Synthesis and biological evaluation of 5′-glycyl derivatives of uridine as inhibitors of 1,4-β-galactosyltransferase

• New 5′-O-glycyl and 5′-N-glycyl derivatives of uridine were synthesized.
• Compound A4 showed moderate inhibition against 1,4-β-galactosyltransferase.
• STD NMR study confirmed binding of compound A4 into bovine serum albumin.

New 5′-glycyl derivatives of uridine containing fragments of varying lipophilicity were synthesized as analogues of natural peptidyl antibiotics. One of the studied compounds, 5′-O-(N-succinylglycyl)-2′,3′-O-isopropylideneuridine (A4), showed moderate inhibition against 1,4-β-galactosyltransferase. However, additional studies showed that the observed inhibitory effect was due to binding to bovine serum albumin, which was used in assays as a stabilizer.

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