Amphiphilic Low-Molecular-Weight Gelators Bearing β-<i>S</i>-<i>N</i>-Acetylglucosamine Linked to a Tartaric Acid Scaffold: Synthesis, Self-Assembly and Wheat Germ Agglutinin Binding
The self-assembly of carbohydrate-based amphiphiles can lead to colloidal soft materials such as supramolecular gels featuring highly desirable characteristics like biodegradability and biocompatibility. The report herein presents the synthesis, characterization and supramolecular self-assembly, phy...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-12-01
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| Series: | Gels |
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| Online Access: | https://www.mdpi.com/2310-2861/10/1/5 |
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| author | Vicente Leafar Peña García Pablo Héctor Di Chenna María Laura Uhrig |
| author_facet | Vicente Leafar Peña García Pablo Héctor Di Chenna María Laura Uhrig |
| author_sort | Vicente Leafar Peña García |
| collection | DOAJ |
| description | The self-assembly of carbohydrate-based amphiphiles can lead to colloidal soft materials such as supramolecular gels featuring highly desirable characteristics like biodegradability and biocompatibility. The report herein presents the synthesis, characterization and supramolecular self-assembly, physical gelation and wheat lectin binding of two structurally related amphiphilic compounds having β-<i>S</i>-<i>N</i>-acetylglucosamine residues linked to a 2,3-diacyl-<i>N</i>,<i>N</i>′-dipropargylated-<span style="font-variant: small-caps;">l</span>-tartaric diamide. A 1-thio-β-<i>N</i>-acetyl-<span style="font-variant: small-caps;">d</span>-glucosamine precursor attached to a conveniently functionalized linker with an azido group was synthesized by means of a one-pot procedure followed by deprotection. A click reaction successfully led to the two amphiphiles, which differed in length of the fatty acid attached to the tartaric acid scaffold. Although both compounds are poorly soluble in water and organic solvents, the difference in terms of hydrophilic moieties provided them with distinct supramolecular gelation properties. While the presence of an octadecyl chain produced a hydrogelator, the dodecadecyl homologue would only form weak gels in DMSO. SEM and rheology experiments confirmed the characteristic fibrillar morphology and viscoelastic properties, in agreement with the presence of physical gels. Both amphiphiles were able to interact reversibly with wheat germ agglutinin (WGA), a lectin that specifically recognizes GlcNAc residues, indicating a potential use in the food industry, as a gluten sensitivity manager, as well as in health-related industries, for example, for drug delivery systems. |
| first_indexed | 2024-03-08T10:54:54Z |
| format | Article |
| id | doaj.art-07179a8f2e08482eb10860cdbfa5d333 |
| institution | Directory Open Access Journal |
| issn | 2310-2861 |
| language | English |
| last_indexed | 2024-03-08T10:54:54Z |
| publishDate | 2023-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Gels |
| spelling | doaj.art-07179a8f2e08482eb10860cdbfa5d3332024-01-26T16:38:27ZengMDPI AGGels2310-28612023-12-01101510.3390/gels10010005Amphiphilic Low-Molecular-Weight Gelators Bearing β-<i>S</i>-<i>N</i>-Acetylglucosamine Linked to a Tartaric Acid Scaffold: Synthesis, Self-Assembly and Wheat Germ Agglutinin BindingVicente Leafar Peña García0Pablo Héctor Di Chenna1María Laura Uhrig2Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Intendente Güiraldes 2160, 3er piso, Pabellón 2, Ciudad Universitaria, Buenos Aires C1428EGA, ArgentinaDepartamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Intendente Güiraldes 2160, 3er piso, Pabellón 2, Ciudad Universitaria, Buenos Aires C1428EGA, ArgentinaDepartamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Intendente Güiraldes 2160, 3er piso, Pabellón 2, Ciudad Universitaria, Buenos Aires C1428EGA, ArgentinaThe self-assembly of carbohydrate-based amphiphiles can lead to colloidal soft materials such as supramolecular gels featuring highly desirable characteristics like biodegradability and biocompatibility. The report herein presents the synthesis, characterization and supramolecular self-assembly, physical gelation and wheat lectin binding of two structurally related amphiphilic compounds having β-<i>S</i>-<i>N</i>-acetylglucosamine residues linked to a 2,3-diacyl-<i>N</i>,<i>N</i>′-dipropargylated-<span style="font-variant: small-caps;">l</span>-tartaric diamide. A 1-thio-β-<i>N</i>-acetyl-<span style="font-variant: small-caps;">d</span>-glucosamine precursor attached to a conveniently functionalized linker with an azido group was synthesized by means of a one-pot procedure followed by deprotection. A click reaction successfully led to the two amphiphiles, which differed in length of the fatty acid attached to the tartaric acid scaffold. Although both compounds are poorly soluble in water and organic solvents, the difference in terms of hydrophilic moieties provided them with distinct supramolecular gelation properties. While the presence of an octadecyl chain produced a hydrogelator, the dodecadecyl homologue would only form weak gels in DMSO. SEM and rheology experiments confirmed the characteristic fibrillar morphology and viscoelastic properties, in agreement with the presence of physical gels. Both amphiphiles were able to interact reversibly with wheat germ agglutinin (WGA), a lectin that specifically recognizes GlcNAc residues, indicating a potential use in the food industry, as a gluten sensitivity manager, as well as in health-related industries, for example, for drug delivery systems.https://www.mdpi.com/2310-2861/10/1/5supramolecular gelamphiphilecarbohydratelectinorganogelhydrogel |
| spellingShingle | Vicente Leafar Peña García Pablo Héctor Di Chenna María Laura Uhrig Amphiphilic Low-Molecular-Weight Gelators Bearing β-<i>S</i>-<i>N</i>-Acetylglucosamine Linked to a Tartaric Acid Scaffold: Synthesis, Self-Assembly and Wheat Germ Agglutinin Binding Gels supramolecular gel amphiphile carbohydrate lectin organogel hydrogel |
| title | Amphiphilic Low-Molecular-Weight Gelators Bearing β-<i>S</i>-<i>N</i>-Acetylglucosamine Linked to a Tartaric Acid Scaffold: Synthesis, Self-Assembly and Wheat Germ Agglutinin Binding |
| title_full | Amphiphilic Low-Molecular-Weight Gelators Bearing β-<i>S</i>-<i>N</i>-Acetylglucosamine Linked to a Tartaric Acid Scaffold: Synthesis, Self-Assembly and Wheat Germ Agglutinin Binding |
| title_fullStr | Amphiphilic Low-Molecular-Weight Gelators Bearing β-<i>S</i>-<i>N</i>-Acetylglucosamine Linked to a Tartaric Acid Scaffold: Synthesis, Self-Assembly and Wheat Germ Agglutinin Binding |
| title_full_unstemmed | Amphiphilic Low-Molecular-Weight Gelators Bearing β-<i>S</i>-<i>N</i>-Acetylglucosamine Linked to a Tartaric Acid Scaffold: Synthesis, Self-Assembly and Wheat Germ Agglutinin Binding |
| title_short | Amphiphilic Low-Molecular-Weight Gelators Bearing β-<i>S</i>-<i>N</i>-Acetylglucosamine Linked to a Tartaric Acid Scaffold: Synthesis, Self-Assembly and Wheat Germ Agglutinin Binding |
| title_sort | amphiphilic low molecular weight gelators bearing β i s i i n i acetylglucosamine linked to a tartaric acid scaffold synthesis self assembly and wheat germ agglutinin binding |
| topic | supramolecular gel amphiphile carbohydrate lectin organogel hydrogel |
| url | https://www.mdpi.com/2310-2861/10/1/5 |
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