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Literature summary for 1.1.99.B12 extracted from

  • Li, R.; Reed, D.W.; Liu, E.; Nowak, J.; Pelcher, L.E.; Page, J.E.; Covello, P.S.
    Functional genomic analysis of alkaloid biosynthesis in Hyoscyamus niger reveals a cytochrome P450 involved in littorine rearrangement (2006), Chem. Biol., 13, 513-520.
    View publication on PubMed
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Cloned(Commentary)

Cloned (Comment) Organism
expression in yeast. CYP80F1 ORF is cloned into the vector pMDC32 and is used to generate Nicotiana tabacum hairy root cultures. Hyoscyamus niger hairy root cultures are generated in which CYP80F1 is overexpressed Hyoscyamus niger

Organism

Organism UniProt Comment Textmining
Hyoscyamus niger Q1A1B0
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Source Tissue

Source Tissue Comment Organism Textmining
root root-specific expression Hyoscyamus niger
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Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(R)-littorine + acceptor expression in yeast confirms that CYP80F1 catalyzes the oxidation of (R)-littorine with rearrangement to form hyoscyamine aldehyde, a putative precursor to hyoscyamine, and without rearrangement to form 3'-hydroxylittorine Hyoscyamus niger 3'-hydroxylittorine + reduced acceptor
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 ?
(R)-littorine + acceptor expression in yeast confirms that CYP80F1 catalyzes the oxidation of (R)-littorine with rearrangement to form hyoscyamine aldehyde, a putative precursor to hyoscyamine, and without rearrangement to form 3'-hydroxylittorine Hyoscyamus niger hyoscyamine aldehyde + reduced acceptor
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 ?
(S)-littorine + acceptor products are (2'S,3'S)-3'-hydroxylittorine, and a minor amount of (2'S,3'R)-3'-hydroxylittorine Hyoscyamus niger (2'S,3'S)-3'-hydroxylittorine + (2'S,3'R)-3'-hydroxylittorine + ?
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 ?

Synonyms

Synonyms Comment Organism
CYP80F1
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 Hyoscyamus niger

Cofactor

Cofactor Comment Organism Structure
additional information production of the corresponding compounds was found to be dependent on NADPH, but not NADH Hyoscyamus niger

General Information

General Information Comment Organism
malfunction silencing CYP80F1 results in reduced hyoscyamine levels and the accumulation of littorine Hyoscyamus niger
physiological function involvement of the enzyme (CYP80F1) in the tropane alkaloid pathway, in the rearrangement of littorine to hyoscyamine Hyoscyamus niger