superpathway of aromatic compound degradation via 2-hydroxypentadienoate

Marín M, Plumeier I, Pieper DH. Degradation of 2,3-dihydroxybenzoate by a novel meta-cleavage pathway. J Bacteriol. 2012 Aug;194(15):3851–60. PMID: 22609919; PMCID: PMC3416551.; Kasai D, Fujinami T, Abe T, Mase K, Katayama Y, Fukuda M, Masai E. Uncovering the protocatechuate 2,3-cleavage pathway genes. J Bacteriol. 2009 Nov;191(21):6758–68. PMID: 19717587; PMCID: PMC2795304.; Takenaka S, Sato T, Koshiya J, Murakami S, Aoki K. Gene cloning and characterization of a deaminase from the 4-amino-3-hydroxybenzoate-assimilating Bordetella sp. strain 10d. FEMS Microbiol Lett. 2009 Sep;298(1):93–8. doi: 10.1111/j.1574-6968.2009.01699.x. PMID: 19594622.; Harwood CS, Parales RE. The beta-ketoadipate pathway and the biology of self-identity. Annu Rev Microbiol. 1996;50():553–90. doi: 10.1146/annurev.micro.50.1.553. PMID: 8905091.; Kukor JJ, Olsen RH. Genetic organization and regulation of a meta cleavage pathway for catechols produced from catabolism of toluene, benzene, phenol, and cresols by Pseudomonas pickettii PKO1. J Bacteriol. 1991 Aug;173(15):4587–94. doi: 10.1128/jb.173.15.4587-4594.1991.; Menn FM, Zylstra GJ, Gibson DT. Location and sequence of the todF gene encoding 2-hydroxy-6-oxohepta-2,4-dienoate hydrolase in Pseudomonas putida F1. Gene. 1991 Jul 31;104(1):91–4. doi: 10.1016/0378-1119(91)90470-v. PMID: 1916282.; Kishore G, Sugumaran M, Vaidyanathan CS. Metabolism of DL-(+/-)-phenylalanine by Aspergillus niger. J Bacteriol. 1976 Oct;128(1):182–91. doi: 10.1128/jb.128.1.182-191.1976.; Wheelis ML, Stanier RY. The genetic control of dissimilatory pathways in Pseudomonas putida. Genetics. 1970 Oct;66(2):245–66. PMID: 5525301; PMCID: PMC1212492.

Metabolites

1,10-Phenanthroline

Formula: C12H8N2 (180.0687448)

CAS ID: 66-71-7

1,2-Naphthoquinone

Formula: C10H6O2 (158.0367776)

CAS ID: 524-42-5

2,3-Dihydroxytoluene

Formula: C7H8O2 (124.05242679999999)

CAS ID: 488-17-5

4-Hydroxybenzaldehyde

Formula: C7H6O2 (122.0367776)

CAS ID: 123-08-0

4-Hydroxybenzoate

Formula: C7H6O3 (138.03169259999999)

CAS ID: 99-96-7

4-Methylcatechol

Formula: C7H8O2 (124.05242679999999)

CAS ID: 452-86-8

8-Hydroxyquinoline

Formula: C9H7NO (145.0527612)

CAS ID: 148-24-3

Acetaldehyde

Formula: C2H4O (44.0262134)

CAS ID: 75-07-0

Aromatic aldehyde

Formula: C7H6O (106.0418626)

CAS ID: 100-52-7

Catechol

Formula: C6H6O2 (110.0367776)

CAS ID: 120-80-9

Cl-

Formula: Cl (34.968853)

CAS ID: 16887-00-6

CO

Formula: CO (27.994915)

CAS ID: 630-08-0

CO2

Formula: CO2 (43.98983)

CAS ID: 124-38-9

Cobalt ion

Formula: Co (58.933198)

CAS ID: 22541-53-3

Copper

Formula: Cu (62.929599)

CAS ID: 7440-50-8

Diphosphate

Formula: H4P2O7 (177.9432294)

CAS ID: 2466-09-3

Fe2+

Formula: Fe (55.934939)

CAS ID: 15438-31-0

Fe3+

Formula: Fe (55.934939)

CAS ID: 7439-89-6

Fluoride

Formula: F (18.9984032)

CAS ID: 7782-41-4

H+

Formula: H (1.0078246)

CAS ID: 12408-02-5

H2O

Formula: H2O (18.0105642)

CAS ID: 7732-18-5

Hydrogen cyanide

Formula: CHN (27.010898599999997)

CAS ID: 74-90-8

Iodide

Formula: I (126.904477)

CAS ID: 20461-54-5

L-Formylkynurenine

Formula: C11H12N2O4 (236.07970319999998)

