Premium
Chemoenzymatic Synthesis of a Multivalent Aminoglycoside
Author(s) -
Miura Yoshiko,
Ikeda Takayasu,
Wada Natsuko,
Kobayashi Kazukiyo
Publication year - 2003
Publication title -
macromolecular bioscience
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.924
H-Index - 105
eISSN - 1616-5195
pISSN - 1616-5187
DOI - 10.1002/mabi.200300005
Subject(s) - amikacin , chemistry , aminoglycoside , protease , bacillus subtilis , enzyme , organic chemistry , biochemistry , antibiotics , bacteria , biology , genetics
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.