N-Demethylation of nocathiacin I via photo-oxidation.
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/CH(2)Cl(2) 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.
Li
Wenying
W
Bristol-Myers Squibb Research and Development, 5 Research Parkway, Wallingford, CT 06492, USA. wenying.li@bms.com
Huang
Stella
S
Liu
Xiaohong
X
Leet
John E
JE
Cantone
Joseph L
JL
Lam
Kin S
KS
D000890:Anti-Infective Agents / Q000494:pharmacology; D002626:Chemistry, Pharmaceutical / Q000379:methods; D015195:Drug Design; D006868:Hydrolysis; D036341:Intercellular Signaling Peptides and Proteins; D008027:Light; D008745:Methylation; D008956:Models, Chemical; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010100:Oxygen / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry*; D012995:Solubility; D012997:Solvents / Q000737:chemistry; D013329:Structure-Activity Relationship; D014466:Ultraviolet Rays
D000890:Anti-Infective Agents; D036341:Intercellular Signaling Peptides and Proteins; D010455:Peptides; D012997:Solvents; C463319:nocathiacin I; D010100:Oxygen