CAS ID: 1022-31-7

Magnesium cation

Formula: Mg (23.98505)

CAS ID: 22537-22-0

Manganese(2+)

Formula: Mn (54.938046)

CAS ID: 7439-96-5

Mercury(2+)

Formula: Hg (201.970632)

CAS ID: 14302-87-5

N-Ethylmaleimide

Formula: C6H7NO2 (125.0476762)

CAS ID: 128-53-0

Naphthalene

Formula: C10H8 (128.0625968)

CAS ID: 91-20-3

Naphthalene-1,2-diol

Formula: C10H8O2 (160.0524268)

CAS ID: 574-00-5

Nickel(2+)

Formula: Ni (57.935347)

CAS ID: 14701-22-5

Oxygen

Formula: O2 (31.98983)

CAS ID: 7782-44-7

Potassium cation

Formula: K (38.963708)

CAS ID: 24203-36-9

Rubidium cation

Formula: Rb (84.9118)

CAS ID: 22537-38-8

Salicylaldehyde

Formula: C7H6O2 (122.0367776)

CAS ID: 90-02-8

Toluene

Formula: C7H8 (92.0625968)

CAS ID: 108-88-3

Toluene-cis-dihydrodiol

Formula: C7H10O2 (126.068076)

CAS ID: 41977-20-2

2,2'-Bipyridine

Formula: C10H8N2 (156.0687448)

CAS ID: 366-18-7

Salicylates

Formula: C7H5O3 (137.023868)

CAS ID: 63-36-5

4-aminobenzoate

Formula: C7H6NO2 (136.0398516)

CAS ID: 2906-28-7

benzoate

Formula: C7H5O2 (121.028953)

CAS ID: 766-76-7

formate

Formula: CHO2 (44.997654600000004)

CAS ID: 71-47-6

L-quinate

Formula: C7H11O6 (191.0555606)

CAS ID:

acetate

Formula: C2H3O2 (59.0133038)

CAS ID: 71-50-1

pyruvate

Formula: C3H3O3 (87.00821880000001)

CAS ID: 57-60-3

phenylglyoxylate

Formula: C8H5O3 (149.023868)

CAS ID:

3-hydroxybenzoate

Formula: C7H5O3 (137.023868)

CAS ID: 10476-50-3

shikimate

Formula: C7H9O5 (173.0449964)

CAS ID:

4-fluorobenzoate

Formula: C7H4FO2 (139.0195316)

CAS ID: 2365-27-7

anthranilate

Formula: C7H6NO2 (136.0398516)

CAS ID: 9031-59-8

nitrilotriacetate(3-)

Formula: C6H6NO6 (188.0195116)

CAS ID: 28528-44-1

NADPH(4-)

Formula: C21H26N7O17P3 (741.0598016)

CAS ID: 53-57-6

NAD(1-)

Formula: C21H26N7O14P2 (662.1012936000001)

CAS ID: 53-84-9

NADP(3-)

Formula: C21H25N7O17P3 (740.051977)

