This entry represents a group of alpha/beta-hydrolase fold-containing proteins mostly from plants, including methylesterase (MES) and hydroxynitrile lyase (HNL) from Arabidopsis. (Bacterial Hydroxynitrile_lyase are grouped in another family. HNLyase_Bact but are very closely related). There are at least 20 Arabidopsis MES members (AtMES1 - AtMES20). The catalytic triad Ser-His-Asp is conserved in 15 of these proteins. However, AtMES19 and AtMES20 lack part of the N-terminal or C-terminal region, respectively, and are therefore likely to be inactive enzymes. AtHNL catalyses the cleavage of cyanohydrins to yield hydrocyanic acid (HCN) and the respective carbonyl compound and are key enzymes in the process of cyanogenesis in plants. Interestingly, HNL homologue from Hevea brasiliensis, known as HbHNL, has opposite enantioselectivities and different reaction mechanisms compared to AtHNL. Cyanogenesis is a defense process of several thousand plant species. Hydroxynitrile lyase, a key enzyme of this process, cleaves a cyanohydrin into hydrocyanic acid and the corresponding aldehyde or ketone. The reverse reaction constitutes an important tool in biocatalysis. Hydroxynitrile lyase activity is performed by a wide variety of enzymes some resemble carboxypetidase (see sorghum hnl) other have completely unrelated sequences and structure and are more related to FAD-dependent oxidoreductases (GMC oxidoreductases family see structure 1JU2 Dreveny et al Structure 2001 9 803) or Zn dependent alcohol dehydrogenases and bacterial cupins. The present family also contains high affinity salicylic acid-binding protein 2 from plants required for innate immunity. Kumar et al.. The structure of Methylketone synthase 1 revealed a new active site for an alphabeta hydrolase: The nucleophile residue is Alanine located in a pentapeptide GHALG (Auldridge et al.). (a similar pentapeptide GHALD with histidine as nucleophile has been found in E. Coli RutD by Knapik et al in an un related family). PIRSF037175. This family also contains esterases such as Nicotiana tabacum (Common tobacco) salicylic acid-binding protein 2. Few mutations can convert one activity to the other (Padhi et al. Nedrud et al.). Some millipedes are able to exude toxic hydrogen cyanide as a defense, but hydroxynitril lyase from millipedes are not alpha/beta hydrolases
Interpro : IPR000073 Alpha\/beta hydrolase fold-1 , IPR045889 Methylesterase\/Alpha-hydroxynitrile lyase
PIRSF : PIRSF037175 esterase\/lyase
Pdoc : No Pdoc
Pfam : PF00561 Abhydrolase_1
Prints : No Print
EC Number : 4.1.2.47
Structures (57)
Genes Proteins in Hydroxynitrile_lyase family (219)
Fragments of genes in Hydroxynitrile_lyase family (30)
Structures in Hydroxynitrile_lyase family (57)Substrates in Hydroxynitrile_lyase family (17)
Inhibitors in Hydroxynitrile_lyase family (14)
Title : Evolution of a Catalytic Mechanism - Rauwerdink_2016_Mol.Biol.Evol_33_971 |
Author(s) : Rauwerdink A , Lunzer M , Devamani T , Jones B , Mooney J , Zhang ZJ , Xu JH , Kazlauskas RJ , Dean AM |
Ref : Molecular Biology Evolution , 33 :971 , 2016 |
PubMedID: 26681154 |
Gene_locus related to this paper: 9zzzz-5TDX , hevbr-hnl |
Title : Uncovering divergent evolution of alpha\/beta-hydrolases: a surprising residue substitution needed to convert hydroxynitrile lyase into an esterase - Nedrud_2014_Chem.Sci_5_4265 |
Author(s) : Nedrud DM , Lin H , Lopez G , Padhi SK , Legatt GA , Kazlauskas RJ |
Ref : Chem Sci , 5 :4265 , 2014 |
PubMedID: 25346843 |
Gene_locus related to this paper: hevbr-hnl , nicta-SABP2 |
