KEGG ENZYME: 4.1.2.47

ENZYME: 4.1.2.47

Entry

EC 4.1.2.47                 Enzyme

Name

(S)-hydroxynitrile lyase;
(S)-cyanohydrin producing hydroxynitrile lyase;
(S)-oxynitrilase;
(S)-HbHNL;
(S)-MeHNL;
hydroxynitrile lyase;
oxynitrilase;
HbHNL;
MeHNL;
(S)-selective hydroxynitrile lyase;
(S)-cyanohydrin carbonyl-lyase (cyanide forming)

Class

Lyases;
Carbon-carbon lyases;
Aldehyde-lyases

Sysname

(S)-cyanohydrin lyase (cyanide-forming)

Reaction(IUBMB)

(1) an aliphatic (S)-hydroxynitrile = cyanide + an aliphatic aldehyde or ketone;
(2) an aromatic (S)-hydroxynitrile = cyanide + an aromatic aldehyde

Reaction(KEGG)

(other) R01409 R01553 R02811 R09359

Substrate

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

Product

cyanide [CPD:C01326];
aliphatic aldehyde;
aliphatic ketone;
aromatic aldehyde [CPD:C00193]

Comment

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].

History

EC 4.1.2.47 created 2011

Pathway

ec00460

Cyanoamino acid metabolism

ec01100

Metabolic pathways

ec01110

Biosynthesis of secondary metabolites

Orthology

K13033

(S)-hydroxynitrile lyase

Genes

HBR:

110640545

MESC:

110630413

MOF:

131160111

Reference

Authors

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

Title

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

Journal

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

Reference

2 [PMID:12616635]

Authors

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

Title

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

Journal

Chembiochem 4:211-6 (2003)
DOI:10.1002/cbic.200390033

Reference

3 [PMID:18540112]

Authors

Semba H, Dobashi Y, Matsui T

Title

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

Journal

Biosci Biotechnol Biochem 72:1457-63 (2008)
DOI:10.1271/bbb.70765

Reference

4 [PMID:19006143]

Authors

Avi M, Wiedner RM, Griengl H, Schwab H

Title

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

Journal

Chemistry 14:11415-22 (2008)
DOI:10.1002/chem.200800609

Reference

5 [PMID:18204865]

Authors

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

Title

Hydroxynitrile lyase catalyzed cyanohydrin synthesis at high pH-values.

Journal

Bioprocess Biosyst Eng 31:155-61 (2008)
DOI:10.1007/s00449-008-0198-4

Reference

6 [PMID:18524775]

Authors

Schmidt A, Gruber K, Kratky C, Lamzin VS

Title

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

Journal

J Biol Chem 283:21827-36 (2008)
DOI:10.1074/jbc.M801056200

Reference

7 [PMID:17250917]

Authors

Gartler G, Kratky C, Gruber K

Title

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

Journal

J Biotechnol 129:87-97 (2007)
DOI:10.1016/j.jbiotec.2006.12.009

Reference

8 [PMID:15299689]

Authors

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

Title

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

Journal

Acta Crystallogr D Biol Crystallogr 52:591-3 (1996)
DOI:10.1107/S0907444995016830

Reference

Authors

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

Title

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

Journal

Tetrahedron 52:7833-7840 (1996)

Reference

Authors

Klempier, N. and Griengl, H.

Title

Aliphatic (S)-cyanohydrins by enzyme catalyzed synthesis.

Journal

Tetrahedron Lett 34:4769-4772 (1993)

Other DBs

ExplorEnz - The Enzyme Database:

4.1.2.47

IUBMB Enzyme Nomenclature:

4.1.2.47

ExPASy - ENZYME nomenclature database:

4.1.2.47

BRENDA, the Enzyme Database:

4.1.2.47

DBGET integrated database retrieval system