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Chemical Compound Review:

Mandelonitrile 2-hydroxy-2-phenyl- ethanenitrile

Synonyms: CCRIS 4656, LS-193, CHEBI:16910, NSC-77668, AC1L1VVW, ...

Ageez, A. et al., Hickel, A. et al., Lai, L.B. et al., Kuroki, G.W. et al., Yamamoto, K. et al., et al.

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Disease relevance of Phenylglycolonitrile

Production of R-(-)-mandelic acid from mandelonitrile by Alcaligenes faecalis ATCC 8750 [1].
(R)-mandelic acid was produced from racemic mandelonitrile using free and immobilized cells of Pseudomonas putida MTCC 5110 harbouring a stereoselective nitrilase [2].

High impact information on Phenylglycolonitrile

A mandelonitrile lyase (EC 4.1.2.10) that catalyzes the dissociation of (S)-(-)-mandelonitrile to benzaldehyde and hydrogen cyanide has been purified to apparent homogeneity from leaves of Ximenia americana L [3].
The observed remote stereorecognition is surprising because this nitrilase shows no enantioselectivity for the hydrolysis of alpha-hydroxy nitriles such as mandelonitrile [4].
A. faecalis ATCC 8750 has an R-enantioselective nitrilase for mandelonitrile and an amidase for mandelamide [1].
Faster reaction rate achieved with this nitrilase for mandelonitrile hydrolysis was possibly due to the low activation energy required by the protein [5].
For the mandelonitrile-cleavage reaction at ambient temperature, p-Hnl follows Michaelis-Menten kinetics at the interface with a Michaelis constant of 14.4 mM and a specific activity close that for the bulk aqueous phase [6].

Associations of Phenylglycolonitrile with other chemical compounds

When L-picein hydrolysis was monitored at 320 nm and prunasin at 282 nm, the molar absorption coefficients determined for their products, namely piceol and mandelonitrile, were 3200 and 1360 M-1 cm-1, respectively [7].
Steady-state kinetic parameters for cleavage and synthesis of mandelonitrile and vanillin cyanohydrin were determined at pH 5.5 which is near the pH optimum of the enzyme [8].

Gene context of Phenylglycolonitrile

These five cDNAs are predicted to encode a mandelonitrile lyase protein (SlMDL1), a strictosidine synthase protein (SlSs), a glycosyl hydrolase 17 protein (SlGh17), a proline-rich protein APG precursor (SlAPG), and a chalcone-synthase-like protein (SlChs) [9].

Analytical, diagnostic and therapeutic context of Phenylglycolonitrile

Crystallization and preliminary X-ray diffraction studies of mandelonitrile lyase from almonds [10].

References

Production of R-(-)-mandelic acid from mandelonitrile by Alcaligenes faecalis ATCC 8750. Yamamoto, K., Oishi, K., Fujimatsu, I., Komatsu, K. Appl. Environ. Microbiol. (1991) [Pubmed]
Enhancing the catalytic potential of nitrilase from Pseudomonas putida for stereoselective nitrile hydrolysis. Banerjee, A., Kaul, P., Banerjee, U.C. Appl. Microbiol. Biotechnol. (2006) [Pubmed]
Mandelonitrile lyase from Ximenia americana L.: stereospecificity and lack of flavin prosthetic group. Kuroki, G.W., Conn, E.E. Proc. Natl. Acad. Sci. U.S.A. (1989) [Pubmed]
Unexpected Stereorecognition in Nitrilase-Catalyzed Hydrolysis of beta-Hydroxy Nitriles. Kamila, S., Zhu, D., Biehl, E.R., Hua, L. Org. Lett. (2006) [Pubmed]
Purification and characterization of an enantioselective arylacetonitrilase from Pseudomonas putida. Banerjee, A., Kaul, P., Banerjee, U.C. Arch. Microbiol. (2006) [Pubmed]
Hydroxynitrile lyase at the diisopropyl ether/water interface: evidence for interfacial enzyme activity. Hickel, A., Radke, C.J., Blanch, H.W. Biotechnol. Bioeng. (1999) [Pubmed]
Continuous spectrophotometric assays for beta-glucosidases acting on the plant glucosides L-picein and prunasin. Lai, L.B., Gopalan, V., Glew, R.H. Anal. Biochem. (1992) [Pubmed]
Studies on the kinetics of cyanohydrin synthesis and cleavage by the the flavoenzyme oxynitrilase. Jorns, M.S. Biochim. Biophys. Acta (1980) [Pubmed]
Male-fertility genes expressed in male flower buds of Silene latifolia include homologs of anther-specific genes. Ageez, A., Kazama, Y., Sugiyama, R., Kawano, S. Genes Genet. Syst. (2005) [Pubmed]
Crystallization and preliminary X-ray diffraction studies of mandelonitrile lyase from almonds. Lauble, H., Müller, K., Schindelin, H., Förster, S., Effenberger, F. Proteins (1994) [Pubmed]

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