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Synthesis and 15 N‐ and 17 O‐NMR Spectra of 5‐Methyl( 15 N 2 )[ O 2 , O 4 ‐ 17 O 2 ]uridine (= ( 15 N 2 )[ O 2 , O 4 ‐ 17 O 2 ]Ribosylthymine)
Author(s) -
Amantea Antonio,
Walser Markus,
Séquin Urs,
Strazewski Peter
Publication year - 1995
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19950780507
Subject(s) - chemistry , nmr spectra database , nuclear magnetic resonance spectroscopy , hydrolysis , heteronuclear molecule , phosphorus 31 nmr spectroscopy , spectral line , stereochemistry , crystallography , medicinal chemistry , organic chemistry , physics , astronomy
The 5‐methyl( 15 N 2 )[ O 2 , O 4 ‐ 17 O 2 ]uridine (= ( 15 N 2 )[ O 2 , O 4 ‐ 17 O 2 ]ribosylthymine; 15 ) was synthesized and analyzed by 15 N‐ and 17 O‐NMR spectroscopy. ( 15 N 2 )Urea was condensed with 2,3‐dibromo‐2‐methylpropanoyl chloride ( 3 ) and cyclized to form ( 15 N 2 )thymine ( 5 ). After glycosidation, the 17 O isotopes were introduced in two separate steps: hydrolytic ring opening of 2,5′‐anhydro derivative 9 and hydrolysis of 3‐nitro‐1 H ‐1,2,4‐triazole derivative 12 with labelled water in the presence of a strong base. The 15 N‐ and 17 O‐NMR spectra ( Fig. ) of 15 in phosphate‐buffered water serve as references for heteronuclear NMR spectra of labelled RNA fragments.