158705-89-6

Upstream product

• 6309-18-8 2-(3,4-dimethoxyphenyl)-2-hydroxyacetonitrile 
• 74-90-8 hydrogen cyanide 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 151-50-8 potassium cyanide 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 

Downstream Products

• 158705-92-1 (1S,2R)-(-)-2-(tert-butyldiphenylsilyloxy)-2-(3,4-dimethoxyphenyl)-phenylethylamine 
• 158705-93-2 (1'S,2'R)-(-)-N-<2-(tert-butyldiphenylsilyloxy)-2-(3,4-dimethoxyphenyl)-1-phenylethyl>acetamide 
• 158705-94-3 (3S,4R)-(-)-4-(tert-butyldiphenylsilyloxy)-6,7-dimethoxy-1-methyl-3-phenyl-3,4-dihydroisoquinoline 
• 158705-96-5 (1R,3S,4R)-(+)-6,7-dimethoxy-4-hydroxy-1-methyl-3-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 158705-95-4 (3S,4R)-(+)-6,7-dimethoxy-4-hydroxy-1-methyl-3-phenyl-3,4-dihydroisoquinoline 
• 158666-69-4 (R)-(-)-2-(tert-butyldiphenylsilyloxy)-2-(3,4-di-methoxyphenyl)acetonitrile 

Relevant academic research and scientific papers

Novel (R)-oxynitrilase sources for the synthesis of (R)-cyanohydrins in diisopropyl ether

Apple, apricot, cherry and plum meal were prepared from the seeds or kernels of mature garden fruits. The preparations as well as almond meal were used as the source of (R)-oxynitrilase for the synthesis of aliphatic and aromatic cyanohydrins in diisoprop

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.

Structure-Guided Tuning of a Hydroxynitrile Lyase to Accept Rigid Pharmaco Aldehydes

The chiral vicinal C-O/C-N bifunctional groups generated from enzymatic hydrocyanation represents a useful methodology. However, construction of the pharmacophore of β2-adrenoreceptor agonists with this method remains a great challenge because of complete racemization of the benzylic alcohol during deprotection of the acetal groups. In this study, structure-guided redesign of a hydroxynitrile lyase originating from Prunus communis (PcHNL5) enables a highly enantioselective hydrocyanation of rigid benzo-ketal aldehyde which was proved to be resistant against racemization during the deprotection step, with dramatically improved productivity (>95% conversion vs 2-adrenoreceptor agonist, in an optically pure form (>99% ee) with an overall yield of 54%, which is the highest value reported.

A new (R)-hydroxynitrile lyase from Prunus mume: Asymmetric synthesis of cyanohydrins

A new hydroxynitrile lyase (HNL) was isolated from the seed of Japanese apricot (Prunus mume). The enzyme has similar properties with HNL isolated from other Prunus species and is FAD containing enzyme. It accepts a large number of unnatural substrates (benzaldehyde and its variant) for the addition of HCN to produce the corresponding cyanohydrins in excellent optical and chemical yields. A new HPLC based enantioselective assay technique was developed for the enzyme, which promotes the addition of KCN to benzaldehyde in a buffered solution (pH=4.5).

(R)- and (S)-cyanohydrins using oxynitrilases in whole cells

Almond meal and Sorghum bicolor shoots were used as the sources of oxynitrilases for the preparation of a number (R)- and (S)-arylcyanohydrins, respectively, from the corresponding aldehydes in diisopropyl ether. Two different in situ methods were used to introduce hydrogen cyanide into the reaction mixture. In method 1, acetone cyanohydrin decomposes enzymatically and/or chemically to hydrogen cyanide. In method 2, hydrogen cyanide freely evaporates from a solution in diisopropyl ether from one compartment of the reaction vessel and ends up to the other where it dissolves into the reaction mixture.

A Simple Enzymatic Synthesis of (3S,4R)-(+)-4-Hydroxy-3-phenyltetrahydroisoquinolines

An efficient versatile method is presented for the stereospecific synthesis of (+)-4-hydroxy-3-phenyltetrahydroisoquinolines 11 and 12 using (R)-arylcyanohydrins as the chiral starting material.From this asymmetric core, the synthetic process proceeds wit