Synthesis and evaluation of phosphoramidate amino acid-based inhibitors of sialyltransferases

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Abstract

Several phosphoramidate analogues of CMP-N-acetylneuraminic acid were prepared for evaluation as inhibitors of α-2,3- and α-2,6-sialyltransferase. Central to the synthesis was the oxidative coupling of an amino acid ester with an H-phosphonate to construct the phosphoramidate linkage. All compounds synthesized were weak inhibitors of both of the sialyltransferases as determined by an HPLC-based inhibition assay. © 2002 Elsevier Science Ltd. All rights reserved.

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Whalen, L. J., McEvoy, K. A., & Halcomb, R. L. (2003). Synthesis and evaluation of phosphoramidate amino acid-based inhibitors of sialyltransferases. Bioorganic and Medicinal Chemistry Letters, 13(2), 301–304. https://doi.org/10.1016/S0960-894X(02)00735-7

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