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Keywords = propylphosphonic anhydride

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15 pages, 1022 KiB  
Article
Fast Solution-Phase and Liquid-Phase Peptide Syntheses (SolPSS and LPPS) Mediated by Biomimetic Cyclic Propylphosphonic Anhydride (T3P®)
by Alexia Mattellone, Dario Corbisiero, Paolo Cantelmi, Giulia Martelli, Chiara Palladino, Alessandra Tolomelli, Walter Cabri and Lucia Ferrazzano
Molecules 2023, 28(20), 7183; https://doi.org/10.3390/molecules28207183 - 19 Oct 2023
Cited by 2 | Viewed by 6443
Abstract
The growing applications of peptide-based therapeutics require the development of efficient protocols from the perspective of an industrial scale-up. T3P® (cyclic propylphosphonic anhydride) promotes amidation in the solution-phase through a biomimetic approach, similar to the activation of carboxylic moiety catalyzed by ATP-grasp [...] Read more.
The growing applications of peptide-based therapeutics require the development of efficient protocols from the perspective of an industrial scale-up. T3P® (cyclic propylphosphonic anhydride) promotes amidation in the solution-phase through a biomimetic approach, similar to the activation of carboxylic moiety catalyzed by ATP-grasp enzymes in metabolic pathways. The T3P® induced coupling reaction was applied in this study to the solution-phase peptide synthesis (SolPPS). Peptide bond formation occurred in a few minutes with high efficiency and no epimerization, generating water-soluble by-products, both using N-Boc or N-Fmoc amino acids. The optimized protocol, which was successfully applied to the iterative synthesis of a pentapeptide, also allowed for a decrease in the solvent volume, thus improving process sustainability. The protocol was finally extended to the liquid-phase peptide synthesis (LPPS), where the isolation of the peptide was performed using precipitation, thus also showing the suitability of this coupling reagent to this emerging technique. Full article
(This article belongs to the Special Issue Peptide and Peptidomimetic: Synthesis, Purification and Characterization)
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13 pages, 1361 KiB  
Article
Study of the Three-Component Reactions of 2-Alkynylbenzaldehydes, Aniline, and Dialkyl Phosphites—The Significance of the Catalyst System
by Nóra Popovics-Tóth, Kármen Emőke Szabó and Erika Bálint
Materials 2021, 14(20), 6015; https://doi.org/10.3390/ma14206015 - 13 Oct 2021
Cited by 2 | Viewed by 2030
Abstract
New, practical approaches for the synthesis of α-amino (2-alkynylphenyl)-methylphosphonates and 1,2-dihydroisoquinolin-1-ylphosphonates were developed. By the propylphosphonic anhydride (T3P®)-mediated Kabachnik–Fields reaction of 2-alkynylbenzaldehydes, aniline, and dialkyl phosphites, α-amino (2-alkynylphenyl)-methylphosphonates were obtained selectively in high yields. The method developed is a [...] Read more.
New, practical approaches for the synthesis of α-amino (2-alkynylphenyl)-methylphosphonates and 1,2-dihydroisoquinolin-1-ylphosphonates were developed. By the propylphosphonic anhydride (T3P®)-mediated Kabachnik–Fields reaction of 2-alkynylbenzaldehydes, aniline, and dialkyl phosphites, α-amino (2-alkynylphenyl)-methylphosphonates were obtained selectively in high yields. The method developed is a simple operation and did not require a chromatographic separation since the products could be isolated from the reaction mixture by a simple extraction. At the same time, 2,3-disubstituted-1,2-dihydroisoquinolin-1-ylphosphonates could be prepared effectively from the same kinds of starting materials (2-alkynylbenzaldehydes, aniline, and dialkyl phosphites) at 60 °C in a short reaction time by changing the catalyst for CuCl. Therefore, it was proved that the catalyst system applied played a crucial role with respect to the reaction outcome. Full article
(This article belongs to the Special Issue Advances in Organocatalysts: Synthesis and Applications)
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15 pages, 3494 KiB  
Article
Hyaluronic Acid Functionalization with Jeffamine® M2005: A Comparison of the Thermo-Responsiveness Properties of the Hydrogel Obtained through Two Different Synthesis Routes
by Mathieu Madau, Didier Le Cerf, Virginie Dulong and Luc Picton
Gels 2021, 7(3), 88; https://doi.org/10.3390/gels7030088 - 9 Jul 2021
Cited by 9 | Viewed by 3707
Abstract
Hyaluronic acid (HA) of different molar masses (respectively 38,000, 140,000 and 1,200,000 g.mol−1) have been functionalized with a commercial poly(etheramine), Jeffamine® M2005, in order to devise physical thermo-responsive hydrogels. Two routes have been studied, involving the use of either water [...] Read more.
