EC Number | Cloned (Comment) | Organism |
---|---|---|
1.3.1.77 | gene BAN, overexpression of the enzyme in Medicago truncatula hairy roots. Recombinant enzyme ANR does not generate epicatechin from epicatechin-cysteine conjugate in hairy roots | Medicago truncatula |
1.17.1.3 | gene lar, overexpression of the enzyme in Medicago truncatula hairy roots, conversion of 4beta-(S-cysteinyl)-epicatechin to epicatechin by recombinant LAR | Medicago truncatula |
EC Number | Protein Variants | Comment | Organism |
---|---|---|---|
1.3.1.77 | additional information | construction of Tnt1 insertion mutants of gene ANR, two mutants are isolated with Tnt1 insertions in the third and sixth exons, respectively, leading to loss of function of ANR, which gives large reductions in both soluble and insoluble proanthocyanidins in seeds compared to wild-type, low amounts of epicatechin and its 3'-O-glucoside in the anr-1 mutant. The seeds of anr mutants are darkred resulting from redirected metabolic flow from anthocyanidin to anthocyanin. The lar-1/anr-1 double mutant displays the same seed colour as the anr-1 mutant. The anr mutant seeds contain leucocyandin for catechin production, but no substrate for epicatechin production | Medicago truncatula |
1.17.1.3 | K143G | no activity with authentic 4beta-(S-cysteinyl)-epicatechin with recombinant mutant LAR | Medicago truncatula |
1.17.1.3 | additional information | a lar-1/anr-1 double mutant displays darkred colour resulting from redirected metabolic flow from anthocyanidin to anthocyanin | Medicago truncatula |
EC Number | Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
---|---|---|---|---|---|---|---|
1.3.1.77 | cyanidin + 2 NADPH + H+ | Medicago truncatula | - |
(2R,3R)-epicatechin + 2 NADP+ | ? | ? | |
1.3.1.77 | cyanidin + 2 NADPH + H+ | Medicago truncatula ecotype R108 | - |
(2R,3R)-epicatechin + 2 NADP+ | ? | ? | |
1.3.1.77 | additional information | Medicago truncatula | recombinant enzyme ANR does not generate epicatechin from epicatechin-cysteine conjugate in hairy roots | ? | - |
? | |
1.3.1.77 | additional information | Medicago truncatula ecotype R108 | recombinant enzyme ANR does not generate epicatechin from epicatechin-cysteine conjugate in hairy roots | ? | - |
? | |
1.17.1.3 | 2,3-trans-3,4-cis-leucocyanidin + NADPH + H+ | Medicago truncatula | - |
(2R,3S)-catechin + NADP+ + H2O | - |
? | |
1.17.1.3 | 2,3-trans-3,4-cis-leucocyanidin + NADPH + H+ | Medicago truncatula ecotype R108 | - |
(2R,3S)-catechin + NADP+ + H2O | - |
? | |
1.17.1.3 | 4beta-(S-cysteinyl)-epicatechin + NADPH + H+ | Medicago truncatula | enzyme LAR generates epicatechin from epicatechin-cysteine conjugate in an NADPH-dependent manner in hairy roots. 4beta-(S-Cysteinyl)-epicatechin provides the extension unit during procyanidin polymerization | epicatechin + cysteine + NADP+ | - |
? | |
1.17.1.3 | 4beta-(S-cysteinyl)-epicatechin + NADPH + H+ | Medicago truncatula ecotype R108 | enzyme LAR generates epicatechin from epicatechin-cysteine conjugate in an NADPH-dependent manner in hairy roots. 4beta-(S-Cysteinyl)-epicatechin provides the extension unit during procyanidin polymerization | epicatechin + cysteine + NADP+ | - |
? |
EC Number | Organism | UniProt | Comment | Textmining |
---|---|---|---|---|
1.3.1.77 | Medicago truncatula | Q84XT1 | - |
- |
1.3.1.77 | Medicago truncatula ecotype R108 | Q84XT1 | - |
- |
1.17.1.3 | Medicago truncatula | Q3KN75 | - |
- |
1.17.1.3 | Medicago truncatula ecotype R108 | Q3KN75 | - |
- |
EC Number | Source Tissue | Comment | Organism | Textmining |
---|---|---|---|---|
1.3.1.77 | hairy root | - |
Medicago truncatula | - |
1.3.1.77 | seed coat | - |
Medicago truncatula | - |
1.17.1.3 | seed coat | - |
Medicago truncatula | - |
EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
---|---|---|---|---|---|---|---|
1.3.1.77 | cyanidin + 2 NADPH + H+ | - |
Medicago truncatula | (2R,3R)-epicatechin + 2 NADP+ | ? | ? | |
1.3.1.77 | cyanidin + 2 NADPH + H+ | - |
Medicago truncatula ecotype R108 | (2R,3R)-epicatechin + 2 NADP+ | ? | ? | |
1.3.1.77 | additional information | recombinant enzyme ANR does not generate epicatechin from epicatechin-cysteine conjugate in hairy roots | Medicago truncatula | ? | - |
