Medical Imaging Convention [rescheduled] Sep 15, 2021 - Sep 16, 2021 — National Exhibition Centre, Birmingham, England
2021 SINAPSE ASM Sep 16, 2021 - Sep 17, 2021 — Technology & Innovation Centre, University of Strathclyde, 99 George Street, Glasgow
Total Body PET 2021 conference [rescheduled] Sep 22, 2021 - Sep 24, 2021 — Virtual Meeting (online)
PET is Wonderful Annual Meeting 2021 Oct 26, 2021 12:00 AM — Virtual Meeting (online)


SINAPSE experts from around Scotland have developed ten online modules designed to explain medical imaging. They are freely available and are intended for non-specialists.

Edinburgh Imaging Academy at the University of Edinburgh offers the following online programmes through a virtual learning environment:

Neuroimaging for Research MSc/Dip/Cert

Imaging MSc/Dip/Cert

PET-MR Principles & Applications Cert

Applied Medical Image Analysis Cert

Online Short Courses

Mechanistic Insights into the Cytochrome P450-Mediated Oxidation and Rearrangement of Littorine in Tropane Alkaloid Biosynthesis

Author(s): P. Nasomjai, D. W. Reed, D. J. Tozer, M. J. G. Peach, A. M. Z. Slawin, P. S. Covello, D. O'Hagan

During the biosynthesis of certain tropane alkaloids, littorine (1) is rearranged to hyoscyamine (3). Recent evidence indicates that this isomerisation is a two-step process in which the first step is an oxidation/rearrangement to give hyoscyamine aldehyde (2). This step is catalysed by CYP80F1, a cytochrome P450 enzyme, which was recently identified from the plant Hyoscyamus niger; CYP80F1 also catalyses the hydroxylation of littorine at the 3'-position. The mechanisms of the reactions catalysed by CYP80F1 were probed with synthetic deutero and arylfluoro analogues of 1. Measurement of the primary kinetic isotope effects indicates that C3' hydrogen abstraction is the rate-limiting step for the oxidation/rearrangement of natural littorine, and for the 3'-hydroxylation reaction of the unnatural S enantiomer of littorine. The character of the intermediates in the oxidation/rearrangement and hydroxylation reaction was probed with the use of arylfluorinated analogues of (R)-littorine (natural stereoisomer) and (S)-littorine (unnatural stereoisomer) as substrates for CYP80F1. The relative conversions of ortho-, meta- and para-fluorolittorine analogues were used to obtain information on the likely intermediacy of either a benzylic radical or benzylic carbocation intermediate. The data suggest that hydroxylation takes place via a benzylic carbocation intermediate, whereas the product profile arising from rearrangement is more consistent with a benzylic radical intermediate.

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ISBN: 1439-4227
Publication Year: 2009
Periodical: Chembiochem
Periodical Number: 14
Volume: 10
Pages: 2382-2393
Author Address: