AR060392A1 - Procesos para la sintesis quimica de lipoquitooligosacaridos, intermediarios de esos procesos y composiciones que los contienen. - Google Patents
Procesos para la sintesis quimica de lipoquitooligosacaridos, intermediarios de esos procesos y composiciones que los contienen.Info
- Publication number
- AR060392A1 AR060392A1 ARP070101488A ARP070101488A AR060392A1 AR 060392 A1 AR060392 A1 AR 060392A1 AR P070101488 A ARP070101488 A AR P070101488A AR P070101488 A ARP070101488 A AR P070101488A AR 060392 A1 AR060392 A1 AR 060392A1
- Authority
- AR
- Argentina
- Prior art keywords
- groups
- mixture
- product
- processes
- mono
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/06—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/12—Acyclic radicals, not substituted by cyclic structures attached to a nitrogen atom of the saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
- C07H13/06—Fatty acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/14—Acyclic radicals, not substituted by cyclic structures attached to a sulfur, selenium or tellurium atom of a saccharide radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Biotechnology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Saccharide Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Cultivation Of Plants (AREA)
- Pretreatment Of Seeds And Plants (AREA)
Abstract
Procesos para la síntesis de lipoquitooligosacáridos. Se prepara un precursor de oligoglucosamina totalmente acilado y se hace reaccionar con un monomero de glucosamina que tiene un grupo ftaloilo protector de aminas. Con la eliminacion del grupo ftaloilo, se puede agregar un ácido graso a la unidad de glucosamina terminal, formando un Iipoquitooligosacárido. Los procesos se pueden adaptar para usarse a escala comercial. Reivindicacion 1: Un proceso para sintetizar un compuesto Iipoquitooligosacárido que tiene la estructura A en donde los grupos individuales R1, R2 y R3 se seleccionan independientemente entre H y grupos alquilo, arilo, aralquilo, mono, di o polialquenilo, mono, di o polialquinilo C1-20; R4 se selecciona entre un monosacárido, sulfato y fosfato; y n es entre 0 y aproximadamente 20; caracterizado porque comprende: a) combinar un compuesto de estructura C en donde R1 se selecciona entre H, grupos alquilo, arilo y aralquilo C1-20, con un compuesto de estructura B donde los grupos individuales R1 y R2 se seleccionan independientemente entre H y grupos alquilo, arilo y aralquilo C1-20; R4 se selecciona entre un monosacárido, un sulfato y un fosfato; y n es entre 0 y aproximadamente 19; en un solvente aprotico y agitando la solucion a una temperatura entre aproximadamente de 0°C y aproximadamente de -78°C para formar una primera mezcla; b) agregar a la mezcla de a) un primer agente activante que se selecciona entre N-haloimidas para formar una segunda mezcla; c) agregar un segundo agente activante que se selecciona entre ácidos perfluoroalquilsulfonicos, y opcionalmente agregar un reactivo que se selecciona entre sulfonatos de metilperfluoroalquilos a la segunda mezcla para formar una tercera mezcla; d) hacer reaccionar la tercera mezcla a una temperatura de entre aproximadamente de 0°C y aproximadamente de -78°C para formar un producto que comprende grupos ésteres y un grupo N-ftalimido; e) aislar el producto de d); f) eliminar los grupos ésteres y el grupo N-ftalimido del producto aislado de e) con lo que se forma un producto de-esterificado y des-N-ftalimidado; g) aislar el producto de f); h) hacer reaccionar en forma selectiva el grupo amino de la unidad de azucar terminal del producto aislado de g) con un ácido o un halogenuro de ácido de formula R1COX: en donde X = OH o un halogeno, para los ácidos y los halogenuros de ácidos, respectivamente, y R1 se selecciona entre H, grupos alquilo, arilo, aralquilo, mono, di o polialquenilo, mono, di o polialquinilo C1-20 para formar un lipoquitooligosacárido; y i) aislar el lipoquitooligosacárido.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US79042906P | 2006-04-07 | 2006-04-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR060392A1 true AR060392A1 (es) | 2008-06-11 |
