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N-Demethylation of nocathiacin I via photo-oxidation
Authors:Li Wenying  Huang Stella  Liu Xiaohong  Leet John E  Cantone Joseph L  Lam Kin S
Institution:aBristol-Myers Squibb Research and Development, 5 Research Parkway, Wallingford, CT 06492, USA
Abstract:In order to improve aqueous solubility of nocathiacin I (1), a potent antibacterial agent, N-demethylation of the amino-sugar moiety was sought. Irradiation of 1 in DMF/CH2Cl2 with UV light of 380 nm led to a cyclic product 2, which was hydrolyzed to yield the desired nocathiacin VI (3). Treatment of 1 with shorter UV light caused trans–cis isomerization of a c–c double bond.
Keywords:Antibacterial  Nocathiacin  Photo reaction  Oxidation  Demethylation
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