Mild method for cleavage of dehydroalanine units: highly efficient conversion of nocathiacin I to nocathiacin IV.
Thiazolyl peptide antibacterial nocathiacin I (1) was converted to nocathiacin IV (4) in high yield using iodomethane and hydriodic acid in THF at 45 degrees C. Several simplified dehydroalanine-containing systems undergo dehydroalanine cleavage under the same conditions, although in these cases iodomethane is not needed for efficient conversion. The mild reaction conditions are in contrast with other methods described in the literature.
Regueiro-Ren
Alicia
A
The Bristol-Myers Squibb Pharmaceutical Research Institute, 5 Research Parkway, Wallingford, Connecticut 06492, USA. alicia.regueiroren@bms.com
Ueda
Yasutsugu
Y
D000409:Alanine / Q000031:analogs & derivatives* / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D036341:Intercellular Signaling Peptides and Proteins; D015394:Molecular Structure; D010455:Peptides; D010456:Peptides, Cyclic / Q000138:chemical synthesis*; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry*
D000900:Anti-Bacterial Agents; D036341:Intercellular Signaling Peptides and Proteins; D010455:Peptides; D010456:Peptides, Cyclic; D013844:Thiazoles; C463319:nocathiacin I; C473548:nocathiacin IV; D000409:Alanine