Family
ID=38521085
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP070101488A AR060392A1 (es) | 2006-04-07 | 2007-04-09 | Procesos para la sintesis quimica de lipoquitooligosacaridos, intermediarios de esos procesos y composiciones que los contienen. |
Country Status (9)
| Country | Link |
|---|---|
| US (4) | US20070238872A1 (es) |
| EP (3) | EP2348027B1 (es) |
| JP (1) | JP2009533345A (es) |
| KR (1) | KR20090023563A (es) |
| CN (1) | CN101421287A (es) |
| AR (1) | AR060392A1 (es) |
| AU (1) | AU2007235408A1 (es) |
| CA (1) | CA2644172A1 (es) |
| WO (1) | WO2007117500A2 (es) |
Families Citing this family (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9249265B1 (en) | 2014-09-08 | 2016-02-02 | Sirrus, Inc. | Emulsion polymers including one or more 1,1-disubstituted alkene compounds, emulsion methods, and polymer compositions |
| US9828324B2 (en) | 2010-10-20 | 2017-11-28 | Sirrus, Inc. | Methylene beta-diketone monomers, methods for making methylene beta-diketone monomers, polymerizable compositions and products formed therefrom |
| US10414839B2 (en) | 2010-10-20 | 2019-09-17 | Sirrus, Inc. | Polymers including a methylene beta-ketoester and products formed therefrom |
| US9279022B1 (en) | 2014-09-08 | 2016-03-08 | Sirrus, Inc. | Solution polymers including one or more 1,1-disubstituted alkene compounds, solution polymerization methods, and polymer compositions |
| CN102532207B (zh) * | 2010-12-24 | 2014-11-26 | 大连中科格莱克生物科技有限公司 | 一类n-不饱和脂肪酸酰化壳寡糖及其制备和应用 |
| RU2587047C2 (ru) | 2011-09-08 | 2016-06-10 | Новозимс Биоаг А/С | Способы обработки семян и композиции |
| WO2013040366A1 (en) | 2011-09-14 | 2013-03-21 | Novozymes Biologicals Holdings A/S | Use of lipochito-oligosaccharides and/or chito oligosaccharides in combination with phosphate-solubilizing microorganisms to enhance plant growth |
| US9055747B2 (en) | 2011-09-23 | 2015-06-16 | Novozymes Bioag A/S | Chitooligosaccharides and methods for use in enhancing corn growth |
| WO2013044214A1 (en) | 2011-09-23 | 2013-03-28 | Novozymes Biologicals Holdings A/S | Combinations of lipo-chitooligosaccharides and methods for use in enhancing plant growth |
| BR112014006914A2 (pt) | 2011-09-23 | 2017-04-11 | Novozymes Bioag As | método para intensificar o crescimento de plantas de soja |
| US9055746B2 (en) | 2011-09-23 | 2015-06-16 | Novozymes Bioag A/S | Chitooligosaccharides and methods for use in enhancing plant growth |
| US9221739B2 (en) | 2011-10-19 | 2015-12-29 | Sirrus, Inc. | Methylene beta-diketone monomers, methods for making methylene beta-diketone monomers, polymerizable compositions and products formed therefrom |
| CA2889947A1 (en) * | 2012-10-29 | 2014-05-08 | Pioneer Hi-Bred International, Inc. | Use of glucosamine amides as plant growth and yield enhancers |
| WO2014120799A1 (en) * | 2013-01-31 | 2014-08-07 | Pioneer Hi-Bred International, Inc. | Synthetic lipochitooligosaccharides for improvement of plant growth and yield |
| US20160007600A1 (en) | 2013-03-06 | 2016-01-14 | E.I. Du Pont De Nemours And Company | Synthetic lipochitooligosaccharide analogs for enhancing plant performance |
| MX2017000890A (es) | 2014-07-23 | 2017-05-01 | Novozymes Bioag As | Composiciones que contienen lipo-quitooligosacarido y microorganismo para potenciar el crecimiento de las plantas. |
| US9416091B1 (en) | 2015-02-04 | 2016-08-16 | Sirrus, Inc. | Catalytic transesterification of ester compounds with groups reactive under transesterification conditions |
| US9315597B2 (en) | 2014-09-08 | 2016-04-19 | Sirrus, Inc. | Compositions containing 1,1-disubstituted alkene compounds for preparing polymers having enhanced glass transition temperatures |
| US10501400B2 (en) | 2015-02-04 | 2019-12-10 | Sirrus, Inc. | Heterogeneous catalytic transesterification of ester compounds with groups reactive under transesterification conditions |