CAS ID: 53-59-8



Enzyme

EC Number name full name note
1.13.11.-
1.1.5.8 quinate/shikimate dehydrogenase (quinone) quinate:quinol 3-oxidoreductase
1.1.99.31 (S)-mandelate dehydrogenase (S)-2-hydroxy-2-phenylacetate:acceptor 2-oxidoreductase
1.13.11.2 catechol 2,3-dioxygenase catechol:oxygen 2,3-oxidoreductase (decyclizing)
1.14.12.1 anthranilate 1,2-dioxygenase (deaminating, decarboxylating) anthranilate,NAD(P)H:oxygen oxidoreductase (1,2-hydroxylating, deaminating, decarboxylating)
1.14.12.12 naphthalene 1,2-dioxygenase naphthalene,NADH:oxygen oxidoreductase (1,2-hydroxylating)
1.14.13.1 salicylate 1-monooxygenase salicylate,NADH:oxygen oxidoreductase (1-hydroxylating, decarboxylating)
1.14.13.2 4-hydroxybenzoate 3-monooxygenase 4-hydroxybenzoate,NADPH:oxygen oxidoreductase (3-hydroxylating)
1.18.1.3 ferredoxin-NAD+ reductase ferredoxin:NAD+ oxidoreductase
1.18.1.7 ferredoxin-NAD(P)+ reductase (naphthalene dioxygenase ferredoxin-specific) ferredoxin:NAD(P)+ oxidoreductase
1.2.1.28 benzaldehyde dehydrogenase (NAD+) benzaldehyde:NAD+ oxidoreductase
1.2.1.65 salicylaldehyde dehydrogenase salicylaldehyde:NAD+ oxidoreductase
1.2.1.7 benzaldehyde dehydrogenase (NADP+) benzaldehyde:NADP+ oxidoreductase
1.2.1.85 2-hydroxymuconate-6-semialdehyde dehydrogenase 2-hydroxymuconate-6-semialdehyde:NAD+ oxidoreductase
1.3.1.25 1,6-dihydroxycyclohexa-2,4-diene-1-carboxylate dehydrogenase (1R,6S)-1,6-dihydroxycyclohexa-2,4-diene-1-carboxylate:NAD+ oxidoreductase (decarboxylating)
3.7.1.25 2-hydroxy-6-oxohepta-2,4-dienoate hydrolase (2Z,4E)-2-hydroxy-6-oxohepta-2,4-dienoate acetylhydrolase
3.7.1.3 kynureninase L-kynurenine hydrolase
3.7.1.9 2-hydroxymuconate-6-semialdehyde hydrolase 2-hydroxymuconate-6-semialdehyde formylhydrolase
4.1.1.7 benzoylformate decarboxylase benzoylformate carboxy-lyase (benzaldehyde-forming)
4.1.1.77 2-oxo-3-hexenedioate decarboxylase (3E)-2-oxohex-3-enedioate carboxy-lyase (2-oxopent-4-enoate-forming)
4.1.2.45 trans-o-hydroxybenzylidenepyruvate hydratase-aldolase (3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoate hydro-lyase
4.1.3.39 4-hydroxy-2-oxovalerate aldolase 4-hydroxy-2-oxopentanoate pyruvate-lyase (acetaldehyde-forming)
4.2.1.10 3-dehydroquinate dehydratase 3-dehydroquinate hydro-lyase (3-dehydroshikimate-forming)
4.2.1.118 3-dehydroshikimate dehydratase 3-dehydroshikimate hydro-lyase
5.1.2.2 mandelate racemase mandelate racemase
5.3.2.6 2-hydroxymuconate tautomerase (2Z,4E)-2-hydroxyhexa-2,4-dienedioate keto-enol isomerase
5.99.1.4 2-hydroxychromene-2-carboxylate isomerase 2-hydroxy-2H-chromene-2-carboxylate-(3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoate isomerase


Proteins

Protein ID name full name
A5W4E9 todA Toluene 1,2-dioxygenase system ferredoxin--NAD(+) reductase component
O85673 antA Anthranilate 1,2-dioxygenase large subunit
O85674 antB Anthranilate 1,2-dioxygenase small subunit
O85675 antC Anthranilate 1,2-dioxygenase electron transfer component
P00438 pobA p-hydroxybenzoate hydroxylase
P06622 xylE Metapyrocatechase
P0A110 ndoB Naphthalene 1,2-dioxygenase system, large oxygenase component
P0A144 nahE Trans-O-hydroxybenzylidenepyruvate hydratase-aldolase
P0A391 nahF Salicylaldehyde dehydrogenase
P11444 mdlA Mandelate racemase
P13453 todE 3-methylcatechol 2,3-dioxygenase
P13859 todD Cis-toluene dihydrodiol dehydrogenase
P20906 mdlC Benzoylformate decarboxylase
P20932 mdlB (S)-mandelate dehydrogenase
P23099 xylX Toluate 1,2-dioxygenase subunit alpha
P23100 xylY Toluate 1,2-dioxygenase subunit beta
P23101 xylZ Toluate 1,2-dioxygenase electron transfer component
P23102 xylL 1,6-dihydroxycyclohexa-2,4-diene-1-carboxylate dehydrogenase
P23105 xylG 2-hydroxymuconic semialdehyde dehydrogenase
P23106 xylF 2-hydroxymuconate semialdehyde hydrolase
P23107 xylJ 2-hydroxypent-2,4-dienoate hydratase
P23133 todF 2-hydroxy-6-oxo-2,4-heptadienoate hydrolase
P23262 nahG Salicylate hydroxylase
P43503 xylC Benzaldehyde dehydrogenase [NAD(+)]
P49155 xylI 4-oxalocrotonate decarboxylase
P51018 todH 4-hydroxy-2-oxovalerate aldolase 1
P51019 xylK 4-hydroxy-2-oxovalerate aldolase
P83788 kynU Kynureninase
Q01468 xylH 2-hydroxymuconate tautomerase
Q43922 quiC 3-dehydroshikimate dehydratase
Q51948 nahD 2-hydroxychromene-2-carboxylate isomerase
Q52126 ndoR Naphthalene 1,2-dioxygenase system ferredoxin--NAD(P)(+), reductase component
Q59086 quiA Quinate/shikimate dehydrogenase (quinone)
Q59087 quiB Catabolic 3-dehydroquinate dehydratase
Q84DC3 mdlD NAD(P)-dependent benzaldehyde dehydrogenase