Synthesis and biological activity of a destruxin analogue: D-Lac-6 destruxin E.
A general strategy for the synthesis of destruxin analogues is described and applied to a particular example, D-Lac-6 destruxin E. The tetrapeptide Boc-Ile-N-MeVal-N-MeAla-beta-Ala-OMe (2) was chosen as the basic starting compound, and its preparation was optimized. This fragment was then coupled with the compound (D)Lac-Pro, and the resulting peptide was cyclized by the DEPC or DPPA/HOBt/DMAP methods at 21 and 30% yield, respectively. The biological activity of the analogue obtained was established by injection to an insect host.
Calmes
M
M
URA CNRS 0468: Amino acids and Peptides; Synthesis, Methodologies and Applications, University of Montpellier II, France.
Cavelier-Frontin
F
F
Jacquier
R
R
Mercadier
J L
JL
Sabil
S
S
Verducci
J
J
Quiot
J M
JM
Vey
A
A
D000595:Amino Acid Sequence; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D047630:Depsipeptides; D007300:Insect Control; D007814:Larva; D007915:Lepidoptera / Q000187:drug effects; D008969:Molecular Sequence Data; D010456:Peptides, Cyclic / Q000138:chemical synthesis / Q000494:pharmacology*
D000970:Antineoplastic Agents; D047630:Depsipeptides; D010456:Peptides, Cyclic; C082553:lac-6-destruxin E