Discovery, synthesis, and insecticidal activity of cycloaspeptide E.
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.
Lewer
Paul
P
Dow AgroSciences, Indianapolis, Indiana 46268, USA. plewer@dow.com
Graupner
Paul R
PR
Hahn
Donald R
DR
Karr
Laura L
LL
Duebelbeis
Dennis O
DO
Lira
Justin M
JM
Anzeveno
Peter B
PB
Fields
Stephen C
SC
Gilbert
Jeffrey R
JR
Pearce
Cedric
C
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
D007306:Insecticides; D010456:Peptides, Cyclic; C515367:cycloaspeptide E