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Chemoenzymatic Synthesis of a Multivalent Aminoglycoside

✍ Scribed by Yoshiko Miura; Takayasu Ikeda; Natsuko Wada; Kazukiyo Kobayashi

Book ID
102474308
Publisher
John Wiley and Sons
Year
2003
Tongue
English
Weight
110 KB
Volume
3
Category
Article
ISSN
1616-5187

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✦ Synopsis

Abstract

A polymeric aminoglycoside was prepared by a facile chemoenzymatic reaction. Boc‐protected aminoglycoside, amikacin, was chemoselectively esterified with divinyl sebacate at a hydroxyl group in the C6″ position by protease from Bacillus subtilis. The resulting 3,6′,3″,4‴‐tetra‐N‐Boc‐6″‐O‐vinyl sebacate was copolymerized with maltitol 6‐vinyl sebacate to yield a polymeric amikacin. The polymeric amikacin showed a modest inhibitory effect on in vitro protein synthesis, and a little antibiotic activity in minimum inhibitory concentration (MIC) assay in the presence of protease.

The synthesis of Boc‐protected amikacin ester by an enzyme‐catalyzed (protease) esterification.

magnified imageThe synthesis of Boc‐protected amikacin ester by an enzyme‐catalyzed (protease) esterification.

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