KEGG   ENZYME: 4.1.2.47Help
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
BRITE hierarchy
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 [RN:R09359]
Reaction(KEGG)
R09359;
(other) R01409 R02811
Show
Substrate
aliphatic (S)-hydroxynitrile;
aromatic (S)-hydroxynitrile
Product
cyanide [CPD:C00177];
aliphatic aldehyde;
ketone [CPD:C01450];
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
Cyanoamino acid metabolism
Metabolic pathways
Biosynthesis of secondary metabolites
Orthology
K13033  
(S)-hydroxynitrile lyase
Reference
1
  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 (1996) 437-439.
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 (2003) 211-6.
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 (2008) 1457-63.
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 (2008) 11415-22.
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 (2008) 155-61.
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 (2008) 21827-36.
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 (2007) 87-97.
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 (1996) 591-3.
Reference
9
  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 (1996) 7833-7840.
Reference
10
  Authors
Klempier, N. and Griengl, H.
  Title
Aliphatic (S)-cyanohydrins by enzyme catalyzed synthesis.
  Journal
Tetrahedron Lett. 34 (1993) 4769-4772.
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 

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