title: Discovery, synthesis, and insecticidal activity of cycloaspeptide E.
abstract: Several Penicillia and one Tricothecium strain produced a new, insecticidally active member of the cycloaspeptide family, with the proposed name cycloaspeptide E (1). The structure, which was determined on the basis of spectroscopic (NMR, UV, MS) data and Marfey amino acid analysis, was the tyrosine desoxy version of cycloaspeptide A (2). Two synthetic routes to compound 1 were developed: one a partial synthesis from 2 and the other a total synthesis from methyl alaninate hydrochloride. Cycloaspeptide E, the first member of this series not to contain a tyrosine moiety, is also the first to be reported with insecticidal activity.
authors.affiliation: Dow AgroSciences, Indianapolis, Indiana 46268, USA. plewer@dow.com
authors.forename: Paul
authors.initials: P
authors.lastname: Lewer
authors.forename: Paul R
authors.initials: PR
authors.lastname: Graupner
authors.forename: Donald R
authors.initials: DR
authors.lastname: Hahn
authors.forename: Laura L
authors.initials: LL
authors.lastname: Karr
authors.forename: Dennis O
authors.initials: DO
authors.lastname: Duebelbeis
authors.forename: Justin M
authors.initials: JM
authors.lastname: Lira
authors.forename: Peter B
authors.initials: PB
authors.lastname: Anzeveno
authors.forename: Stephen C
authors.initials: SC
authors.lastname: Fields
authors.forename: Jeffrey R
authors.initials: JR
authors.lastname: Gilbert
authors.forename: Cedric
authors.initials: C
authors.lastname: Pearce
mesh_terms: D000818:Animals; D001203:Ascomycota / Q000737:chemistry*; D007306:Insecticides / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D007915:Lepidoptera / Q000187:drug effects*; D015394:Molecular Structure; D010407:Penicillium / Q000737:chemistry*; D010456:Peptides, Cyclic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D007306:Insecticides; D010456:Peptides, Cyclic; C515367:cycloaspeptide E