تفاعل #2198685

ord-c49d4255d3aa48fd8542304eeeeacce6

معادلة التفاعل

NC1=CC(=O)C=C(O)C1=O
2-amino-6-hydroxy-benzoquinone
N[C@@H]1CC(C(=O)O)=C[C@@H](O)[C@H]1O
aminoshikimate
O=C[C@H](O)[C@H](O)COP(=O)(O)O
D-erythrose-4-phosphate
N[C@@H]1CC(C(=O)O)=C[C@@H](O)[C@H]1O
aminoshikimate
N[C@H](CC(=O)C(=O)O)[C@H](O)[C@H](O)COP(=O)(O)O
3,4-dideoxy-4-amino-D-arabino-heptulosonic acid 7-phosphate
Nc1cc(O)cc(C(=O)O)c1
3-amino-5-hydroxy-benzoic acid
O=C[C@H](O)[C@H](O)COP(=O)(O)O
erythrose 4-phosphate
C=C(OP(=O)(O)O)C(=O)O
phosphoenolpyruvate
Nc1cc(O)cc(C(=O)O)c1
3-amino-5-hydroxy-benzoic acid
N[C@@H]1CC(C(=O)O)=C[C@@H](O)[C@H]1O
aminoshikimate
Nc1cc(O)cc(C(=O)O)c1O
3-amino-2,5-dihydroxy-benzoic acid
NC1=CC(=O)C=C(O)C1=O
2-amino-6-hydroxy-[1,4]-benzoquinone
O=C(O)C(=O)C[C@@H](O)[C@H](O)[C@H](O)COP(=O)(O)O
DAHP
Nc1cc(O)cc(O)c1O
6-amino-benzene-1,2,4-triol

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىprovided by primary metabolism biosynthetic pathways present in Micromonospora sp
  2. 2
    أخرى65) that catalyzes a decarboxylative oxidation reaction

الإجراء التجريبي

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).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07521222B2uspto-grants-2009_04