公开(公告)号：US11779911B2

公开(公告)日：2023-10-10

申请号：US17390136

申请日：2021-07-30

申请人： Provivi, Inc.

发明人： Keith M. Wampler ,  Peter Meinhold ,  Pedro Coelho ,  Vu Bui ,  Hasan Mehdi

IPC分类号： B01J31/22 ,  C07C29/147 ,  C07C67/08 ,  C07C67/343 ,  C07C45/41 ,  C07C6/04 ,  C07C67/293

CPC分类号： B01J31/2278 ,  C07C6/04 ,  C07C29/147 ,  C07C45/41 ,  C07C67/08 ,  C07C67/293 ,  C07C67/343 ,  B01J2231/543 ,  B01J2531/64 ,  B01J2531/66 ,  C07B2200/09 ,  C07C2531/22 ,  C07C67/343 ,  C07C69/533 ,  C07C29/147 ,  C07C33/025 ,  C07C67/08 ,  C07C69/145 ,  C07C45/41 ,  C07C47/21 ,  C07C6/04 ,  C07C11/21 ,  C07C67/293 ,  C07C69/145

摘要： In one aspect, the invention provides a method for synthesizing a fatty olefin derivative. The method includes: a) contacting an olefin according to Formula I




with a metathesis reaction partner according to Formula IIb





in the presence of a metathesis catalyst under conditions sufficient to form a metathesis product according to Formula IIIb:





and

b) converting the metathesis product to the fatty olefin derivative. Each R1 is independently selected from H, C1-18 alkyl, and C2-18 alkenyl; R2b is C1-8 alkyl; subscript y is an integer ranging from 0 to 17; and subscript z is an integer ranging from 0 to 17. In certain embodiments, the metathesis catalyst is a tungsten catalyst or a molybdenum catalyst. In various embodiments, the fatty olefin derivative is a pheromone. Pheromone compositions and methods of using them are also described.

公开(公告)号：US20230095259A1

公开(公告)日：2023-03-30

申请号：US17988238

申请日：2022-11-16

申请人： Provivi, Inc.

发明人： Keith M. Wampler ,  Richard L. Pederson

IPC分类号： C07C67/475 ,  C07F15/00 ,  C07C29/157 ,  B01J31/22 ,  B01J31/18 ,  B01J31/02

摘要： Disclosed herein are methods for synthesizing fatty olefin metathesis products of high Z-isomeric purity from olefin feedstocks of low Z-isomeric purity. The methods include contacting a contacting an olefin metathesis reaction partner, such as acylated alkenol or an alkenal acetal, with an internal olefin in the presence of a Z-selective metathesis catalyst to form the fatty olefin metathesis product. In various embodiments, the fatty olefin metathesis products are insect pheromones. Pheromone compositions and methods of using them are also described.

公开(公告)号：US20220177857A1

公开(公告)日：2022-06-09

申请号：US17550212

申请日：2021-12-14

申请人： Provivi, Inc.

发明人： Effendi LEONARD ,  Micah SHEPPARD ,  Thomas HEEL ,  Kathryn Christina WU

IPC分类号： C12N9/04 ,  C12N9/02 ,  C12N9/18 ,  C12N15/52 ,  C12N15/81

摘要： The present application relates to methods to improve biomass or lipid production in a microorganism from one or more fatty acid and one or more simple carbon co-substrates. Produced lipids may include unsaturated C6-C24 fatty acids, alcohols, aldehydes, and acetates which may be useful as final products or precursors to insect pheromones, fragrances, flavors, and polymer intermediates. The application further relates to recombinant microorganisms modified for improved production of biomass or lipid, or improved lipid selectivity. Also provided are methods of producing one or more lipid using the recombinant microorganisms, as well as compositions comprising the recombinant microorganisms and/or optionally one or more of the product lipid.

公开(公告)号：US20220053774A1

公开(公告)日：2022-02-24

申请号：US17408050

申请日：2021-08-20

申请人： Provivi, Inc.

