KEGG ENZYME: 4.1.2.46

ENZYME: 4.1.2.46

Entry

EC 4.1.2.46                 Enzyme

Name

aliphatic (R)-hydroxynitrile lyase;
(R)-HNL;
(R)-oxynitrilase;
(R)-hydroxynitrile lyase;
LuHNL

Class

Lyases;
Carbon-carbon lyases;
Aldehyde-lyases

Sysname

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

Reaction(IUBMB)

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

Reaction(KEGG)

R09358;
(other) R01553 R02811

Substrate

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

Product

cyanide [CPD:C00177];
butan-2-one [CPD:C02845]

Comment

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].

History

EC 4.1.2.46 created 2011

Pathway

ec00460

Cyanoamino acid metabolism

ec01100

Metabolic pathways

ec01110

Biosynthesis of secondary metabolites

Orthology

K14577

aliphatic (R)-hydroxynitrile lyase

Reference

Authors

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

Title

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.

Journal

Plant Sci 139:19-27 (1998)

Reference

2 [PMID:9030531]

Authors

Trummler K, Wajant H

Title

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

Journal

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

Sequence

[ag:CAA70304]

Reference

3 [PMID:8387315]

Authors

Albrecht J, Jansen I, Kula MR

Title

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

Journal

Biotechnol Appl Biochem 17 ( Pt 2):191-203 (1993)
DOI:10.1111/j.1470-8744.1993.tb00239.x

Reference

4 [PMID:3377504]

Authors

Xu LL, Singh BK, Conn EE

Title

Purification and characterization of acetone cyanohydrin lyase from Linum usitatissimum.

Journal

Arch Biochem Biophys 263:256-63 (1988)
DOI:10.1016/0003-9861(88)90634-0

Sequence

[ag:CAA70304]

Reference

Authors

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

Title

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

Journal

Adv Synth Catal 350:2329-2338 (2008)

Reference

Authors

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

Title

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

Journal

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

Other DBs

ExplorEnz - The Enzyme Database:

4.1.2.46

IUBMB Enzyme Nomenclature:

4.1.2.46

ExPASy - ENZYME nomenclature database:

4.1.2.46

BRENDA, the Enzyme Database:

4.1.2.46

DBGET integrated database retrieval system