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. Author manuscript; available in PMC: 2012 Sep 1.
Published in final edited form as: Bioorg Med Chem Lett. 2011 May 6;21(17):5006–5010. doi: 10.1016/j.bmcl.2011.04.128

Scheme 1. Metabolism of protected ManNAc analogs to sialosides.

Scheme 1

(a) BJAB K20 and CHO Lec3 cells lack UDP-GlcNAc 2-epimerase activity, rendering them unable to biosynthesize ManNAc. When these cells are cultured in serum free conditions, they fail to produce sialosides. The UDP-GlcNAc 2-epimerase-deficient cells maintain the ability to transform ManNAc to sialosides and can also metabolize exogenously supplied ManNAc analogs to their sialoside counterparts. (b) N-acyl-modified ManNAc analogs were prepared and added to the media of cultured cells. All analogs were peracetylated to facilitate their entry into cells. All acetyl groups, including the one on the N-glycolyl side chain of Ac5ManNGc, are believed to be removed by intracellular esterases.