| AR105480A1 (es) * | 2015-04-22 | 2017-10-11 | Monsanto Technology Llc | Beneficios de rendimiento de plantas por microbianos |
| EP3498723A1 (en) | 2015-07-30 | 2019-06-19 | Microbial Chemistry Research Foundation | New effective aminoglycoside antibiotic for multidrug-resistant bacteria |
| UA125897C2 (uk) | 2015-09-11 | 2022-07-06 | Новозімес Біоаґ А/С | Стабільна композиція з інокулянтом і спосіб її одержання |
| CA3007111A1 (en) | 2015-12-28 | 2017-07-06 | Novozymes Bioag A/S | Stable inoculant compositions and methods for producing same |
| CA3007102A1 (en) | 2015-12-28 | 2017-07-06 | Novozymes Bioag A/S | Stable inoculant compositions and methods for producing same |
| BR112018074605A2 (pt) | 2016-05-31 | 2019-03-19 | Novozymes Bioag As | composição inoculante líquida, semente de planta revestida, kit, método, e, uso de um composto |
| WO2017210163A1 (en) | 2016-05-31 | 2017-12-07 | Novozymes Bioag A/S | Stable inoculant compositions and methods for producing same |
| US10196481B2 (en) | 2016-06-03 | 2019-02-05 | Sirrus, Inc. | Polymer and other compounds functionalized with terminal 1,1-disubstituted alkene monomer(s) and methods thereof |
| US10428177B2 (en) | 2016-06-03 | 2019-10-01 | Sirrus, Inc. | Water absorbing or water soluble polymers, intermediate compounds, and methods thereof |
| US9617377B1 (en) | 2016-06-03 | 2017-04-11 | Sirrus, Inc. | Polyester macromers containing 1,1-dicarbonyl-substituted 1 alkenes |
| US9567475B1 (en) | 2016-06-03 | 2017-02-14 | Sirrus, Inc. | Coatings containing polyester macromers containing 1,1-dicarbonyl-substituted 1 alkenes |
| WO2018118740A1 (en) | 2016-12-20 | 2018-06-28 | Novozymes Bioag A/S | Stable inoculant compositions and methods for producing same |
| EP3565397A4 (en) | 2017-01-03 | 2020-06-24 | Monsanto Technology LLC | MICROBIAL COMPOSITIONS AND METHODS |
| CA3048997A1 (en) | 2017-01-03 | 2018-07-12 | Monsanto Technology Llc | Microbial compositions and methods |
| EP3565886A1 (en) | 2017-01-04 | 2019-11-13 | Novozymes BioAG A/S | Bacillus isolates and uses thereof |
| CA3048903A1 (en) | 2017-01-05 | 2018-07-12 | Novozymes Bioag A/S | Lysinibacillus isolates and uses thereof |
| US11089776B2 (en) | 2017-02-28 | 2021-08-17 | Monsanto Technology Llc | Containerized liquid formulations |
| WO2018175677A1 (en) | 2017-03-24 | 2018-09-27 | Novozymes Bioag A/S | Combinations of yersinia entomophaga and pesticides or other substances |
| CN107081110B (zh) * | 2017-04-06 | 2019-01-11 | 扬州大学 | 一种部分接枝的壳寡糖表面活性剂及制备方法 |
| CA3064437A1 (en) | 2017-05-26 | 2018-11-29 | Novozymes Bioag A/S | Stable liquid inoculant compositions comprising dodecane |
| UA127377C2 (uk) | 2017-05-26 | 2023-08-02 | Новозімес Біоаґ А/С | Стабільні композиції з інокулянтом, які містять парафінові масла/воски |
| WO2018218035A1 (en) | 2017-05-26 | 2018-11-29 | Novozymes Bioag A/S | Stable inoculant compositions comprising methylated plant oils |
| WO2019006226A1 (en) | 2017-06-29 | 2019-01-03 | Monsanto Technology Llc | METHOD FOR TREATING SEEDS FOR LARGE VOLUMES OF LIQUID |
| BR112020004700A2 (pt) | 2017-09-12 | 2020-09-15 | Monsanto Technology Llc | processos para preparação de sementes tratadas |
| EP3737236A1 (en) | 2018-01-08 | 2020-11-18 | Novozymes BioAG A/S | Aqueous compositions comprising solubilzed lipo-chitooligosaccharides |
| WO2019147660A1 (en) | 2018-01-23 | 2019-08-01 | Novozymes Bioag A/S | Method of enhancing seed germination under abiotic stress with chitin oligosaccharides |
| BR112020022581A2 (pt) | 2018-05-07 | 2021-02-09 | Novozymes Bioag A/S | estirpe isolada de microbacterium trichothecenolyticum, cultura biologicamente pura, uso de uma microbacterium trichothecenolyticum, métodos, composição inoculante, composição de semente não ocorrendo naturalmente, consórcio microbiano sintético, e, uso do consórcio microbiano sintético. |
| CA3144598A1 (en) | 2019-06-24 | 2020-12-30 | Auburn University | A bacillus strain and methods of its use for plant growth promotion |
