Creating Pyrethrin Mimetic Phosphonates as Chemical Genetics Tools Targeting the GDSL Esterase/Lipase TcGLIP to Investigate Pyrethrin Biosynthesis.

ABSTRACT: Pyrethrins from Tanacetum cinerariifolium are natural pesticides that exhibit high knockdown and killing activities against flying insects such as disease-spreading mosquitoes. Despite the increasing demand for pyrethrins, the mechanism of pyrethrin biosynthesis remains elusive. To elucidate it, we for the first time created pyrethrin mimetic phosphonates targeting the GDSL esterase/lipase (GELP or TcGLIP) underpinning pyrethrin biosynthesis. The compounds were synthesized by reacting mono-alkyl or mono-benzyl-substituted phosphonic dichloride with pyrethrolone, the alcohol moiety of pyrethrin I and II, and then p-nitrophenol. n-Pentyl (C5) and n-octyl (C8)-substituted compounds were the most potent of the (S)_p,(S)_c, and (R

SUBMITTER: Matsuo N 

PROVIDER: S-EPMC10291546 | biostudies-literature | 2023 Jun

REPOSITORIES: biostudies-literature