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Literature summary for 1.14.13.216 extracted from

  • Haynes, S.W.; Gao, X.; Tang, Y.; Walsh, C.T.
    Assembly of asperlicin peptidyl alkaloids from anthranilate and tryptophan: a two-enzyme pathway generates heptacyclic scaffold complexity in asperlicin E (2012), J. Am. Chem. Soc., 134, 17444-17447.
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

Cloned (Comment) Organism
gene aspB, recombinant expression in Escherichia coli Aspergillus alliaceus

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
asperlicin C + FADH2 + O2 Aspergillus alliaceus the instability of the product generated from the reaction of AspB with the enantiomer of asperlicin C (ent-asperlicin C) hinders full characterization, formation of an oxidized product, which is stalled prior to intramolecular cyclization en route to an asperlicin E type product asperlicin E + FAD + H2O with NAD(P)H as reducing element, product determination by NMR spectroscopy ?
asperlicin C + FADH2 + O2 Aspergillus alliaceus ATCC 20656 the instability of the product generated from the reaction of AspB with the enantiomer of asperlicin C (ent-asperlicin C) hinders full characterization, formation of an oxidized product, which is stalled prior to intramolecular cyclization en route to an asperlicin E type product asperlicin E + FAD + H2O with NAD(P)H as reducing element, product determination by NMR spectroscopy ?
additional information Aspergillus alliaceus the enzyme converts synthetic asperlicin C or D (and their enantiomers) in the presence of proposed cosubstrate O2 to new products. No activity with asperlicin D and fumiquinazoline F by enzyme AspB ?
-
?
additional information Aspergillus alliaceus ATCC 20656 the enzyme converts synthetic asperlicin C or D (and their enantiomers) in the presence of proposed cosubstrate O2 to new products. No activity with asperlicin D and fumiquinazoline F by enzyme AspB ?
-
?

Organism

Organism UniProt Comment Textmining
Aspergillus alliaceus
-
gene aspB
-
Aspergillus alliaceus ATCC 20656
-
gene aspB
-

Reaction

Reaction Comment Organism Reaction ID
asperlicin C + NAD(P)H + H+ + O2 = asperlicin E + NAD(P)+ + H2O reaction mechanism Aspergillus alliaceus

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
asperlicin C + FADH2 + O2 the instability of the product generated from the reaction of AspB with the enantiomer of asperlicin C (ent-asperlicin C) hinders full characterization, formation of an oxidized product, which is stalled prior to intramolecular cyclization en route to an asperlicin E type product Aspergillus alliaceus asperlicin E + FAD + H2O with NAD(P)H as reducing element, product determination by NMR spectroscopy ?
asperlicin C + FADH2 + O2 with NAD(P)H as reducing element. AspB mediated transformation of asperlicin C to asperlicin E via formation of the transient indole epoxide or a hydroxyiminium adduct (via a FAD-4a-OOH electrophilic oxygen donation to the indole 2, 3-double bond), with presumed alpha stereochemistry Aspergillus alliaceus asperlicin E + FAD + H2O
-
?
asperlicin C + FADH2 + O2 the instability of the product generated from the reaction of AspB with the enantiomer of asperlicin C (ent-asperlicin C) hinders full characterization, formation of an oxidized product, which is stalled prior to intramolecular cyclization en route to an asperlicin E type product Aspergillus alliaceus ATCC 20656 asperlicin E + FAD + H2O with NAD(P)H as reducing element, product determination by NMR spectroscopy ?
asperlicin C + FADH2 + O2 with NAD(P)H as reducing element. AspB mediated transformation of asperlicin C to asperlicin E via formation of the transient indole epoxide or a hydroxyiminium adduct (via a FAD-4a-OOH electrophilic oxygen donation to the indole 2, 3-double bond), with presumed alpha stereochemistry Aspergillus alliaceus ATCC 20656 asperlicin E + FAD + H2O
-
?
additional information the enzyme converts synthetic asperlicin C or D (and their enantiomers) in the presence of proposed cosubstrate O2 to new products. No activity with asperlicin D and fumiquinazoline F by enzyme AspB Aspergillus alliaceus ?
-
?
additional information the enzyme converts synthetic asperlicin C or D (and their enantiomers) in the presence of proposed cosubstrate O2 to new products. No activity with asperlicin D and fumiquinazoline F by enzyme AspB Aspergillus alliaceus ATCC 20656 ?
-
?

Synonyms

Synonyms Comment Organism
aspB
-
Aspergillus alliaceus

Cofactor

Cofactor Comment Organism Structure
FAD FAD binding enzyme Aspergillus alliaceus
NADH
-
Aspergillus alliaceus
NADPH
-
Aspergillus alliaceus

General Information

General Information Comment Organism
evolution AspB, the predicted FAD binding enzyme, is highly homologous to Af12060 from the fumiquinazoline pathway Aspergillus alliaceus