides D, E and six stereoisomers is reported. The main highlight of the synthetic venture involves ring-closing metathesis (RCM) reaction of a suitably functionalized ester compound, which was assembled by the Yamaguchi coupling of the required acid and alcohol fragments. The alcohol fragment was ac- cessed by two alternative chemoenzymatic processes, one being hydroxynitrile lyase mediated hydrocyanation, whereas lipase-catalyzed transesterification was the key sep in the second route. The acid fragment was constructed by an enantioselective enzymatic desymmetrization (EED) of prochiral 2-methyl-1,3-propanediol and Corey-Bakshi-Shibata (CBS) mediated stereoselective carbonyl reduction.

Chemoenzymatic Asymmetric Total Synthesis of Nonanolide (Z)-Cytospolides D, e and Their Stereoisomers

Chemoenzymatic asymmetric total synthesis of the (Z)-isomer of the naturally occurring decanolide cytospolides D, E and six stereoisomers is reported. The main highlight of the synthetic venture involves ring-closing metathesis (RCM) reaction of a suitably functionalized ester compound, which was assembled by the Yamaguchi coupling of the required acid and alcohol fragments. The alcohol fragment was accessed by two alternative chemoenzymatic processes, one being hydroxynitrile lyase mediated hydrocyanation, whereas lipase-catalyzed transesterification was the key sep in the second route. The acid fragment was constructed by an enantioselective enzymatic desymmetrization (EED) of prochiral 2-methyl-1,3-propanediol and Corey-Bakshi-Shibata (CBS) mediated stereoselective carbonyl reduction.

Hydroxynitrile lyase from Arabidopsis thaliana: Identification of reaction parameters for enantiopure cyanohydrin synthesis by pure and immobilized catalyst

The (R)-selective hydroxynitrile lyase from Arabidopsis thaliana (AtHNL) is a promising biocatalyst for the synthesis of a broad range of chiral cyanohydrins. However, the enantiomeric excess of the reaction is strongly compromised by a non-catalyzed side

α-Pinene-type chiral Schiff bases as tridentate ligands in asymmetric addition reactions

A group of tridentate Schiff bases derived from (+)-α-pinene were synthesized. The steric effects in the transition state, the importance of π-π stacking interactions as well as the electronic effects of aryl aldehydes according to Hammett constant values in the enantioselective addition of Et2Zn to aldehydes with the use of Schiff bases as chiral ligands are described. Also, a variety of aldehydes were cyanated using a catalyst prepared in situ from titanium tetraisopropoxide and chiral Schiff bases. The influence of a conjugated double-bond in the cyanation substrates on enantioselectivity was observed. The chemical structures of the chiral Schiff base-titanium alkoxide complexes are discussed based on their 1H and 13C NMR spectra. 3D models of the Zn2-complex catalyst and Ti-complex catalyst containing α-pinane-type Schiff bases based on X-ray diffraction experiments are postulated. The models presented were consistent with the reported chirality of the addition product and observed ee.

Enantioselective silylcyanation of aldehydes catalyzed by new chiral oxovanadium complex

Oxovanadium(V) complex 4 was prepared from VOSO4 and tridentate Schiff base ligand, which was prepared from substituted salicylaldehyde and inexpensive (S)-valine. Asymmetric silylcyanation of the aldehydes catalyzed by catalyst 4 afforded cyanohydrins with good enantioselectivities.

Dibutyltin dimethoxide-catalyzed cyano transfer to aldehydes and imines

A novel reaction involving cyano transfer from benzophenone cyanohydrin to aldehydes and imines was realized by using dibutyltin dimethoxide as a catalyst. Various cyanohydrins and α-amino nitriles were obtained in moderate to high yields by this reaction. Ketimines also showed remarkable reactivity as cyano acceptors under conventional reaction conditions. This catalytic reaction was further applied to a three-component condensation reaction of aldehydes, aniline, and benzophenone cyanohydrin in the presence of Drierite. Copyright

An R-selective hydroxynitrile lyase from Arabidopsis thaliana with an α/β-hydrolase fold

Folding and selectivity: The noncyanogenic plant Arabidopsis thaliana contains a new hydroxynitrile lyase, which was cloned and characterized. This enzyme is readily available form a recombinant source, has a broad range of substrates, and enantioselectively transforms aliphatic and aromatic aldehydes as well as ketones into the corresponding R-cyanohydrins. (Chemical Equation Presented).