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J. Biol. Chem., Vol. 264, Issue 23, 13440-13447, 08, 1989
JL Johnson, MM Wuebbens and KV Rajagopalan
An oxidized pterin species, termed compound Z, has been isolated from
molybdenum cofactor-deficient mutants of Escherichia coli and shown to be
the direct product of oxidation of a molybdopterin precursor which
accumulates in these mutants. The complete structural characterization of
compound Z has been accomplished. A carbonyl function at C-1' of the
6-alkyl side chain can be reacted with 2,4-dinitrophenylhydrazine to yield
a phenylhydrazone and can be reduced with borohydride, producing a mixture
of two enantiomers, each with a hydroxyl group on C-1'. Compound Z contains
one phosphate/pterin and no sulfur. The phosphate group is insensitive to
alkaline phosphatase and to a number of phosphodiesterases but is
quantitatively released as inorganic phosphate by mild acid hydrolysis.
From 31P and 1H NMR of compound Z it was inferred that the phosphate is
bound to C-2' and C-4' of a 4-carbon side chain, forming a 6-membered
cyclic structure. Mass spectral analysis showed an MH+ ion with an exact
mass of 344.0401 corresponding to the molecular formula C10H11N5O7P,
confirming the proposed structure.
The structure of a molybdopterin precursor. Characterization of a stable, oxidized derivative
Department of Biochemistry, Duke University Medical Center, Durham, North Carolina 27710.
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