aliphatic (R)-hydroxynitrile lyase [EC:4.1.2.46]

PMID:9030531

Trummler K, Wajant H

Molecular cloning of acetone cyanohydrin lyase from flax (Linum usitatissimum). Definition of a novel class of hydroxynitrile lyases.

J Biol Chem 272:4770-4 (1997)
DOI:10.1074/jbc.272.8.4770

[ag:CAA70304]

(S)-hydroxynitrile lyase [EC:4.1.2.47]

PMID:8621461

Hasslacher M, Schall M, Hayn M, Griengl H, Kohlwein SD, Schwab H

Molecular cloning of the full-length cDNA of (S)-hydroxynitrile lyase from Hevea  brasiliensis. Functional expression in Escherichia coli and Saccharomyces cerevisiae and identification of an active site residue.

J Biol Chem 271:5884-91 (1996)
DOI:10.1074/jbc.271.10.5884

[ag:AAC49184]

PMID:8203915

Hughes J, Carvalho FJ, Hughes MA

Purification, characterization, and cloning of alpha-hydroxynitrile lyase from cassava (Manihot esculenta Crantz).

Arch Biochem Biophys 311:496-502 (1994)
DOI:10.1006/abbi.1994.1267

[ag:CAA82334]

Lyases;
Carbon-carbon lyases;
Aldehyde-lyases

(2R)-2-hydroxy-2-methylbutanenitrile butan-2-one-lyase (cyanide forming)

(2R)-2-hydroxy-2-methylbutanenitrile = cyanide + butan-2-one [RN:R09358]

R09358;
(other) R01553 R02811

(2R)-2-hydroxy-2-methylbutanenitrile [CPD:C18796]

The enzyme contains Zn2+ [1]. The enzyme catalyses the stereoselective synthesis of aliphatic (R)-cyanohydrins [1]. No activity towards mandelonitrile and 4-hydroxymandelonitrile [5]. Natural substrates for the (R)-oxynitrilase from Linum usitatissimum are acetone and butan-2-one, which are the building blocks of the cyanogen glycosides in Linum, linamarin and lotaustralin, or linustatin and neolinustatin, respectively [4].

EC 4.1.2.46 created 2011

1

Trummler, K., Roos, J., Schwaneberg, U., Effenberger, F., Forster, S., Pfizenmaier, K. and Wajant, H.

Expression of the Zn2+-containing hydroxynitrile lyase from flax (Linum usitatissimum) in Pichia pastoris- utilization of the recombinant enzyme for enzymatic analysis and site-directed mutagenesis.

Plant Sci. 139 (1998) 19-27.

2  [PMID:9030531]

Trummler K, Wajant H

Molecular cloning of acetone cyanohydrin lyase from flax (Linum usitatissimum). Definition of a novel class of hydroxynitrile lyases.

J. Biol. Chem. 272 (1997) 4770-4.

[ag:CAA70304]

3

Albrecht, J., Jansen, I.and Kula, M.R.

Improved purification of an (R)-oxynitrilase from Linum usitatissimum (flax) and investigation of the substrate range.

Biotechnol. Appl. Biochem. 17 (1993) 191-203.

4  [PMID:3377504]

Xu LL, Singh BK, Conn EE.

Purification and characterization of acetone cyanohydrin lyase from Linum usitatissimum.

Arch. Biochem. Biophys. 263 (1988) 256-63.

[ag:CAA70304]

5

Cabirol, F.L., Tan, P.L., Tay, B., Cheng, S., Hanefeld, U. and Sheldon, R.A.

Linum usitatissimum hydroxynitrile lyase cross-linked enzyme aggregates: a recyclable enantioselective catalyst.

Adv. Synth. Catal. 350 (2008) 2329-2338.

6

Breithaupt, H., Pohl, M., Bonigk, W., Heim, P., Schimz, K.-L. and Kula, M.-R.

Cloning and expression of (R)-hydroxynitrile lyase from Linum usitatissimum (flax).

J. Mol. Catal. B 6 (1999) 315-332.

Lyases;
Carbon-carbon lyases;
Aldehyde-lyases

(S)-cyanohydrin lyase (cyanide forming)

(1) an aliphatic (S)-hydroxynitrile = cyanide + an aliphatic aldehyde or ketone;
(2) an aromatic (S)-hydroxynitrile = cyanide + an aromatic aldehyde [RN:R09359]

R09359;
(other) R01409 R02811

aliphatic (S)-hydroxynitrile;
aromatic (S)-hydroxynitrile

Hydroxynitrile lyases catalyses the the cleavage of hydroxynitriles into cyanide and the corresponding aldehyde or ketone. In nature the liberation of cyanide serves as a defense mechanism against herbivores and microbial attack in plants. In vitro the enzymes from Manihot esculenta and Hevea brasiliensis accept a broad range of aliphatic and aromatic carbonyl compounds as substrates and catalyse the formation of (S)-hydroxynitriles [1,10].

EC 4.1.2.47 created 2011

1

Forster, S., Roos, J., Effenberger, F., Wajant, H. and Sprauer, A.

The first recombinant hydroxynitrile lyase and its application in the synthesis of (S)-cyanohydrins.

Angew. Chem. Int. Ed. 35 (1996) 437-439.

2  [PMID:12616635]

Buhler H, Effenberger F, Forster S, Roos J, Wajant H

Substrate specificity of mutants of the hydroxynitrile lyase from Manihot esculenta.

Chembiochem. 4 (2003) 211-6.

3  [PMID:18540112]

Semba H, Dobashi Y, Matsui T

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

Biosci. Biotechnol. Biochem. 72 (2008) 1457-63.

4  [PMID:19006143]

Avi M, Wiedner RM, Griengl H, Schwab H

Improvement of a stereoselective biocatalytic synthesis by substrate and enzyme engineering: 2-hydroxy-(4'-oxocyclohexyl)acetonitrile as the model.

Chemistry. 14 (2008) 11415-22.

5  [PMID:18204865]

von Langermann J, Guterl JK, Pohl M, Wajant H, Kragl U

Hydroxynitrile lyase catalyzed cyanohydrin synthesis at high pH-values.

Bioprocess. Biosyst. Eng. 31 (2008) 155-61.

6  [PMID:18524775]

Schmidt A, Gruber K, Kratky C, Lamzin VS

Atomic resolution crystal structures and quantum chemistry meet to reveal subtleties of hydroxynitrile lyase catalysis.

J. Biol. Chem. 283 (2008) 21827-36.

7  [PMID:17250917]

Gartler G, Kratky C, Gruber K

Structural determinants of the enantioselectivity of the hydroxynitrile lyase from Hevea brasiliensis.

J. Biotechnol. 129 (2007) 87-97.

8  [PMID:15299689]

Wagner UG, Schall M, Hasslacher M, Hayn M, Griengl H, Schwab H, Kratky C

Crystallization and preliminary X-ray diffraction studies of a hydroxynitrile lyase from Hevea brasiliensis.

Acta. Crystallogr. D. Biol. Crystallogr. 52 (1996) 591-3.

9

Schmidt, M., Herve, S., Klempier, N. and Griengl, H.

Preparation of optically active cyanohydrins using the (S)-hydroxynitrile lyase from Hevea brasiliensis.

Tetrahedron 52 (1996) 7833-7840.

10

Klempier, N. and Griengl, H.

Aliphatic (S)-cyanohydrins by enzyme catalyzed synthesis.

Tetrahedron Lett. 34 (1993) 4769-4772.