45789-64-8

Upstream product

• 16750-42-8 2-amino-2-phenylacetonitrile 

Downstream Products

• 700-63-0 (R)-phenylglycine amide 

Relevant academic research and scientific papers

High yield synthesis of d-phenylglycine and its derivatives by nitrilase mediated dynamic kinetic resolution in aqueous-1-octanol biphasic system

A strategy of nitrilase mediated dynamic kinetic resolution toward the synthesis of d-phenylglycine was developed, using aqueous-1-octanol biphasic system. Due to the efficient suppression of the decomposition of phenylglycinonitrile, a maximum yield of 81% is obtained. This result indicates that the nitrilase mediated dynamic kinetic resolution is a promising method toward the synthesis of d-phenylglycine and its derivatives.

Process Optimisation Studies and Aminonitrile Substrate Evaluation of Rhodococcus erythropolis SET1, A Nitrile Hydrolyzing Bacterium

A comprehensive series of optimization studies including pH, solvent and temperature were completed on the nitrile hydrolyzing Rhodococcus erythropolis bacterium SET1 with the substrate 3-hydroxybutyronitrile. These identified temperature of 25 °C and pH of 7 as the best conditions to retain enantioselectivity and activity. The effect of the addition of organic solvents to the biotransformation mixture was also determined. The results of the study suggested that SET1 is suitable for use in selected organo-aqueous media at specific ratios only. The functional group tolerance of the isolate with unprotected and protected β-aminonitriles, structural analogues of β-hydroxynitriles was also investigated with disappointingly poor isolated yields and selectivity obtained. The isolate was further evaluated with the α- aminonitrile phenylglycinonitrile generating acid in excellent yield and ee (>99 % (S) – isomer and 50 % yield). A series of pH studies with this substrate indicated pH 7 to be the optimum pH to avoid product and substrate degradation.

MANUFACTURING METHOD OF OPTICALLY ACTIVE AMINONITRILE COMPOUND AND MANUFACTURING METHOD OF OPTICALLY ACTIVE AMINO ACID

PROBLEM TO BE SOLVED: To provide a method for manufacturing an optically active aminonitrile compound with high purity suitable for manufacturing optically active amino acid and a method for manufacturing an optically active amino acid. SOLUTION: An optically active imine compound is obtained by condensing an optically active primary amine compound and a carbonyl compound in a solvent, a crystal of an optically active aminonitrile compound is deposited by adding hydrogen cyanide or a salt thereof to the imine compound in a solvent and asymmetric amplification for extremely enhancing diastereomer ratio thereof is conducted. The resulting aminonitrile compound with high optical purity is converted to optically active amino acid by known acid hydrolysis without deteriorating optical purity. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2017,JPOandINPIT

Stereoselective hydration of (RS)-phenylglycine nitrile by new whole cell biocatalysts

Five new bacterial isolates with stereoselective nitrile hydratase activity against (RS)-2-phenylpropionitrile and (RS)-phenylglycine nitrile were investigated. The permeabilized whole cell isolates selectively hydrate the (S)-enantiomer of phenylglycine nitrile with E values of 1.2-5.4. One isolate, which was identified as Pantoea endophytica, produced pure (S)-phenylglycine (>99% ee) as a result of hydrolysis of (S)-phenylglycine amide by an (S)-specific amidase. Surprisingly, in the hydrolysis of (RS)-phenylglycine nitrile, it was found that the (R)-amide was accumulated in excess (21% ee) despite the nitrile hydratase produced by Pantoea endophytica was (S)-selective. The synthesis of pure (R)-phenylglycine (>99% ee) was achieved in time course studies using another Pantoea sp. with (R)-selective amidase. In the case of Nocardioides sp. the intermediate product, (S)-phenylglycine amide, could be produced (52% ee) without its subsequent hydrolysis into the acid due to the apparent absence of any amidase activity.

A CONVENIENT METHOD FOR OPTICAL RESOLUTIONS VIA DIASTEREOISOMERIC SALT FORMATION

With the advantage of the method using two immiscible solvents and half-equivalent amount of the resolving agent, higher optical purity can be obtained than in cases of any other resolution via diastereoisomeric salt formation, besides it is a faster procedure for resolution of a new racemate as well.

Quantitative Approaches to Optical Resolution. Part 1. Resolution of DL-Phenylglycine Derivatives with (+)-Tartaric Acid

The results of 23 cases of resolution of DL-phenyldlycine derivatives (I) with (+)-tartaric acid in various solvents are investigated, using correlation analysis, as a function of the introduced racemic compounds and the solvent used.A procedure, combining three quantitative structure-activity relationship methods, i.e.Golender and Rozenblit's logico-structural approach with the Free-Wilson and Hansch analyses, resulted in statistically significant relationships.It is suggested that the solvent may exert two kinds of influence: (1) the higher the solvent polarity, the more likely the L-(I) salt to crystallise; (2) alcoholic mixtures, although being highly polar, favour the precipitation of the D-(I) salt rather than that of the L-(I) salt, probably due to a selective interaction with the diastereomers.As to the racemic compound, the relationships obtained are in accord with literature statements that resolution proceeds by a multiple interaction mechanism.

A QUANTITATIVE APPROACH TO OPTICAL RESOLUTION

Significant statistical relationships have been found between the parameters characterizing the results and circumstances of the resolutions of seventeen phenylglycine derivatives.The successful predictions given for the results of six indefendent resolutions prove the utility of these relationships.