Phosphoenolpyruvate → 6-Amino-benzene-1,2,4-triol

HRID 1593358

Reaction equation

HRID 1593358 reaction equation
[NH2:1][C:2]1[C:3](=[O:10])[C:4]([OH:9])=[CH:5][C:6](=[O:8])[CH:7]=1.C(C1C(=O)C2=C3C=CC=CC3=CN=NC2=CC=1)C=C(CCC=C(CCC=C(C)C)C)C.C1C(C(O)=O)=C[C@@H](O)[C@@H](O)[C@@H]1N.P(OC[C@@H](O)[C@@H](O)C=O)(O)(O)=O.C(C(C(O)=O)=O)[C@@H](O)[C@H](O)[C@H](O)COP(O)(O)=O.P(OC[C@@H](O)[C@@H](O)[C@H](N)CC(=O)C(O)=O)(O)(O)=O.C=C(OP(O)(O)=O)C(O)=O.NC1C=C(C=C(O)C=1)C(O)=O.NC1C(O)=C(C=C(O)C=1)C(O)=O>>[NH2:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([OH:9])[C:3]=1[OH:10]

Participants

10

Reactant 9

HCID 1005PhosphoenolpyruvateHCID 122357Erythrose, 4-phosphate2×HCID 1271153-Amino-5-hydroxybenzoic acid2×HCID 1606473-Deoxy-D-arabino-heptulosonate-7-phosphateHCID 4436365-Deoxy-5-aminoshikimic acid3×HCID 219621272-Amino-6-hydroxy-[1,4]-benzoquinone2×HCID 219621363-Amino-2,5-dihydroxybenzoic acidHCID 56928076(4R,5S,6R)-4-amino-5,6-dihydroxy-2-oxo-7-phosphonooxy-heptanoic acidHCID 86606861Farnesyl dibenzodiazepinone

Product 1

HCID 219621356-Amino-benzene-1,2,4-triol

Procedure

Biosynthesis of the 2-amino-6-hydroxy-benzoquinone component of the farnesyl dibenzodiazepinone, requires components derived from the aminoshikimate pathway. FIG. 7 depicts the series of enzymatic reactions involved in the biosynthesis of this constituent. ORF 21 (ALDB) (SEQ ID NO: 42) resembles aldolases involved in the generation of precursors of D-erythrose-4-phosphate which is part of the aminoshikimate pathway used for the generation of 2-amino-6-hydroxy-[1,4]-benzoquinone. ORF 33 (DAHP) (SEQ ID NO: 67) catalyzes the initial step in the aminoshikimate pathway that corresponds to the formation of 3,4-dideoxy-4-amino-D-arabino-heptulosonic acid 7-phosphate (amino DAHP) from phosphoenolpyruvate (PEP) and erythrose 4-phosphate (E-4Ph). Subsequent reactions leading to 3-amino-5-hydroxy-benzoic acid are catalyzed by enzymes provided by primary metabolism biosynthetic pathways present in Micromonospora sp. strain 046-ECO11. ORF 25 (HOXV) (SEQ ID NO: 50) hydroxylates 3-amino-5-hydroxy-benzoic acid at position 2, generating 3-amino-2,5-dihydroxy-benzoic acid. This intermediate is further modified by ORF 32 (HOYH) (SEQ ID NO: 65) that catalyzes a decarboxylative oxidation reaction yielding 6-amino-benzene-1,2,4-triol. A final oxidation reaction is performed by ORF 16 (OXDS) (SEQ ID NO: 32) yielding 2-amino-6-hydroxy-[1,4]-benzoquinone (FIG. 7).

Workup

  1. customprovided by primary metabolism biosynthetic pathways present in Micromonospora sp
  2. custom65) that catalyzes a decarboxylative oxidation reaction

Sources & evidence

ORD record
ord-7e851f99feea4dd49f5e1945bf4c8c6e
Source dataset
uspto-grants-2007_11
Patent number
US07297524B2

Linked notes

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