title: Synthesis and antibacterial activity of nocathiacin I analogues.
abstract: Stereoselective reduction of dehydroalanine double bond in nocathiacin I afforded the primary amide 2. Enzymatic hydrolysis of the amide 2 provided the carboxylic acid 3, which upon coupling with a variety of amines furnished amides 4-32. Some of these semi-synthetic derivatives have retained very good antibacterial activity and have improved aqueous solubility.
authors.affiliation: The Bristol-Myers Squibb Pharmaceutical Research Institute, 5 Research Parkway, Wallingford, CT 06492, USA. b.narasimhulunaidu@bms.com
authors.forename: B Narasimhulu
authors.initials: BN
authors.lastname: Naidu
authors.forename: Margaret E
authors.initials: ME
authors.lastname: Sorenson
authors.forename: John D
authors.initials: JD
authors.lastname: Matiskella
authors.forename: Wenying
authors.initials: W
authors.lastname: Li
authors.forename: Justin B
authors.initials: JB
authors.lastname: Sausker
authors.forename: Yunhui
authors.initials: Y
authors.lastname: Zhang
authors.forename: Timothy P
authors.initials: TP
authors.lastname: Connolly
authors.forename: Kin S
authors.initials: KS
authors.lastname: Lam
authors.forename: Joanne J
authors.initials: JJ
authors.lastname: Bronson
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Pucci
authors.forename: Hyekyung
authors.initials: H
authors.lastname: Yang
authors.forename: Yasutsugu
authors.initials: Y
authors.lastname: Ueda
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013293:Enterococcus faecalis / Q000187:drug effects*; D066298:In Vitro Techniques; D036341:Intercellular Signaling Peptides and Proteins; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D012995:Solubility; D013211:Staphylococcus aureus / Q000187:drug effects*; D013237:Stereoisomerism; D013296:Streptococcus pneumoniae / Q000187:drug effects*; D013329:Structure-Activity Relationship; D014867:Water / Q000737:chemistry
chemical_list: D000900:Anti-Bacterial Agents; D036341:Intercellular Signaling Peptides and Proteins; D010455:Peptides; C463319:nocathiacin I; D014867:Water