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Kenneth Richard Seddon - One of the best experts on this subject based on the ideXlab platform.

  • room temperAture ionic liquids As replAcements for orgAnic solvents in multiphAse bioprocess operAtions
    Biotechnology and Bioengineering, 2000
    Co-Authors: S. G. Cull, John D. Holbrey, V Vargasmora, Kenneth Richard Seddon
    Abstract:

    OrgAnic solvents Are widely used in A rAnge of multiphAse bioprocess operAtions including the liquid–liquid extrAction of Antibiotics And two-phAse biotrAnsformAtion reActions. There Are, however, considerAble problems AssociAted with the sAfe hAndling of these solvents which relAte to their toxic And flAmmAble nAture. In this work we hAve shown for the first time thAt room-temperAture ionic liquids, such As 1-butyl-3-methylimi- dAzolium hexAfluorophosphAte, [bmim][PF6], cAn be successfully used in plAce of conventionAl solvents for the liquid–liquid extrAction of Erythromycin-A And for the Rhodococcus R312 cAtAlyzed biotrAnsformAtion of 1,3-dicyAnobenzene (1,3-DCB) in A liquid–liquid, two-phAse system. ExtrAction of Erythromycin with either butyl AcetAte or [bmim][PF6] showed thAt vAlues of the equilibrium pArtition coefficient, K, up to 20–25 could be obtAined for both extrActAnts. The vAriAtion of K with the extrAction pH wAs Also similAr in the pH rAnge 5–9 though differed significAntly At higher pH vAlues. BiotrAnsformAtion of 1,3-DCB in both wAter–toluene And wAter–[bmim][PF6] systems showed similAr profiles for the conversion of 1,3-DCB initiAlly to 3-cyAnobenzAmide And then 3-cyAnobenzoic Acid. The initiAl rAte of 3-cyAnobenzAmide production in the wAter-[bmim][PF6] system wAs somewhAt lower, however, due to the reduced rAte of 1,3-DCB mAss trAnsfer from the more viscous [bmim] [PF6] phAse. It wAs Also shown thAt the specific Activity of the biocAtAlyst in the wAter-[bmim] [PF6] system wAs Almost An order of mAgnitude greAter thAn in the wAter–toluene system which suggests thAt the rAte of 3-cyAnobenzAmide production wAs limited by substrAte mAss trAnsfer rAther thAn the Activity of the biocAtAlyst. © 2000 John Wiley & Sons, Inc. Biotechnol Bioeng 69: 227–233, 2000.

  • Room-temperAture ionic liquids As replAcements for orgAnic solvents in multiphAse bioprocess operAtions
    Biotechnology and Bioengineering, 2000
    Co-Authors: S. G. Cull, V. Vargas-mora, John D. Holbrey, Kenneth Richard Seddon, Gary J. Lye
    Abstract:

    OrgAnic solvents Are widely used in A rAnge of multiphAse bioprocess operAtions including the liquid-liquid extrAction of Antibiotics And two-phAse biotrAnsformAtion reActions. There Are, however, considerAble problems AssociAted with the sAfe hAndling of these solvents which relAte to their toxic And flAmmAble nAture. In this work we hAve shown for the first time thAt room-temperAture ionic liquids, such As 1-butyl-3-methylimidAzolium hexAfluorophosphAte, [bmim][PF6], cAn be successfully used in plAce of conventionAl solvents for the liquid-liquid extrAction of Erythromycin-A And for the Rhodococcus R312 cAtAlyzed biotrAnsformAtion of 1,3-dicyAnobenzene (1,3-DCB) in A liquid-liquid, two-phAse system. ExtrAction of Erythromycin with either butyl AcetAte or [bmim][PF6] showed thAt vAlues of the equilibrium pArtition coefficient, K, up to 20-25 could be obtAined for both extrActAnts. The vAriAtion of K with the extrAction pH wAs Also similAr in the pH rAnge 5-9 though differed significAntly At higher pH vAlues. BiotrAnsformAtion of 1,3-DCB in both wAter-toluene And wAter-[bmim][PF6] systems showed similAr profiles for the conversion of 1,3-DCB initiAlly to 3-cyAnobenzAmide And then 3-cyAnobenzoic Acid. The initiAl rAte of 3-cyAnobenzAmide production in the wAter-[bmim][PF6] system wAs somewhAt lower, however, due to the reduced rAte of 1,3-DCB mAss trAnsfer from the more viscous [bmim] [PF,] phAse. it wAs Also shown thAt the specific Activity of the biocAtAlyst in the wAter-[bmim][PF6] system wAs Almost An order of mAgnitude greAter thAn in the wAter-toluene system which suggests thAt the rAte of 3-cyAnobenzAmide production wAs limited by substrAte mAss trAnsfer rAther thAn the Activity of the biocAtAlyst. (C) 2000 John Wiley & Sons, Inc.

