Isotopically labelled tropane alkaloids. The synthesis of (RS)-[3',3'-2H2]- and (RS)-[1'-13C, 3', 3'-2H2]-hyoscyamines for metabolism studies in plants.

Stephen Patterson; David O'Hagan

doi:10.1002/jlcr.543

Isotopically labelled tropane alkaloids. The synthesis of (RS)-[3',3'-²H₂]- and (RS)-[1'-¹³C, 3', 3'-²H₂]-hyoscyamines for metabolism studies in plants.

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Abstract

A synthetic route to isotopically labelled forms of the tropane alkaloid hyoscyamine, including (RS)-[3',3',-H-2(2)]- (2a) and (RS)-[1'-C-13,3',3',-H-2(2)]- (2b) hyoscyamines, involving the reaction between phenylacetyl tropine and formaldehyde is described. The isotopically labelled products enable the metabolism of hyoscyamine to be studied in plants such as Datura stramonium. Copyright (C) 2002 John Wiley Sons, Ltd.

Original language	English
Pages (from-to)	191-198
Number of pages	8
Journal	Journal of Labelled Compounds and Radiopharmaceuticals
Volume	45
DOIs	https://doi.org/10.1002/jlcr.543
Publication status	Published - 15 Mar 2002

Keywords

tropane alkaloids
tropic acid
hyoscyamine
Datura stramonium
biosynthesis
TROPIC ACID
DATURA-STRAMONIUM
STEREOCHEMICAL COURSE
BIOSYNTHESIS
REARRANGEMENT
HYOSCYAMINE
PHENYLLACTATE
PHENYLALANINE
LITTORINE

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title = "Isotopically labelled tropane alkaloids. The synthesis of (RS)-[3',3'-2H2]- and (RS)-[1'-13C, 3', 3'-2H2]-hyoscyamines for metabolism studies in plants.",

abstract = "A synthetic route to isotopically labelled forms of the tropane alkaloid hyoscyamine, including (RS)-[3',3',-H-2(2)]- (2a) and (RS)-[1'-C-13,3',3',-H-2(2)]- (2b) hyoscyamines, involving the reaction between phenylacetyl tropine and formaldehyde is described. The isotopically labelled products enable the metabolism of hyoscyamine to be studied in plants such as Datura stramonium. Copyright (C) 2002 John Wiley Sons, Ltd.",

keywords = "tropane alkaloids, tropic acid, hyoscyamine, Datura stramonium, biosynthesis, TROPIC ACID, DATURA-STRAMONIUM, STEREOCHEMICAL COURSE, BIOSYNTHESIS, REARRANGEMENT, HYOSCYAMINE, PHENYLLACTATE, PHENYLALANINE, LITTORINE",

author = "Stephen Patterson and David O'Hagan",

year = "2002",

month = mar,

day = "15",

doi = "10.1002/jlcr.543",

language = "English",

volume = "45",

pages = "191--198",

journal = "Journal of Labelled Compounds and Radiopharmaceuticals",

issn = "0362-4803",

publisher = "John Wiley \& Sons, Ltd",

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AU - Patterson, Stephen

AU - O'Hagan, David

PY - 2002/3/15

Y1 - 2002/3/15

N2 - A synthetic route to isotopically labelled forms of the tropane alkaloid hyoscyamine, including (RS)-[3',3',-H-2(2)]- (2a) and (RS)-[1'-C-13,3',3',-H-2(2)]- (2b) hyoscyamines, involving the reaction between phenylacetyl tropine and formaldehyde is described. The isotopically labelled products enable the metabolism of hyoscyamine to be studied in plants such as Datura stramonium. Copyright (C) 2002 John Wiley Sons, Ltd.

AB - A synthetic route to isotopically labelled forms of the tropane alkaloid hyoscyamine, including (RS)-[3',3',-H-2(2)]- (2a) and (RS)-[1'-C-13,3',3',-H-2(2)]- (2b) hyoscyamines, involving the reaction between phenylacetyl tropine and formaldehyde is described. The isotopically labelled products enable the metabolism of hyoscyamine to be studied in plants such as Datura stramonium. Copyright (C) 2002 John Wiley Sons, Ltd.

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KW - tropic acid

KW - hyoscyamine

KW - Datura stramonium

KW - biosynthesis

KW - TROPIC ACID

KW - DATURA-STRAMONIUM

KW - STEREOCHEMICAL COURSE

KW - BIOSYNTHESIS

KW - REARRANGEMENT

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KW - PHENYLLACTATE

KW - PHENYLALANINE

KW - LITTORINE

UR - https://www.scopus.com/pages/publications/0037088168

U2 - 10.1002/jlcr.543

DO - 10.1002/jlcr.543

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SN - 0362-4803

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JO - Journal of Labelled Compounds and Radiopharmaceuticals

JF - Journal of Labelled Compounds and Radiopharmaceuticals

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