Hyaluronic acid (HA) of different molar masses (respectively 38,000, 140,000 and 1,200,000 g.mol−1) have been functionalized with a commercial poly(etheramine), Jeffamine® M2005, in order to devise physical thermo-responsive hydrogels. Two routes have been studied, involving the use of either water for the first one or of N,N′-Dimethylformamide (DMF), a polar aprotic solvent, for the second one. In the case of the water route, the reaction was performed using a mixture of N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide (EDC) and N-hydroxysuccinimide (NHS) as coupling reagents. The reaction was optimized while making sure no free M2005 remained in the final material, leading to M2005 grafting degrees of about 4%, which enabled the formation of hydrogels by increasing the temperature. In the case of the organic solvent route, propylphosphonic anhydride T3P® was used as a coupling reagent in DMF, resulting in a M2005 grafting degree of around 8% with better thermo-responsive properties of HA-g-M2005 compared to those obtained when the reaction was performed in water. However, the reaction systematically led to covalent cross-linking in the case of the HA, with the highest starting molar masses resulting in a very different rheological behaviour and with higher gel strength retaining thermo-responsive behaviour but being only poorly soluble in water. Full article
(This article belongs to the Special Issue Gels Horizons: From Science to Smart Materials)
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13 pages, 2329 KiB  
Article
Synthesis of Naphthoxazinones in a One-Pot Two-Step Manner by the Application of Propylphosphonic Anhydride (T3P®)
by Valentina Varga, Péter Ábrányi-Balogh and Mátyás Milen
Chemistry 2020, 2(2), 600-612; https://doi.org/10.3390/chemistry2020037 - 16 Jun 2020
Cited by 2 | Viewed by 4950
Abstract
A sequential one-pot two-step protocol has been elaborated for the synthesis of naphthoxazinones from 2-naphthol, methyl carbamate, and aromatic aldehydes. First, a three-component reaction was optimized with the dehydrating additive propylphosphonic anhydride (T3P®), resulting in 1-carbamatoalkyl 2-naphthols in good to excellent [...] Read more.
A sequential one-pot two-step protocol has been elaborated for the synthesis of naphthoxazinones from 2-naphthol, methyl carbamate, and aromatic aldehydes. First, a three-component reaction was optimized with the dehydrating additive propylphosphonic anhydride (T3P®), resulting in 1-carbamatoalkyl 2-naphthols in good to excellent yields. Following the successful multicomponent approach, intramolecular acylation was performed at high temperature, again with the contribution of T3P®, resulting in naphthoxazinone derivatives in moderate yields. These two steps were optimized together in one-pot as well, and the sequential rise in the requisite temperature eventuated the optimal procedure for the multistep cascade. Full article
(This article belongs to the Special Issue Organic Chemistry Research in Hungary)
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3 pages, 154 KiB  
Short Note
N-(2-Chloro-5-cyanophenyl)-4,4,4-trifluorobutanamide
by Karikere Ekanna Manojkumar, Swamy Sreenivasa, Govindaiah Shivaraja and Tadimety Madhu Chakrapani Rao
Molbank 2013, 2013(3), M803; https://doi.org/10.3390/M803 - 28 Jun 2013
Cited by 5 | Viewed by 4887
Abstract
N-(2-Chloro-5-cyanophenyl)-4,4,4-trifluorobutanamide (3) was synthesized by reacting 4,4,4-trifluorobutanoic acid (1) with 2-amino-4-chlorobenzonitrile (2) in the presence of triethylamine and propylphosphonic anhydride in ethyl acetate. Character­ization of the compound was done by IR, 1H-NMR, 13C-NMR, LC-MS and CHN analysis. Full article
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