Reaktion #1680540

ord-7e851f99feea4dd49f5e1945bf4c8c6e

Reaktionsgleichung

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
CC(C)=CCCC(C)=CCCC(C)=CCc1ccc2nncc3ccccc3c-2c1=O
farnesyl dibenzodiazepinone
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

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeprovided by primary metabolism biosynthetic pathways present in Micromonospora sp
  2. 2
    Sonstige65) that catalyzes a decarboxylative oxidation reaction

Vorschrift

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).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07297524B2uspto-grants-2007_11