Journal of Lipid Research, Vol 29, 94-101, Copyright © 1988 by Lipid Research, Inc.
Synthesis of regiospecifically labeled [18O]glycolic acid and [18O]acyldihydroxyacetone phosphate
DM Peterson, RA Martinez, N Satsangi, ST Weintraub, PL Stotter and SJ Friedberg
Department of Medicine, University of Texas Health Science Center, San Antonio.
Methods are detailed for the preparation of [2-18O]glycolate from
chloroacetic acid and for the direct conversion of these intermediates to
regiospecifically labeled [2-18O]-2-O-acylglycolic acids containing
approximately 90% 18O at the C-O-acyl bond. Methods are also detailed for
optimization of reaction conditions and yields for each synthetic step in
previously published methods for the preparation of 1-O-
acyldihydroxyacetone-3-O-phosphate (DHAP) from acyloxyacetic acid (i.e.,
2-O-acylglycolic acid), where acyl is tetradecanoyl, hexadecanoyl, or
heptadecanoyl. The optimized reaction conditions generate 1-O-acyl DHAP in
its acid form, both in high overall yield and in high purity, without
requiring a final chromatographic purification of the product, 1-O-acyl
DHAP. Combining these new methods, efficient and facile preparations of
regiospecifically labeled [1-18O]-1-O- hexadecanoyl DHAP and
[1-18O]-1-O-heptadecanoyl DHAP have now been demonstrated, in which
approximately 90% 18O is specifically located only at the C-O-acyl
position. Some mechanistic postulates are offered to account for the
optimized yields, regioselectivities, and high 18O incorporation which are
observed in the reactions we have employed to generate 1-O-acyl DHAP from
glycolate intermediates.
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