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Nucleic Acids Symposium Series 2003 3(1):33-34; doi:10.1093/nass/3.1.33
© 2003 by Oxford University Press
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First synthesis of L-enantio-uracil dinucleotide

Takanori Miyashita, Shinji Sakata and Hiroyuki Hayakawa

Chemistry & Pharmacology Laboratory, Biochemicals Division, Yamasa Corporation, 10-1, Araoicho 2-Chome Choshi, Chiba-Ken 288-0056, Japan

L-Enantio-uracil dinucleotide, which consists of two L-uridylic acids and one pyrophosphate, was synthesized for the first time in our laboratory. Benzolyated L-uridine was prepared by a steroselective glycosylation of silylated uracil with L-1-acetoxy-2, 3, 5-tri-O-benzoylribose (L-ABR). After deprotection, L-uridine was converted to L-UP4U by the treatment of L-UMP morpholidate with triethyammonium pyrophosphate (TEA-PPi). Spectral data of synthesized L-UP4U are given in a reference. All spectral data were identical with those of the D-enantiomer except the optical rotation. It showed a positive value compared to the D-enantiomer having a negative value.


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