Synthesis of regiospecifically labeled [18O]glycolic acid and [18O]acyldihydroxyacetone phosphate.

D. M. Peterson, R. A. Martinez, N. Satsangi, Susan E Weintraub, P. L. Stotter, S. J. Friedberg

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Abstract

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.

Original languageEnglish (US)
Pages (from-to)94-101
Number of pages8
JournalJournal of Lipid Research
Volume29
Issue number1
StatePublished - Jan 1988

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glycolic acid
Phosphates
Acids
Regioselectivity
Purification

ASJC Scopus subject areas

  • Endocrinology

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Peterson, D. M., Martinez, R. A., Satsangi, N., Weintraub, S. E., Stotter, P. L., & Friedberg, S. J. (1988). Synthesis of regiospecifically labeled [18O]glycolic acid and [18O]acyldihydroxyacetone phosphate. Journal of Lipid Research, 29(1), 94-101.

Synthesis of regiospecifically labeled [18O]glycolic acid and [18O]acyldihydroxyacetone phosphate. / Peterson, D. M.; Martinez, R. A.; Satsangi, N.; Weintraub, Susan E; Stotter, P. L.; Friedberg, S. J.

In: Journal of Lipid Research, Vol. 29, No. 1, 01.1988, p. 94-101.

Research output: Contribution to journalArticle

Peterson, DM, Martinez, RA, Satsangi, N, Weintraub, SE, Stotter, PL & Friedberg, SJ 1988, 'Synthesis of regiospecifically labeled [18O]glycolic acid and [18O]acyldihydroxyacetone phosphate.', Journal of Lipid Research, vol. 29, no. 1, pp. 94-101.
Peterson, D. M. ; Martinez, R. A. ; Satsangi, N. ; Weintraub, Susan E ; Stotter, P. L. ; Friedberg, S. J. / Synthesis of regiospecifically labeled [18O]glycolic acid and [18O]acyldihydroxyacetone phosphate. In: Journal of Lipid Research. 1988 ; Vol. 29, No. 1. pp. 94-101.
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