Title : Emergent decarboxylase activity and attenuation of alpha\/beta-hydrolase activity during the evolution of methylketone biosynthesis in tomato - Auldridge_2012_Plant.Cell_24_1596 |
Author(s) : Auldridge ME , Guo Y , Austin MB , Ramsey J , Fridman E , Pichersky E , Noel JP |
Ref : Plant Cell , 24 :1596 , 2012 |
PubMedID: 22523203 |
Gene_locus related to this paper: solha-e0ycs2 |
Title : Hydroxynitrile lyases with alpha\/beta-hydrolase fold: two enzymes with almost identical 3D structures but opposite enantioselectivities and different reaction mechanisms - Andexer_2012_Chembiochem_13_1932 |
Author(s) : Andexer JN , Staunig N , Eggert T , Kratky C , Pohl M , Gruber K |
Ref : Chembiochem , 13 :1932 , 2012 |
PubMedID: 22851196 |
Gene_locus related to this paper: arath-HNL |
Title : Switching from an esterase to a hydroxynitrile lyase mechanism requires only two amino acid substitutions - Padhi_2010_Chem.Biol_17_863 |
Author(s) : Padhi SK , Fujii R , Legatt GA , Fossum SL , Berchtold R , Kazlauskas RJ |
Ref : Chemical Biology , 17 :863 , 2010 |
PubMedID: 20797615 |
Gene_locus related to this paper: hevbr-hnl , nicta-SABP2 |
Title : Uneven twins: comparison of two enantiocomplementary hydroxynitrile lyases with alpha\/beta-hydrolase fold - Guterl_2009_J.Biotechnol_141_166 |
Author(s) : Guterl JK , Andexer JN , Sehl T , von Langermann J , Frindi-Wosch I , Rosenkranz T , Fitter J , Gruber K , Kragl U , Eggert T , Pohl M |
Ref : J Biotechnol , 141 :166 , 2009 |
PubMedID: 19433222 |
Gene_locus related to this paper: arath-HNL , hevbr-hnl , manes-hnl |
Title : Inactive methyl indole-3-acetic acid ester can be hydrolyzed and activated by several esterases belonging to the AtMES esterase family of Arabidopsis - Yang_2008_Plant.Physiol_147_1034 |
Author(s) : Yang Y , Xu R , Ma CJ , Vlot AC , Klessig DF , Pichersky E |
Ref : Plant Physiol , 147 :1034 , 2008 |
PubMedID: 18467465 |
Gene_locus related to this paper: arath-MES17 , arath-AT4G16690 , arath-AT4G37150 , arath-MES6 , arath-MES7 , arath-MES3 , arath-MES1 , arath-MES18 , arath-MES10 , arath-MES19 |
Title : Reaction mechanism of hydroxynitrile lyases of the alpha\/beta-hydrolase superfamily: the three-dimensional structure of the transient enzyme-substrate complex certifies the crucial role of LYS236 - Gruber_2004_J.Biol.Chem_279_20501 |
Author(s) : Gruber K , Gartler G , Krammer B , Schwab H , Kratky C |
Ref : Journal of Biological Chemistry , 279 :20501 , 2004 |
PubMedID: 14998991 |
Gene_locus related to this paper: hevbr-hnl |
Title : High-affinity salicylic acid-binding protein 2 is required for plant innate immunity and has salicylic acid-stimulated lipase activity - Kumar_2003_Proc.Natl.Acad.Sci.U.S.A_100_16101 |
Author(s) : Kumar D , Klessig DF |
Ref : Proc Natl Acad Sci U S A , 100 :16101 , 2003 |
PubMedID: 14673096 |
Gene_locus related to this paper: nicta-SABP2 |
Title : Structure determinants of substrate specificity of hydroxynitrile lyase from Manihot esculenta - Lauble_2002_Protein.Sci_11_65 |
Author(s) : Lauble H , Miehlich B , Forster S , Kobler C , Wajant H , Effenberger F |
Ref : Protein Science , 11 :65 , 2002 |
PubMedID: 11742123 |
Gene_locus related to this paper: manes-hnl |
Title : 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 - Hasslacher_1996_J.Biol.Chem_271_5884 |
Author(s) : Hasslacher M , Schall M , Hayn M , Griengl H , Kohlwein SD , Schwab H |
Ref : Journal of Biological Chemistry , 271 :5884 , 1996 |
PubMedID: 8621461 |
Gene_locus related to this paper: hevbr-hnl |