Premium
Synthetic approach for unsaturated precursors for parahydrogen induced polarization of choline and its analogs
Author(s) -
Shchepin Roman V.,
Chekmenev Eduard Y.
Publication year - 2013
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.3082
Subject(s) - chemistry , spin isomers of hydrogen , moiety , choline , deuterium , betaine , alkene , aldehyde , combinatorial chemistry , stereochemistry , organic chemistry , hydrogen , biochemistry , physics , quantum mechanics , catalysis
Reported here are (i) a new synthetic approach for preparation of (ii) a new compound class, of –OH, for example, an –OH group is replaced with acetyl protecting group, protected 1,2‐dehydrocholine analogs and (iii) a new synthetic route for betaine aldehyde. The CC bond of 1,2‐dehydrocholine moiety can be used for molecular addition of parahydrogen producing –OH protected hyperpolarized choline by parahydrogen‐induced polarization (PHIP). The reported synthetic approach allows for incorporation of 15 N and deuterium labels, which are necessary for preparation of highly polarized PHIP contrast agents. Isotope labeling with 15 N and/or deuterium was conducted. Hyperpolarized 15 N‐choline enabled by the reported synthetic approach can be potentially used as an imaging biomarker of cancer similar to choline positron emission tomography tracers.