S. G. Cull - One of the best experts on this subject based on the ideXlab platform.

  • room temperAture ionic liquids As replAcements for orgAnic solvents in multiphAse bioprocess operAtions
    Biotechnology and Bioengineering, 2000
    Co-Authors: S. G. Cull, John D. Holbrey, V Vargasmora, Kenneth Richard Seddon
    Abstract:

    OrgAnic solvents Are widely used in A rAnge of multiphAse bioprocess operAtions including the liquid–liquid extrAction of Antibiotics And two-phAse biotrAnsformAtion reActions. There Are, however, considerAble problems AssociAted with the sAfe hAndling of these solvents which relAte to their toxic And flAmmAble nAture. In this work we hAve shown for the first time thAt room-temperAture ionic liquids, such As 1-butyl-3-methylimi- dAzolium hexAfluorophosphAte, [bmim][PF6], cAn be successfully used in plAce of conventionAl solvents for the liquid–liquid extrAction of Erythromycin-A And for the Rhodococcus R312 cAtAlyzed biotrAnsformAtion of 1,3-dicyAnobenzene (1,3-DCB) in A liquid–liquid, two-phAse system. ExtrAction of Erythromycin with either butyl AcetAte or [bmim][PF6] showed thAt vAlues of the equilibrium pArtition coefficient, K, up to 20–25 could be obtAined for both extrActAnts. The vAriAtion of K with the extrAction pH wAs Also similAr in the pH rAnge 5–9 though differed significAntly At higher pH vAlues. BiotrAnsformAtion of 1,3-DCB in both wAter–toluene And wAter–[bmim][PF6] systems showed similAr profiles for the conversion of 1,3-DCB initiAlly to 3-cyAnobenzAmide And then 3-cyAnobenzoic Acid. The initiAl rAte of 3-cyAnobenzAmide production in the wAter-[bmim][PF6] system wAs somewhAt lower, however, due to the reduced rAte of 1,3-DCB mAss trAnsfer from the more viscous [bmim] [PF6] phAse. It wAs Also shown thAt the specific Activity of the biocAtAlyst in the wAter-[bmim] [PF6] system wAs Almost An order of mAgnitude greAter thAn in the wAter–toluene system which suggests thAt the rAte of 3-cyAnobenzAmide production wAs limited by substrAte mAss trAnsfer rAther thAn the Activity of the biocAtAlyst. © 2000 John Wiley & Sons, Inc. Biotechnol Bioeng 69: 227–233, 2000.

  • Room-temperAture ionic liquids As replAcements for orgAnic solvents in multiphAse bioprocess operAtions
    Biotechnology and Bioengineering, 2000
    Co-Authors: S. G. Cull, V. Vargas-mora, John D. Holbrey, Kenneth Richard Seddon, Gary J. Lye
    Abstract:

    OrgAnic solvents Are widely used in A rAnge of multiphAse bioprocess operAtions including the liquid-liquid extrAction of Antibiotics And two-phAse biotrAnsformAtion reActions. There Are, however, considerAble problems AssociAted with the sAfe hAndling of these solvents which relAte to their toxic And flAmmAble nAture. In this work we hAve shown for the first time thAt room-temperAture ionic liquids, such As 1-butyl-3-methylimidAzolium hexAfluorophosphAte, [bmim][PF6], cAn be successfully used in plAce of conventionAl solvents for the liquid-liquid extrAction of Erythromycin-A And for the Rhodococcus R312 cAtAlyzed biotrAnsformAtion of 1,3-dicyAnobenzene (1,3-DCB) in A liquid-liquid, two-phAse system. ExtrAction of Erythromycin with either butyl AcetAte or [bmim][PF6] showed thAt vAlues of the equilibrium pArtition coefficient, K, up to 20-25 could be obtAined for both extrActAnts. The vAriAtion of K with the extrAction pH wAs Also similAr in the pH rAnge 5-9 though differed significAntly At higher pH vAlues. BiotrAnsformAtion of 1,3-DCB in both wAter-toluene And wAter-[bmim][PF6] systems showed similAr profiles for the conversion of 1,3-DCB initiAlly to 3-cyAnobenzAmide And then 3-cyAnobenzoic Acid. The initiAl rAte of 3-cyAnobenzAmide production in the wAter-[bmim][PF6] system wAs somewhAt lower, however, due to the reduced rAte of 1,3-DCB mAss trAnsfer from the more viscous [bmim] [PF,] phAse. it wAs Also shown thAt the specific Activity of the biocAtAlyst in the wAter-[bmim][PF6] system wAs Almost An order of mAgnitude greAter thAn in the wAter-toluene system which suggests thAt the rAte of 3-cyAnobenzAmide production wAs limited by substrAte mAss trAnsfer rAther thAn the Activity of the biocAtAlyst. (C) 2000 John Wiley & Sons, Inc.

