Organic & biomolecular chemistry

Synthesis of 1-β-O-acyl glucuronides of diclofenac, mefenamic acid and (S)-naproxen by the chemo-selective enzymatic removal of protecting groups from the …

A Baba, T Yoshioka

Index: Baba, Akiko; Yoshioka, Tadao Organic and Biomolecular Chemistry, 2006 , vol. 4, # 17 p. 3303 - 3310

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Citation Number: 26

Abstract

Using a straightforward chemo-enzymatic procedure, 1-β-O-acyl glucuronides of three non- steroidal anti-inflammatory drugs, diclofenac (DF) 5, mefenamic acid (MF) 6 and (S)- naproxen (NP) 7, were prepared. Caesium salts of these carboxylic acid drugs reacted with commercially available methyl 2, 3, 4-tri-O-acetyl-1-bromo-1-deoxy-α-D-glucopyranuronate 4 to give exclusively the corresponding 1-β-O-acyl glucuronides 8–10 in moderate yields. ...