发明人： Effendi LEONARD ,  Peter MEINHOLD ,  Keith WAMPLER ,  Pedro COELHO ,  Micah SHEPPARD ,  Thomas HEEL

IPC分类号： A01N63/50 ,  C12P7/64 ,  A01N31/02 ,  C12N9/02 ,  C12P7/04

摘要： The present application relates to recombinant microorganisms useful in the biosynthesis of unsaturated C6-C24 fatty alcohols, aldehydes, and acetates which may be useful as insect pheromones, fragrances, flavors, and polymer intermediates. The C6-C24 fatty alcohols, aldehydes, and acetates described herein may be used as substrates for metathesis reactions to expand the repertoire of target compounds and pheromones. The application further relates to recombinant microorganisms co-expressing a pheromone pathway and a pathway for the production of a toxic protein, peptide, oligonucleotide, or small molecule suitable for use in an attract-and-kill pest control approach. Also provided are methods of producing unsaturated C6-C24 fatty alcohols, aldehydes, and acetates using the recombinant microorganisms, as well as compositions comprising the recombinant microorganisms and/or optionally one or more of the product alcohols, aldehydes, or acetates.

公开(公告)号：US11214818B2

公开(公告)日：2022-01-04

申请号：US16307282

申请日：2017-06-06

申请人： Provivi, Inc.

发明人： Konrad B. Otte ,  Micah Sheppard ,  Vu Bui ,  Keith M. Wampler ,  Effendi Leonard

IPC分类号： C12P7/64 ,  C07C29/136 ,  C12N1/14 ,  C12N9/02 ,  C12N15/52 ,  C12R1/645

摘要： The present application relates to methods of producing one or more fatty alcohols and/or one or more fatty aldehydes from one or more unsaturated lipid moieties by combining the obtainment or production of the one or more unsaturated lipid moieties from a biological source with conversion by non-biological means of the one or more unsaturated lipid moieties to one or more fatty alcohols and/or one or more fatty aldehydes. The present application also relates to recombinant microorganisms having a biosynthesis pathway for the production of one or more unsaturated lipid moieties. The one or more fatty alcohols can further be chemically converted to one or more corresponding fatty acetates. The one or more fatty alcohols, one or more fatty aldehydes and/or one or more fatty acetates produced by the methods described herein may be one or more insect pheromones, one or more fragrances, one or more flavoring agents, or one or more polymer intermediates.

公开(公告)号：US11856951B2

公开(公告)日：2024-01-02

申请号：US16064024

申请日：2016-12-22

申请人： Provivi, Inc.

发明人： John B. Schoper ,  Pedro Coelho ,  Christopher Wheeler

IPC分类号： A01N37/02

CPC分类号： A01N37/02

摘要： Systems and methods for managing resistance to insecticidal traits and chemicals are provided. In one aspect, systems and methods are provided that: 1) delay the development of resistance to transgenic insecticidal crops and/or chemical insecticides (preemptive strategies), and 2) rescue one or more pests' susceptibility to transgenic insecticidal crops and/or chemical insecticides once pest resistance has developed (responsive strategies).

公开(公告)号：US20230034938A1

公开(公告)日：2023-02-02

申请号：US17408213

申请日：2021-08-20

申请人： Provivi, Inc.

发明人： Micah SHEPPARD ,  Thomas HEEL ,  Peter MEINHOLD ,  Keith WAMPLER ,  Pedro COELHO ,  Effendi LEONARD