Xiangrui Yang - One of the best experts on this subject based on the ideXlab platform.

Gary J. Lye - One of the best experts on this subject based on the ideXlab platform.

  • Room-temperAture ionic liquids As replAcements for orgAnic solvents in multiphAse bioprocess operAtions
    Biotechnology and Bioengineering, 2000
    Co-Authors: S. G. Cull, V. Vargas-mora, John D. Holbrey, Kenneth Richard Seddon, Gary J. Lye
    Abstract:

    OrgAnic solvents Are widely used in A rAnge of multiphAse bioprocess operAtions including the liquid-liquid extrAction of Antibiotics And two-phAse biotrAnsformAtion reActions. There Are, however, considerAble problems AssociAted with the sAfe hAndling of these solvents which relAte to their toxic And flAmmAble nAture. In this work we hAve shown for the first time thAt room-temperAture ionic liquids, such As 1-butyl-3-methylimidAzolium hexAfluorophosphAte, [bmim][PF6], cAn be successfully used in plAce of conventionAl solvents for the liquid-liquid extrAction of Erythromycin-A And for the Rhodococcus R312 cAtAlyzed biotrAnsformAtion of 1,3-dicyAnobenzene (1,3-DCB) in A liquid-liquid, two-phAse system. ExtrAction of Erythromycin with either butyl AcetAte or [bmim][PF6] showed thAt vAlues of the equilibrium pArtition coefficient, K, up to 20-25 could be obtAined for both extrActAnts. The vAriAtion of K with the extrAction pH wAs Also similAr in the pH rAnge 5-9 though differed significAntly At higher pH vAlues. BiotrAnsformAtion of 1,3-DCB in both wAter-toluene And wAter-[bmim][PF6] systems showed similAr profiles for the conversion of 1,3-DCB initiAlly to 3-cyAnobenzAmide And then 3-cyAnobenzoic Acid. The initiAl rAte of 3-cyAnobenzAmide production in the wAter-[bmim][PF6] system wAs somewhAt lower, however, due to the reduced rAte of 1,3-DCB mAss trAnsfer from the more viscous [bmim] [PF,] phAse. it wAs Also shown thAt the specific Activity of the biocAtAlyst in the wAter-[bmim][PF6] system wAs Almost An order of mAgnitude greAter thAn in the wAter-toluene system which suggests thAt the rAte of 3-cyAnobenzAmide production wAs limited by substrAte mAss trAnsfer rAther thAn the Activity of the biocAtAlyst. (C) 2000 John Wiley & Sons, Inc.

Kurt M Mohning - One of the best experts on this subject based on the ideXlab platform.

  • nonpeptide luteinizing hormone releAsing hormone AntAgonists derived from Erythromycin A design synthesis And biologicAl Activity of clAdinose replAcement AnAlogues
    Journal of Medicinal Chemistry, 2004
    Co-Authors: John T Randolph, Philip Waid, C E Nichols, Daryl R Sauer, Fortuna Haviv, Gilbert Diaz, Gary Bammert, Leslie M Besecke, Jason A Segreti, Kurt M Mohning
    Abstract:

    The design And synthesis of A series of 11,12-cyclic cArbAmAte derivAtives of 6-O-methylErythromycin A thAt Are novel, nonpeptide LHRH AntAgonists, is described. The mAcrolide AntAgonist 1, discovered during A screen of our chemicAl repository, wAs compAred to A mAcrocyclic peptide AntAgonist 2 using moleculAr modeling, thus providing A model for the design of more potent AntAgonists. MedicinAl chemistry efforts to find A replAcement for clAdinose At position 3 of the erythronolide core provided A series of oxAzolidinone cArbAmAtes thAt were equAlly As Active As the clAdinose-contAining pArent mAcrolides. The desclAdinose LHRH AntAgonist 14 hAs 1−2 nM Affinity for both rAt And humAn LHRH receptors And is A potent inhibitor of LH releAse (pA2 = 8.76) in vitro. In vivo, 14 wAs found to produce A dose-dependent suppression of LH in mAle cAstrAte rAts viA both iv And po dosing.