Entry Name littorine mutase;
Class Oxidoreductases;BRITE hierarchy
Sysname littorine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (hyoscyamine aldehyde forming)
Reaction(IUBMB) littorine + [reduced NADPH---hemoprotein reductase] + O2 = hyoscyamine aldehyde + [oxidized NADPH---hemoprotein reductase] + 2 H2O (overall reaction) [RN:
R12954 ];
(1a) littorine + [reduced NADPH---hemoprotein reductase] + O2 + 3-hydroxylittorine + [oxidized NADPH---hemoprotein reductase] + H2O [RN:
R13503 ];
(1b) 3-hydroxylittorine = hyoscamine aldehyde + H2O (spontaneous) [RN:
R13504 ]
Reaction(KEGG) Substrate littorine [CPD:
C10860 ];
[reduced NADPH---hemoprotein reductase] [CPD:
C03024 ];
O2 [CPD:
C00007 ];
3-hydroxylittorine [CPD:
C23043 ]
Product hyoscyamine aldehyde [CPD:
C22466 ];
[oxidized NADPH---hemoprotein reductase] [CPD:
C03161 ];
H2O [CPD:
C00001 ];
hyoscamine aldehyde
Comment Isolated from the plants Hyoscyamus niger (black henbane) and Anisodus acutangulus. Involved in the biosynthesis of the alkaloids hyoscyamine (atropine) and scopalamine. The reaction involves hydroxylation of littorine, giving a 1,2-diol that undergoes a spontaneous dehydration accompanied by pinacol rearrangement.
History EC 1.14.14.195 created 2025
Pathway ec00960 Tropane, piperidine and pyridine alkaloid biosynthesis
Orthology Reference Authors Li R, Reed DW, Liu E, Nowak J, Pelcher LE, Page JE, Covello PS.
Title Functional genomic analysis of alkaloid biosynthesis in Hyoscyamus niger reveals a cytochrome P450 involved in littorine rearrangement.
Journal Sequence Reference Authors Sandala GM, Smith DM, Radom L.
Title The carbon-skeleton rearrangement in tropane alkaloid biosynthesis.
Journal Reference Authors Nasomjai P, Reed DW, Tozer DJ, Peach MJ, Slawin AM, Covello PS, O'Hagan D.
Title Mechanistic insights into the cytochrome P450-mediated oxidation and rearrangement of littorine in tropane alkaloid biosynthesis.
Journal Reference Authors Cui L, Huang F, Zhang D, Lin Y, Liao P, Zong J, Kai G.
Title Transcriptome exploration for further understanding of the tropane alkaloids biosynthesis in Anisodus acutangulus.
Journal Other DBs
