The Importance of Reaction Conditions on the Chemical Structure of <i>N</i>,<i>O</i>-Acylated Chitosan Derivatives
The structure of acylated chitosan derivatives strongly determines the properties of obtained products, influencing their hydrodynamic properties and thereby their solubility or self-assembly susceptibility. In the present work, the significance of slight changes in acylation conditions on the struc...
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MDPI AG
2019-08-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/17/3047 |
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| author | Agnieszka Piegat Agata Goszczyńska Tomasz Idzik Agata Niemczyk |
| author_facet | Agnieszka Piegat Agata Goszczyńska Tomasz Idzik Agata Niemczyk |
| author_sort | Agnieszka Piegat |
| collection | DOAJ |
| description | The structure of acylated chitosan derivatives strongly determines the properties of obtained products, influencing their hydrodynamic properties and thereby their solubility or self-assembly susceptibility. In the present work, the significance of slight changes in acylation conditions on the structure and properties of the products is discussed. A series of chitosan-acylated derivatives was synthesized by varying reaction conditions in a two-step process. As reaction media, two diluted acid solutions—i.e., acetic acid and hydrochloric acid)—and two coupling systems—i.e., 1-ethyl-3-(3-dimethyl-aminopropyl)-1-carbodiimide hydrochloride (EDC) and <i>N</i>−hydroxysulfosuccinimide (EDC/NHS)—were used. The chemical structure of the derivatives was studied in detail by means of two spectroscopic methods, namely infrared and nuclear magnetic resonance spectroscopy, in order to analyze the preference of the systems towards <i>N</i>- or <i>O</i>-acylation reactions, depending on the synthesis conditions used. The results obtained from advanced <sup>1</sup>H-<sup>13</sup>C HMQC spectra emphasized the challenge of achieving a selective acylation reaction path. Additionally, the study of the molecular weight and solution behavior of the derivatives revealed that even slight changes in their chemical structure have an important influence on their final properties. Therefore, an exact knowledge of the obtained structure of derivatives is essential to achieve reaction reproducibility and to target the application. |
| first_indexed | 2024-12-13T08:31:18Z |
| format | Article |
| id | doaj.art-4fb095a021f244e09a248b0f79c1e9be |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-13T08:31:18Z |
| publishDate | 2019-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-4fb095a021f244e09a248b0f79c1e9be2022-12-21T23:53:45ZengMDPI AGMolecules1420-30492019-08-012417304710.3390/molecules24173047molecules24173047The Importance of Reaction Conditions on the Chemical Structure of <i>N</i>,<i>O</i>-Acylated Chitosan DerivativesAgnieszka Piegat0Agata Goszczyńska1Tomasz Idzik2Agata Niemczyk3West Pomeranian University of Technology Szczecin, Faculty of Chemical Technology and Engineering, Polymer Institute, Division of Functional Materials and Biomaterials, 45 Piastow Ave, 70-311 Szczecin, PolandWest Pomeranian University of Technology Szczecin, Faculty of Chemical Technology and Engineering, Polymer Institute, Division of Functional Materials and Biomaterials, 45 Piastow Ave, 70-311 Szczecin, PolandWest Pomeranian University of Technology Szczecin, Faculty of Chemical Technology and Engineering, Department of Organic and Physical Chemistry, 42 Piastow Ave, 71-065 Szczecin, PolandWest Pomeranian University of Technology Szczecin, Faculty of Chemical Technology and Engineering, Polymer Institute, Division of Functional Materials and Biomaterials, 45 Piastow Ave, 70-311 Szczecin, PolandThe structure of acylated chitosan derivatives strongly determines the properties of obtained products, influencing their hydrodynamic properties and thereby their solubility or self-assembly susceptibility. In the present work, the significance of slight changes in acylation conditions on the structure and properties of the products is discussed. A series of chitosan-acylated derivatives was synthesized by varying reaction conditions in a two-step process. As reaction media, two diluted acid solutions—i.e., acetic acid and hydrochloric acid)—and two coupling systems—i.e., 1-ethyl-3-(3-dimethyl-aminopropyl)-1-carbodiimide hydrochloride (EDC) and <i>N</i>−hydroxysulfosuccinimide (EDC/NHS)—were used. The chemical structure of the derivatives was studied in detail by means of two spectroscopic methods, namely infrared and nuclear magnetic resonance spectroscopy, in order to analyze the preference of the systems towards <i>N</i>- or <i>O</i>-acylation reactions, depending on the synthesis conditions used. The results obtained from advanced <sup>1</sup>H-<sup>13</sup>C HMQC spectra emphasized the challenge of achieving a selective acylation reaction path. Additionally, the study of the molecular weight and solution behavior of the derivatives revealed that even slight changes in their chemical structure have an important influence on their final properties. Therefore, an exact knowledge of the obtained structure of derivatives is essential to achieve reaction reproducibility and to target the application.https://www.mdpi.com/1420-3049/24/17/3047acylation reactionchitosan derivativesEDC/NHS coupling systemfatty acidsspectroscopic methods |
| spellingShingle | Agnieszka Piegat Agata Goszczyńska Tomasz Idzik Agata Niemczyk The Importance of Reaction Conditions on the Chemical Structure of <i>N</i>,<i>O</i>-Acylated Chitosan Derivatives Molecules acylation reaction chitosan derivatives EDC/NHS coupling system fatty acids spectroscopic methods |
| title | The Importance of Reaction Conditions on the Chemical Structure of <i>N</i>,<i>O</i>-Acylated Chitosan Derivatives |
| title_full | The Importance of Reaction Conditions on the Chemical Structure of <i>N</i>,<i>O</i>-Acylated Chitosan Derivatives |
| title_fullStr | The Importance of Reaction Conditions on the Chemical Structure of <i>N</i>,<i>O</i>-Acylated Chitosan Derivatives |
| title_full_unstemmed | The Importance of Reaction Conditions on the Chemical Structure of <i>N</i>,<i>O</i>-Acylated Chitosan Derivatives |
| title_short | The Importance of Reaction Conditions on the Chemical Structure of <i>N</i>,<i>O</i>-Acylated Chitosan Derivatives |
| title_sort | importance of reaction conditions on the chemical structure of i n i i o i acylated chitosan derivatives |
| topic | acylation reaction chitosan derivatives EDC/NHS coupling system fatty acids spectroscopic methods |
| url | https://www.mdpi.com/1420-3049/24/17/3047 |
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