Chemoenzymatic Synthesis of a Multivalent Aminoglycoside

Yoshiko Miura; Takayasu Ikeda; Natsuko Wada; Kazukiyo Kobayashi

doi:10.1002/mabi.200300005

Chemoenzymatic Synthesis of a Multivalent Aminoglycoside

Yoshiko Miura, Takayasu Ikeda, Natsuko Wada, Kazukiyo Kobayashi

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

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.

Original language	English
Pages (from-to)	662-667
Number of pages	6
Journal	Macromolecular Bioscience
Volume	3
Issue number	11
DOIs	https://doi.org/10.1002/mabi.200300005
Publication status	Published - Nov 24 2003
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biotechnology
Bioengineering
Biomaterials
Polymers and Plastics
Materials Chemistry

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10.1002/mabi.200300005

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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.",

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T1 - Chemoenzymatic Synthesis of a Multivalent Aminoglycoside

AU - Miura, Yoshiko

AU - Ikeda, Takayasu

AU - Wada, Natsuko

AU - Kobayashi, Kazukiyo

PY - 2003/11/24

Y1 - 2003/11/24

N2 - 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.

AB - 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.

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DO - 10.1002/mabi.200300005

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ER -

Chemoenzymatic Synthesis of a Multivalent Aminoglycoside

Abstract

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