| JP7513291B2 (ja) | 2019-06-24 | 2024-07-09 | 国立研究開発法人農業・食品産業技術総合研究機構 | エルウィニア属分離株およびその利用 |
| EP3818829A3 (en) | 2019-10-16 | 2021-07-21 | Monsanto Technology LLC | Granular nematicide compositions |
| WO2021086695A1 (en) | 2019-10-29 | 2021-05-06 | Novozymes Bioag A/S | Microbacterium isolates and uses thereof |
| WO2021101937A1 (en) | 2019-11-20 | 2021-05-27 | Novozymes Bioag A/S | Pseudomonas isolates and uses thereof |
| CA3158954A1 (en) | 2019-11-22 | 2021-05-27 | Novozymes Bioag A/S | Paenibacillus isolates and uses thereof |
| WO2022125639A1 (en) | 2020-12-08 | 2022-06-16 | Monsanto Technology Llc | Modified plant-associated bacteria and methods of their use |
| CN115215910B (zh) * | 2022-03-15 | 2024-06-18 | 山东京博农化科技股份有限公司 | 一种聚合度可控的壳寡糖化学合成方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2660658A1 (fr) * | 1990-04-06 | 1991-10-11 | Centre Nat Rech Scient | Substances de structure oligosaccharidique propres a jouer le role de signaux symbiotiques plantes-specifiques, leurs procedes de production et leurs applications. |
| DE19633502A1 (de) * | 1996-08-20 | 1998-02-26 | Bayer Ag | Verwendung von Lipo-Chitooligosacchariden zur Verbesserung der Wirksamkeit von Fungiziden |
| CA2243669A1 (en) | 1998-07-21 | 2000-01-21 | Bios Agriculture Inc. | Composition for accelerating plant seed germination, plant growth and methods using same |
| FR2864538B1 (fr) | 2003-12-30 | 2006-03-03 | Bayer Cropscience Sa | Composes synthetiques utiles comme facteurs de nodulation des plantes legumineuses et procedes de preparation de tels composes |
| CN101203230A (zh) * | 2005-04-01 | 2008-06-18 | 克里斯托弗·理查德·帕里什 | 用nod因子例如葡糖胺寡糖调节血管发生 |
| WO2007001282A2 (en) * | 2005-06-16 | 2007-01-04 | E.I. Dupont De Nemours And Company | Low molecular weight polyglucosamines and polygalactosamines |
| US7485718B2 (en) | 2005-06-16 | 2009-02-03 | E. I. Du Pont De Nemours And Company | Chemical synthesis of low molecular weight polyglucosamines and polygalactosamines |
| WO2010049751A1 (en) * | 2008-10-29 | 2010-05-06 | Institut National De La Recherche Agronomique | Lipochitooligosaccharides stimulating arbuscular mycorrhizal symbiosis |
-
2007
- 2007-04-05 WO PCT/US2007/008379 patent/WO2007117500A2/en active Application Filing
- 2007-04-05 AU AU2007235408A patent/AU2007235408A1/en not_active Abandoned
- 2007-04-05 JP JP2009504276A patent/JP2009533345A/ja active Pending
- 2007-04-05 EP EP11002963.4A patent/EP2348027B1/en not_active Not-in-force
- 2007-04-05 KR KR1020087027225A patent/KR20090023563A/ko not_active Application Discontinuation
- 2007-04-05 EP EP07754836A patent/EP2010552B1/en not_active Not-in-force
- 2007-04-05 CN CNA2007800114829A patent/CN101421287A/zh active Pending
- 2007-04-05 EP EP11002962A patent/EP2348028B1/en not_active Not-in-force
- 2007-04-05 CA CA002644172A patent/CA2644172A1/en not_active Abandoned
- 2007-04-06 US US11/784,253 patent/US20070238872A1/en not_active Abandoned
- 2007-04-09 AR ARP070101488A patent/AR060392A1/es not_active Application Discontinuation
-
2009
- 2009-05-07 US US12/436,938 patent/US8049002B2/en not_active Expired - Fee Related
-
2011
- 2011-09-16 US US13/234,436 patent/US20120004401A1/en not_active Abandoned
-
2014
- 2014-06-19 US US14/308,735 patent/US9090644B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20090292115A1 (en) | 2009-11-26 |
| US9090644B2 (en) | 2015-07-28 |
| WO2007117500A2 (en) | 2007-10-18 |
| EP2348027B1 (en) | 2013-10-23 |
| EP2348027A1 (en) | 2011-07-27 |
| KR20090023563A (ko) | 2009-03-05 |
| WO2007117500A3 (en) | 2008-04-03 |
| JP2009533345A (ja) | 2009-09-17 |
| US20140303361A1 (en) | 2014-10-09 |
| AU2007235408A1 (en) | 2007-10-18 |
| US20120004401A1 (en) | 2012-01-05 |
| EP2348028B1 (en) | 2012-08-22 |
| US20070238872A1 (en) | 2007-10-11 |
| CA2644172A1 (en) | 2007-10-18 |
| EP2010552B1 (en) | 2011-07-06 |
| US8049002B2 (en) | 2011-11-01 |
| EP2010552A2 (en) | 2009-01-07 |
| EP2348028A1 (en) | 2011-07-27 |
| CN101421287A (zh) | 2009-04-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA | Abandonment or withdrawal |