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

HRID 2111503

반응식

HRID 2111503 반응식
[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]

참가 물질

9

반응물 8

HCID 1005PhosphoenolpyruvateHCID 122357Erythrose, 4-phosphate2회HCID 1271153-Amino-5-hydroxybenzoic acid2회HCID 1606473-Deoxy-D-arabino-heptulosonate-7-phosphateHCID 4436365-Deoxy-5-aminoshikimic acid3회HCID 219621272-Amino-6-hydroxy-[1,4]-benzoquinone2회HCID 219621363-Amino-2,5-dihydroxybenzoic acidHCID 56928076(4R,5S,6R)-4-amino-5,6-dihydroxy-2-oxo-7-phosphonooxy-heptanoic acid

생성물 1

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

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-c49d4255d3aa48fd8542304eeeeacce6
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07521222B2

연결된 노트

불러오는 중…