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Littorine mutase

Definition:

EC Tree > 1 Oxidoreductases > 1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen > 1.14.14 With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor > 1.14.14.195 littorine mutase
Littorine mutase from Hyoscyamus niger and Anisodus acutangulus acts in hyoscyamine (atropine) and scopolamine biosynthesis; it hydroxylates littorine to a 1,2-diol that spontaneously dehydrates with pinacol rearrangement to hyoscyamine aldehyde.

References:

[1]. Li R., et al. Functional genomic analysis of alkaloid biosynthesis in Hyoscyamus niger reveals a cytochrome P450 involved in littorine rearrangement (2006), Chem. Biol. , 13, 513-520.

[2]. Nasomjai P., et al. Mechanistic insights into the cytochrome P450-mediated oxidation and rearrangement of littorine in tropane alkaloid biosynthesis (2009), Chembiochem , 10, 2382-2393.

[3]. Sandala G.M., et al. The carbon-skeleton rearrangement in tropane alkaloid biosynthesis (2008), J. Am. Chem. Soc. , 130, 10684-10690.

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