In this study we synthesized two series of 4,6-O-benzylidene acetal protected β-1,2,3-triazolyl glycoside of D-glucose and N-acetyl D-glucosamine derivatives and evaluated their self-assembling properties in a few solvents. 2017 Aug 15;33(32):8076-8089. doi: 10.1021/acs.langmuir.7b01592. The dual role of the benzylidene acetal, as a protecting group and source of carboxylic acid, was exploited in the efficient synthesis of six‐carbon sialic acid analogues and disaccharides bearing uronic acids, including glycosaminoglycan analogues. Epub 2018 Oct 31. Get the latest research from NIH: https://www.nih.gov/coronavirus. But further acetylation of these compounds resulted in loss of gelation properties.  |  In this study we synthesized two series of 4,6-O-benzylidene acetal protected β-1,2,3-triazolyl glycoside of D-glucose and N-acetyl D-glucosamine derivatives and evaluated their self-assembling properties in a few solvents. Synthesis and self-assembly of 1-deoxyglucose derivatives as low molecular weight organogelators. Synthesis and characterization of pH responsive D-glucosamine based molecular gelators. Beilstein J Org Chem. Selective functionalization of common monosaccharides has resulted in several classes of effective LMWGs. Sugar based low molecular weight gelators (LMWGs) are useful small molecules that can form reversible supramolecular gels with many applications. Gels. They arise from the reaction of a 1,2- or 1,3-diols with benzaldehyde. Langmuir. Goyal N, Mangunuru HP, Parikh B, Shrestha S, Wang G. Beilstein J Org Chem. The gels were characterized using optical microscopy, rheology, and FTIR spectroscopy. Several gelators were obtained and the gelation properties of these compounds rely on the structures of the 4-triazolyl substituents. 2016 Apr 1;2(2):13. doi: 10.3390/gels2020013. COVID-19 is an emerging, rapidly evolving situation. Using UV spectroscopy, we found that naproxen was slowly released from the gel to aqueous solution. Other aromatic aldehydes are also used. 2011 Feb 21;7:234-42. doi: 10.3762/bjoc.7.31.  |  Gels. A regioselective reductive ring opening of benzylidene acetals in carbohydrate derivatives using triethylsilane and molecular iodine is fast and compatible with most of the functional groups encountered in oligosaccharide synthesis, and offers excellent yields. Benzylidene acetal; D-glucosamine; D-glucose; Hydrogelator; Organogelator; Self-assembling; Triazole. 2014 Dec 23;10:3111-21. doi: 10.3762/bjoc.10.328. Published by Elsevier Ltd. NLM USA.gov. Carbohydrate Derived Organogelators and the Corresponding Functional Gels Developed in Recent Time. Get the latest public health information from CDC: https://www.coronavirus.gov. HHS 2018 May 30;4(2):52. doi: 10.3390/gels4020052. Chem Asian J.  |  NIH 2018 Dec 18;13(24):3777-3789. doi: 10.1002/asia.201801161. eCollection 2014. Recently we found that certain peracetylated sugars containing anomeric triazole functional groups were effective gelators. We also analyzed the molecular assemblies, using 1H NMR spectroscopy to probe the influences of the hydroxyl, amide, and triazole functional groups. Please enable it to take advantage of the complete set of features! Typically, alkyl derivatives resulted in effective gelation in organic solvents and aqueous mixtures of ethanol and dimethyl sulfoxide. Low-Molecular-Weight Gelators as Base Materials for Ointments. National Center for Biotechnology Information, Unable to load your collection due to an error, Unable to load your delegates due to an error. Keywords: The reaction conditions are equally effective in thioglycosides. These compounds can also be oxidized to carboxylic acids in order to open important biological molecules, such as glycosaminoglycans, to other routes of synthesis. Several gelators were obtained and the gelation properties of these compounds rely on the structures of the 4-triazolyl substituents. Epub 2017 Aug 1. Benzylidene acetals are used as protecting groups in glycochemistry. Typically, alkyl derivatives resulted in effective gelation in … Copyright © 2018. Clipboard, Search History, and several other advanced features are temporarily unavailable. Discrete and Polymeric Self-Assembled Palladium(II) Complexes as Supramolecular Gelators. The general structure and gelation trend obtained here can be useful in designing sugar based biomaterials. Naproxen was used as a model drug and it formed co-gels with compound 25 in DMSO water mixtures. Find NCBI SARS-CoV-2 literature, sequence, and clinical content: https://www.ncbi.nlm.nih.gov/sars-cov-2/. We expect that further structural optimization can lead to more effective gelators that are compatible with different drug molecules for encapsulation and sustained release. Synthesis and Study of Molecular Assemblies Formed by 4,6-O-(2-Phenylethylidene)-Functionalized d-Glucosamine Derivatives. This site needs JavaScript to work properly.