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Synthesis of a tritium labelled phospholipase A 2 inhibitor: A ligand for macromolecular 3 H NMR spectroscopy
Author(s) -
Culf A. S.,
Morimoto H.,
Williams P. G.,
Lockley W. J. S.,
Primrose W. U.,
Jones J. R.
Publication year - 1996
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/(sici)1099-1344(199604)38:4<373::aid-jlcr844>3.0.co;2-u
Subject(s) - chemistry , tritium , nuclear magnetic resonance spectroscopy , ligand (biochemistry) , amide , tritium illumination , alkene , acylation , stereochemistry , organic chemistry , catalysis , biochemistry , physics , receptor , nuclear physics
A tritium labelled phospholipase A 2 (PLA 2 ) amide analogue inhibitor was prepared by the reduction of an alkene precursor. Diimide, heterogeneous and homogeneous metal catalyzed reduction methods were assessed for their suitability for the preparation of a tritiated ligand for 3 H NMR spectroscopic studies. The chosen homogeneous metal‐catalyzed method gave a product of specific activity 57 Ci mmol −1 , which was isolated by flash chromatography. The binding of this tritiated substrate to bovine pancreatic PLA 2 was observed by 3 H NMR spectroscopy in the presence of calcium ions. Chemical shift changes suggest that the tritium atoms are located within the hydrophobic pocket of the protein, close to two phenylalanine residues.