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

HRID 2211595

反応式

HRID 2211595 の反応式
[NH2:1][C:2]1[C:3](=[O:10])[C:4]([OH:9])=[CH:5][C:6](=[O:8])[CH:7]=1.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]

参加物

9

反応物 8

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

生成物 1

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

実験手順

Biosynthesis of the 2-amino-6-hydroxy-benzoquinone component of the compound of Formula II, requires components derived from the aminoshikimate pathway. FIG. 14b 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. 14b).

後処理

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

出典と根拠

ORDレコード
ord-be0d67a550cf4bdd8e6f5dea28caae36
出典データセット
uspto-grants-2006_09
特許番号
US07101872B2

関連ノート

読み込み中…