Synthesis and Characterization of Stereoisomers of 5,6-Dihydro-5,6-Dihydroxythymidine

Y. Vaishnav Radiation Biochemistry Department, Armed Forces Radiobiology Research Institute, Bethesda, MD, 20889-5145

E. Holwitt Radiation Biochemistry Department, Armed Forces Radiobiology Research Institute, Bethesda, MD, 20889-5145

C. Swenberg Radiation Biochemistry Department, Armed Forces Radiobiology Research Institute, Bethesda, MD, 20889-5145

H.-C. Lee Department of Biochemistry, School of Hygiene and Public Health The Johns Hopkins University, 615 North Wolfe Street, Baltimore, MD, 21205

L.-S. Kan Department of Biochemistry, School of Hygiene and Public Health The Johns Hopkins University, 615 North Wolfe Street, Baltimore, MD, 21205

Abstract

Six products were isolated by reverse phase HPLC from the reaction of thymidine with osmium tetroxide. Four of the products were identified as stereoisomers of 5,6-dihydro-5.6-dihydroxythymidine (TG). The absolute configurations of these four compounds (from the shortest to the longest HPLC retention times) were determined by two-dimensional nuclear magnetic resonance spectroscopy to be (-)-trans-5S.6S-, (+)-trans-5R,6R-, (-)-cis-5R,6S-, and (+)-cis-5S,6R-5,6-dihydro-5,6-dihydroxythymidine. The other two products were dimers with unknown linking sites. Parameters of the mass and nuclear magnetic resonance spectra are reported and discussed.

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Synthesis and Characterization of Stereoisomers of 5,6-Dihydro-5,6-Dihydroxythymidine

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Synthesis and Characterization of Stereoisomers of 5,6-Dihydro-5,6-Dihydroxythymidine

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