? | |
1.3.1.77 | additional information | recombinant enzyme ANR does not generate epicatechin from epicatechin-cysteine conjugate in hairy roots | Medicago truncatula ecotype R108 | ? | - |
? | |
1.17.1.3 | 2,3-trans-3,4-cis-leucocyanidin + NADPH + H+ | - |
Medicago truncatula | (2R,3S)-catechin + NADP+ + H2O | - |
? | |
1.17.1.3 | 2,3-trans-3,4-cis-leucocyanidin + NADPH + H+ | - |
Medicago truncatula ecotype R108 | (2R,3S)-catechin + NADP+ + H2O | - |
? | |
1.17.1.3 | 4beta-(S-cysteinyl)-epicatechin + NADPH + H+ | enzyme LAR generates epicatechin from epicatechin-cysteine conjugate in an NADPH-dependent manner in hairy roots. 4beta-(S-Cysteinyl)-epicatechin provides the extension unit during procyanidin polymerization | Medicago truncatula | epicatechin + cysteine + NADP+ | - |
? | |
1.17.1.3 | 4beta-(S-cysteinyl)-epicatechin + NADPH + H+ | enzyme LAR generates epicatechin from epicatechin-cysteine conjugate in an NADPH-dependent manner | Medicago truncatula | epicatechin + cysteine + NADP+ | - |
? | |
1.17.1.3 | 4beta-(S-cysteinyl)-epicatechin + NADPH + H+ | enzyme LAR generates epicatechin from epicatechin-cysteine conjugate in an NADPH-dependent manner in hairy roots. 4beta-(S-Cysteinyl)-epicatechin provides the extension unit during procyanidin polymerization | Medicago truncatula ecotype R108 | epicatechin + cysteine + NADP+ | - |
? | |
1.17.1.3 | 4beta-(S-cysteinyl)-epicatechin + NADPH + H+ | enzyme LAR generates epicatechin from epicatechin-cysteine conjugate in an NADPH-dependent manner | Medicago truncatula ecotype R108 | epicatechin + cysteine + NADP+ | - |
? |
EC Number | Synonyms | Comment | Organism |
---|---|---|---|
1.3.1.77 | ANR | - |
Medicago truncatula |
1.3.1.77 | BAN | - |
Medicago truncatula |
1.17.1.3 | LAR | - |
Medicago truncatula |
1.17.1.3 | MtLAR | - |
Medicago truncatula |
EC Number | Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
---|---|---|---|---|
1.17.1.3 | 22 | - |
assay at room temperature | Medicago truncatula |
EC Number | pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
---|---|---|---|---|
1.17.1.3 | 7 | - |
assay at | Medicago truncatula |
EC Number | Cofactor | Comment | Organism | Structure |
---|---|---|---|---|
1.3.1.77 | NADPH | - |
Medicago truncatula | |
1.17.1.3 | NADPH | - |
Medicago truncatula |
EC Number | Organism | Comment | Expression |
---|---|---|---|
1.3.1.77 | Medicago truncatula | overexpression of the myeloblastosis (MYB)14 or MYB5 transcription factors induces proanthocyanidin biosynthesis in hairy roots, ANR is highly induced in MYB5 overexpressing hairy roots | up |
1.17.1.3 | Medicago truncatula | overexpression of the myeloblastosis (MYB)14 or MYB5 transcription factors induces proanthocyanidin biosynthesis in hairy roots, LAR is induced in MYB5 overexpressing hairy roots | up |
EC Number | General Information | Comment | Organism |
---|---|---|---|
1.3.1.77 | malfunction | loss of function ANR mutants show large reductions in both soluble and insoluble proanthocyanidins in seeds compared to wild-type, as well as low amounts of epicatechin and its 3'-O-glucoside in the anr-1 mutant. The seeds of anr mutants are darkred resulting from redirected metabolic flow from anthocyanidin to anthocyanin | Medicago truncatula |
1.17.1.3 | metabolism | flavan-3-ols are synthesized through the flavonoid pathway via leucoanthocyanidin and anthocyanidin. Leucoanthocyanidin can be converted to (+)-flavan-3-ol, e.g. (+)-catechin, by leucoanthocyanidin reductase (LAR) or to anthocyanidin by anthocyanidin synthase (ANS) | Medicago truncatula |
1.17.1.3 | additional information | molecular modelling and molecular docking of epicatechin-cysteine to MtLAR, based on the crystal structure of Vitis vinifera LAR | Medicago truncatula |
1.17.1.3 | physiological function | role for leucoanthocyanidin reductase in the extension of proanthocyanidins. Monomeric flavan-3-ols do not dimerize in autopolymerization assays, whereas procyanidin B2 oligomerizes, either alone or with monomeric flavan-3-ols, suggesting that formation of epicatechin carbocation is a crucial step for proanthocyanidin assembly | Medicago truncatula |