IPC分类号： C12P7/64 ,  C12N9/04 ,  C12N9/02 ,  C12N9/10 ,  C12N15/81

摘要： The present application relates to recombinant microorganisms useful in the biosynthesis of unsaturated C6-C24 fatty alcohols, aldehydes, and acetates which may be useful as insect pheromones, fragrances, flavors, and polymer intermediates. The recombinant microorganisms may express enzymes or enzyme variants useful for production of and/or may be modified to downregulate pathways to shunt production toward unsaturated C6-C24 fatty alcohols, aldehydes, and acetates. The C6-C24 fatty alcohols, aldehydes, and acetates described herein may be used as substrates for metathesis reactions to expand the repertoire of target compounds and pheromones. The application further relates to recombinant microorganisms co-expressing a pheromone pathway and a pathway for the production of a toxic protein, peptide, oligonucleotide, or small molecule suitable for use in an attract-and-kill pest control approach. The application further relates to microorganisms modified to express or downregulate enzymes useful for production of unsaturated short chain fatty alcohols, aldehydes, and acetates which may be useful as insect pheromones, fragrances, flavors, and polymer intermediates. Also provided are methods of producing unsaturated C6-C24 fatty alcohols, aldehydes, and acetates using the recombinant microorganisms, as well as compositions comprising the recombinant microorganisms and/or optionally one or more of the product alcohols, aldehydes, or acetates.

公开(公告)号：US20220017449A1

公开(公告)日：2022-01-20

申请号：US17312374

申请日：2019-12-10

申请人： Provivi, Inc.

发明人： Keith M. Wampler ,  Choon Woo Lee ,  David Rozzell

IPC分类号： C07C67/343 ,  C07C45/68 ,  B01J31/24

摘要： Methods for preparing conjugated dienes are described. An α,β-unsaturated E olefin intermediate may be prepared via cross-metathesis using a catalyst comprising a transition metal (e.g., ruthenium), a first carbene ligand (e.g., a substituted indenylidene) and an N-heterocyclic carbene ligand (e.g., an imidazolidinylidene). The catalyst further includes a phenylphosphine ligand, a tri(isopropoxy)phosphine ligand, a dimethylsulfoxide ligand, an acetonitrile ligand, or a pyridine ligand. Following the cross metathesis-step, the α,β-unsaturated aldehyde intermediate may be converted to the conjugated diene product via reaction with a phosphonium ylide. Products obtained via the methods of the disclosure include (7E,9Z)-dodeca-7,9-dien-1-yl acetate, a pheromone produced by Lobesia botrana (European grapevine moth), and other insect pheromones.

公开(公告)号：US11109596B2

公开(公告)日：2021-09-07

申请号：US16420566

申请日：2019-05-23

申请人： Provivi, Inc.

发明人： Effendi Leonard ,  Peter Meinhold ,  Keith Wampler ,  Pedro Coelho ,  Micah Sheppard ,  Thomas Heel

IPC分类号： A01N63/50 ,  C12P7/64 ,  A01N31/02 ,  C12N9/02 ,  C12P7/04

摘要： The present application relates to recombinant microorganisms useful in the biosynthesis of unsaturated C6-C24 fatty alcohols, aldehydes, and acetates which may be useful as insect pheromones, fragrances, flavors, and polymer intermediates. The C6-C24 fatty alcohols, aldehydes, and acetates described herein may be used as substrates for metathesis reactions to expand the repertoire of target compounds and pheromones. The application further relates to recombinant microorganisms co-expressing a pheromone pathway and a pathway for the production of a toxic protein, peptide, oligonucleotide, or small molecule suitable for use in an attract-and-kill pest control approach. Also provided are methods of producing unsaturated C6-C24 fatty alcohols, aldehydes, and acetates using the recombinant microorganisms, as well as compositions comprising the recombinant microorganisms and/or optionally one or more of the product alcohols, aldehydes, or acetates.

公开(公告)号：US20210130270A1

公开(公告)日：2021-05-06

申请号：US17149662

申请日：2021-01-14

申请人： Provivi, Inc.

发明人： Keith M. WAMPLER ,  Choon Woo LEE ,  David ROZZELL

IPC分类号： C07C29/36 ,  C07C67/343 ,  C07C51/09 ,  C07C67/293 ,  C07C253/30 ,  C07C45/44

摘要： Methods for the preparation of alkenes including insect pheromones are described. The methods include homologation reactions employing reagents such as 1,3-diesters, epoxides, cyanoacetates, and cyanide salts for elongation of starting materials and intermediates by one or two carbon atoms. The alkenes include insect pheromones useful in a number of agricultural applications.