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Synthesis of [ 15 N] and [side‐chain 1‐ 13 C] isotopomers of 1‐(2‐nitrophenyl)ethyl phosphates
Author(s) -
Corrie John E. T.
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<403::aid-jlcr856>3.0.co;2-6
Subject(s) - chemistry , nitration , isotopomers , trifluoroacetic anhydride , phosphate , side chain , ethanol , organic chemistry , saponification , mass spectrometry , medicinal chemistry , chromatography , molecule , polymer
Nitration of 1‐phenylethyl acetate with NH 4 NO 3 ‐trifluoroacetic anhydride gave a mixture of ortho‐ and para ‐nitro products, which were separable by chromatography after saponification of the acetate. The ortho ‐isomer [1‐(2‐nitrophenyl)ethanol] was converted to the 1‐(2‐nitrophenyl)ethyl esters of monomethyl phosphate and of the γ‐phosphate of ATP. The title isotopomers were prepared using either ammonium [ 15 N]nitrate or [side‐chain 1‐ 13 C]1‐phenylethyl acetate as starting materials. A correction is made to the reported 1 H NMR spectrum of caged ATP and the effects of isotopic substitution on the mass spectral fragmentation of 1‐(2‐nitrophenyl)ethanol are tabulated.