Multivalent assembly of a pyrene functionalized thio-N-acetylglucosamine: Synthesis, spectroscopic and WGA binding studies

Montenegro, Hugo Orlando; Chenna, Pablo H. Di; Spagnuolo, Carla; Uhrig, Marı́a Laura

doi:10.1016/j.carres.2019.04.010

Cited by 6 publications

(4 citation statements)

References 27 publications

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“…Interestingly, a higher stereoselectivity towards the β-anomer was observed in the case of the NPhth derivative, in comparison with the acetamido group, a fact that can be easily explained by the stronger anchimeric participation effect of the C-2 substituent in the case of the former derivative. [58,59] This strategy proved to be successful when applied to more complex structures, such as thiodisaccharides, as will be discussed later.…”

Section: Thioglycosylation Reactionsmentioning

confidence: 97%

“…Still, it showed to be convenient as the number of reaction as well as purification steps were sensibly reduced, and also was compatible with both, N ‐acetyl and N ‐phthalimido (NPhth) groups present at C‐2 (Scheme 6). Interestingly, a higher stereoselectivity towards the β‐anomer was observed in the case of the NPhth derivative, in comparison with the acetamido group, a fact that can be easily explained by the stronger anchimeric participation effect of the C‐2 substituent in the case of the former derivative [58,59] …”

Section: General Strategies For the Access To Thiodisaccharides: The Hexnac Challengementioning

confidence: 98%

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Synthesis of Thiodisaccharides Bearing N‐Acetylhexosamine Residues: Challenges, Achievements and Perspectives

Cristófalo

Cano

Uhrig

2021

The Chemical Record

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Carbohydrate-protein interactions are involved in a myriad of biological processes. Thus, glycomimetics have arisen as one of the most promising synthetic targets to that end. Within the broad variety of glycomimetics, thiodisaccharides have proven to be excellent tools to study these processes, and even more, some of them unveiled interesting biological activities. This review brings together research made on the introduction of N-acetylhexosamine residues into thiodisaccharides to date, passing through classic substitution (as S N 2, thioglycosylation and ring-opening reactions) and addition (as thiol-ene coupling and Michael-type additions) reactions. Recent and interesting developments regarding addition reactions to vinyl azides, cross-coupling reactions and novel chemoenzymatic methods are also discussed.

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Section: Thioglycosylation Reactionsmentioning

confidence: 97%

Section: General Strategies For the Access To Thiodisaccharides: The Hexnac Challengementioning

confidence: 98%

Synthesis of Thiodisaccharides Bearing N‐Acetylhexosamine Residues: Challenges, Achievements and Perspectives

Cristófalo

Cano

Uhrig

2021

The Chemical Record

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“…Lectins can reversibly recognize mono-and oligosaccharides with high specificity. They typically contain one carbohydrate recognition domain per monomer, and, via interaction with multivalent carbohydrate systems, they usually form cross-linked networks [19]. This multivalent assembly process is associated with a high affinity increase, the so-called cluster effect [14,37].…”

Section: Wheat Germ Lectin-binding Assaymentioning

confidence: 99%

“…Also, it is certain that WGA is an antinutritional factor involved in several autoimmune gastrointestinal disorders such the celiac disease [17,18]. Our group has recently described several amphiphilic compounds containing GlcNAc and AllNAc based on aromatic scaffolds, which have interacted multivalently with the WGA [19]. Now, regarding self-assembled structures and materials produced from sugar-based low-molecular-weight amphiphiles, it is worth mentioning that supramolecular gels (SG) are of great interest due to their properties as soft materials.…”

Section: Introductionmentioning

confidence: 99%

Amphiphilic Low-Molecular-Weight Gelators Bearing β-S-N-Acetylglucosamine Linked to a Tartaric Acid Scaffold: Synthesis, Self-Assembly and Wheat Germ Agglutinin Binding

Peña García,

Di Chenna,

Uhrig

2023

Gels

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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-S-N-acetylglucosamine residues linked to a 2,3-diacyl-N,N′-dipropargylated-l-tartaric diamide. A 1-thio-β-N-acetyl-d-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.

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Recent trends in synthesis of photoluminescence based pyrene derivatives and their biomaterial applications

Rajasekar,

Bhuvanesh,

Varada

2023

Results in Chemistry

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Multivalent assembly of a pyrene functionalized thio-N-acetylglucosamine: Synthesis, spectroscopic and WGA binding studies

Cited by 6 publications

References 27 publications

Synthesis of Thiodisaccharides Bearing N‐Acetylhexosamine Residues: Challenges, Achievements and Perspectives

Synthesis of Thiodisaccharides Bearing N‐Acetylhexosamine Residues: Challenges, Achievements and Perspectives

Amphiphilic Low-Molecular-Weight Gelators Bearing β-S-N-Acetylglucosamine Linked to a Tartaric Acid Scaffold: Synthesis, Self-Assembly and Wheat Germ Agglutinin Binding

Recent trends in synthesis of photoluminescence based pyrene derivatives and their biomaterial applications

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