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Communication | Regular issue | Vol 63, No. 4, 2004, pp.779-784
Published online, 20th February, 2004
DOI: 10.3987/COM-04-10009
Synthesis of CMP-sialic Acid Mimics That Have 5-Fluorouracil for Cytosine and the C-Terminal's Peptide Bond for the Phosphate Group: Targeting Inhibitors of Sialyltransferases

Shinji Nakahara, Toru Tanaka, Kazuharu Noguchi, Kenji Nozaki, Shuichi Tsuji, Tsuyoshi Miura, and Tetsuya Kajimoto*

*Department of Biotechnology, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei-shi, Tokyo 184-8588, Japan


Novel mimics of cytidine 5'-monophosphate-sialic acid (CMP-sialic acid) were designed and synthesized for targeting inhibitors of sialyltransferases on the basis of the phenomenon that the tautomerization of 5-fluorouracil from the lactam to the lactim form produces a structure similar to that of cytosine, and the C-terminal's peptide bond can be a bioisoster of a phosphate group. Since γ-N1-(5-fluorouracilyl)-β-hydroxy-α-L-amino acid, a key synthetic intermediate, was easily prepared using the enzyme-catalyzed aldol reaction, the synthesis of the mimics of the CMP-sialic acid was attained in a short step.