Microbial hydroxylation of imidacloprid for the synthesis of highly insecticidal olefin

    imidacloprid

    论文转载

    Microbialhydroxylationofimidaclopridforthesynthesisofhighly

    insecticidalolefinimidacloprid

    Dai,YJ.;Yuan,S.;Ge,FI;Chen,T.;Xu,S.C.;Ni,J.P

    NanjingNormalUniv,JiangsuKeyLabBioresourceTechnol,KeyLabMicrobialTechnol,CoilLifeSci,Nanjing2l0097,PeoplesRChina.

    JiangsuPesticideReslnst,Nanjing2l0036,PeoplesRChina.

    Yuan,S,NanjingNormalUniv,JiangsuKeyLabBioresourceTechnol,KeyLabMicrobialTechnol,CoilLifeSci,Nanjing210097,

    PeoplesRChina.shengyuan@email.njnu.edu.cn

    Abstract:Microorganismsthatbringabouttheaerobictransformationofimidacloprid(IMI1wereisolatedand

    screened,andthemicrobialregio.andstereoselectivehydroxylationofIM1wasstudied.Somebacteriaandfungi

    trans~rmedIMIto5-hydroxylIMI.BacteriumStenotrophomonasmaltophiliaCGMCC1.1788restingcellstrans.

    formedIMIintoR-5-hydroxylIMIatthehighestconversionrate.Theenzymecatalyzedthestereoselectivehy.

    droxylationatpositionC12ofIMIintheimidazolidinering.Underacidicconditions.5.hydroxylIM1wasconverted

    intoolefinIMIinhighmolarconversionyield.TheolefinIMIexhibitedabout19and2.2timesmoreinsecticidal

    efficacythanIMIagainsthorsebeanaphidimagoandnymph,respectively,andabout1.4time

smoreactivethanIMI

    againstbrownplanthopperimago.111etransformationrateOfIMIbyrestingcellsofS.maltophiliaCGMCC1.1788

    waspromotedsignificantlybysomecarbohydratesandorganicacids.Thereactionmediumwith5%sucrose

    resultedin8_3timesgreaterbiotransformationyieldascomparedwiththatwithoutsucrose. Keywords:APIS-MEILIFERA;RESTrNGCELLS;METABOLITES;IDENTIFICATION;EFFICACY:CR0PS;

    PLANT:ACID

    AppliedMicrobiologyandBiotechnology2006,71(6):927—934

    Chemoenzymaticsynthesisofenantiopuregeminallydimethylated

    cyclopropane--basedC?-2--andpseudo--C--2--symmetricdiamines

    Feng,G.Q.;Wang,D.X.;Zheng,Q.;Wang,M.X.

    ChineseAcadSci,InstChem,BiolChemLab,BeijingNatlLabMolSci,Beijing100080,PeoplesRChina.

    Wang,MX,ChineseAcadSci,lnstChem,BiolChemLab,BeijingNatlLabMolSci,Beijingl00080,PeoplesRChina.

    mxwang@iccas.ac.cn

    Abstract:Enantiopure(-)-(is,3S)-2,2-dimethyl一3-(2一

    methylprop-1-eny1)cyclopropanecarboxamide2and(+).(IR,

    3R)-2,2-dimethyl一3(2-methylprop一

    1-eny1)cyclopropanecarboxylicacid3wereeasilyobtainedfromanmltigramscale biotransformationofracemicalnideornitrileinthepresenceofRhodococcuserythropolisAJ270wholecellcatalyst

    underverymildconditions.Coupledwithefficientandconvenientchemicalmanipulations,comprisingmainlyofthe

    Curtiusrearrangement,oxidation,andreductionreactions,chiralC.2.symmetric(1S,2S).3,3.dimethylcyclopropane.

    1,2一diamine6and((1R,3R)一

    3-(aminomethy1)-2,2-dimethylcyclopropy1)methanamine8andpseudo.C.2.symmetric