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Literature summary for 4.2.1.92 extracted from

  • Jacopini, S.; Mariani, M.; de Caraffa, V.B.; Gambotti, C.; Vincenti, S.; Desjobert, J.M.; Muselli, A.; Costa, J.; Berti, L.; Maury, J.
    Olive recombinant hydroperoxide lyase, an efficient biocatalyst for synthesis of green leaf volatiles (2016), Appl. Biochem. Biotechnol., 179, 671-683 .
    View publication on PubMed
Search for more literature for 4.2.1.92

Application

Application Comment Organism
synthesis the recombinant 13-HPL enzyme is valuated as biocatalyst to produce C6-aldehydes Olea europaea

Cloned(Commentary)

Cloned (Comment) Organism
a cDNA encoding for olive HPL of Leccino variety is isolated from black olive fruits, cloned in pQE-30 expression vector, and expressed as His-tagged proteins in Escherichia coli strain M15. In order to improve the enzyme solubility, the chloroplast transit peptide is deleted Olea europaea

Protein Variants

Protein Variants Comment Organism
additional information the recombinant 13-HPL enzyme is assayed as biocatalyst to produce C6-aldehydes, optimization of the biotransformation conditions of (9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid and (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid into hexanal and (Z)-3-hexenal, respectively, to achieve the highest yields. The wild-type full-length enzyme acts more effectively on (9Z,11E,15Z)-(13S)-hydroperoxyoctadeca-9,11,15-trienoate and (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid than on the truncated enzyme lacking the chloroplast transit peptide Olea europaea

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.0431
-
 (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid pH 7.5, 25°C, recombinant full-length enzyme Olea europaea
0.04322
-
 (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid pH 7.5, 25°C, recombinant truncated enzyme Olea europaea
0.1528
-
 (9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid pH 7.5, 25°C, recombinant full-length enzyme Olea europaea
0.1739
-
 (9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid pH 7.5, 25°C, recombinant truncated enzyme Olea europaea

Localization

Localization Comment Organism GeneOntology No. Textmining
chloroplast envelope the enzyme contains a chloroplast transit peptide in its N-terminal end for targeting and insertion to the chloroplast envelope Olea europaea 9941
-

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid Olea europaea
-
 hexanal + 12-oxo-9-dodecenoic acid
-
 ?
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid Olea europaea
-
 (Z)-3-hexenal + 12-oxo-9-dodecenoic acid
-
 ?
additional information Olea europaea according to their specificity, HPLs can act on the 9- or 13-hydroperoxides of linoleic and linolenic acids (hydroperoxyoctadecadienoic acid (HPOD) and hydroperoxyoctadecatrienoic acid (HPOT)) and catalyze the cleavage of these hydroperoxides into C6- or C9-aldehydes and the C12- or C9-oxo-acids, respectively ?
-
 ?

Organism

Organism UniProt Comment Textmining
Olea europaea G8XQN2 Leccino variety
-

Purification (Commentary)

Purification (Comment) Organism
recombinant His-tagged full-length and truncated enzymes from Escherichia coli strain M15 by cobalt affinity chromatography Olea europaea

Source Tissue

Source Tissue Comment Organism Textmining
fruit black olives of the Leccino variety harvested at 20 weeks after flowering. Olive HPL is active in a range of pH between 6.0 and 8.0 with an optimal pH at 6.5 and an optimal production of C6 compounds performed at 20°C Olea europaea
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid
-
 Olea europaea hexanal + 12-oxo-9-dodecenoic acid
-
 ?
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid
-
 Olea europaea (Z)-3-hexenal + 12-oxo-9-dodecenoic acid
-
 ?
additional information according to their specificity, HPLs can act on the 9- or 13-hydroperoxides of linoleic and linolenic acids (hydroperoxyoctadecadienoic acid (HPOD) and hydroperoxyoctadecatrienoic acid (HPOT)) and catalyze the cleavage of these hydroperoxides into C6- or C9-aldehydes and the C12- or C9-oxo-acids, respectively Olea europaea ?
-
 ?
additional information the recombinant 13-HPL enzyme is assayed as biocatalyst to produce C6-aldehydes. Bioconversion of 13-hydroperoxides of linoleic and linolenic acids by recombinant enzyme with or without chloroplast targeting signal sequence, reaction products are identified and quantified using gas chromatography and mass spectrometry. Recombinant HPL enzyme with targeting sequence allows production of 5.61 mM hexanal and 4.39 mM (Z)-3-hexenal, corresponding to high conversion yields of 93.5% and 73%, respectively. The HPL enzyme without targeting sequence fails to obtain greater quantities of hexanal or (Z)-3-hexenal. No undesirable products are formed, and no isomerization of (Z)-3-hexenal in (E)-2-hexenal occurs Olea europaea ?
-
 ?

Subunits

Subunits Comment Organism
? x * 50000, about, recombinant enzyme with or without transit peptide, SDS-PAGE Olea europaea

Synonyms

Synonyms Comment Organism
13-HPL
-
 Olea europaea
13-hydroperoxide lyase
-
 Olea europaea
HPL
-
 Olea europaea
hydroperoxide lyase
-
 Olea europaea

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
25
-
 recombinant enzyme Olea europaea

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
17.89
-
 (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid pH 7.5, 25°C, recombinant truncated enzyme Olea europaea
26.38
-
 (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid pH 7.5, 25°C, recombinant full-length enzyme Olea europaea
402.62
-
 (9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid pH 7.5, 25°C, recombinant truncated enzyme Olea europaea
564.95
-
 (9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid pH 7.5, 25°C, recombinant full-length enzyme Olea europaea

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.5
-
 recombinant enzyme Olea europaea

pH Stability

pH Stability pH Stability Maximum Comment Organism
6.5 8 purified recombinant enzyme, over 80% activity remaining Olea europaea

General Information

General Information Comment Organism
evolution hydroperoxide lyases are classified in the cytochrome P450 family and more particularly in the two subfamilies CYP74B (13-HPL) and CYP74C (9-HPL and 9/13-HPL) Olea europaea
metabolism the enzyme is involved in the lipoxygenase (LOX) pathway Olea europaea
physiological function green leaf volatiles (GLVs) are the main contributors to the characteristic odor of plants known under the name of green note. GLVs are naturally produced through a metabolic pathway of the C18-polyunsaturated fatty acids named the lipoxygenase pathway. First, the lipoxygenase (LOX) catalyzes the oxygenation of linoleic and linolenic acids to form corresponding fatty acid hydroperoxides which are then cleaved by hydroperoxide lyase (HPL) to generate short-chain aldehydes and oxoacids. GLVs are widely used by various industries to improve food quality by restoring the fresh and fruity green odor or to add a touch of freshness to fragrances. The C6-aldehyde compounds are the main components (about 80 %) of the virgine olive oil flavor Olea europaea

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
413.9
-
 (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid pH 7.5, 25°C, recombinant truncated enzyme Olea europaea
612.1
-
 (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid pH 7.5, 25°C, recombinant full-length enzyme Olea europaea
2315.2
-
 (9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid pH 7.5, 25°C, recombinant truncated enzyme Olea europaea
3697.3
-
 (9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid pH 7.5, 25°C, recombinant full-length enzyme Olea europaea