Monosaccharides as Versatile Units for Water-Soluble Supramolecular Polymers

Chemistry : a European Journal
Christianus M A LeendersE W Meijer

Abstract

We introduce monosaccharides as versatile water-soluble units to compatibilise supramolecular polymers based on the benzene-1,3,5-tricarboxamide (BTA) moiety with water. A library of monosaccharide-based BTAs is evaluated, varying the length of the alkyl chain (hexyl, octyl, decyl and dodecyl) separating the BTA and saccharide units, as well as the saccharide units (α-glucose, β-glucose, α-mannose and α-galactose). In all cases, the monosaccharides impart excellent water compatibility. The length of the alkyl chain is the determining factor to obtain either long, one-dimensional supramolecular polymers (dodecyl spacer), small aggregates (decyl spacer) or molecularly dissolved (octyl and hexyl) BTAs in water. For the BTAs comprising a dodecyl spacer, our results suggest that a cooperative self-assembly process is operative and that the introduction of different monosaccharides does not significantly change the self- assembly behaviour. Finally, we investigate the potential of post-assembly functionalisation of the formed supramolecular polymers by taking advantage of dynamic covalent bond formation between the monosaccharides and benzoxaboroles. We observe that the supramolecular polymers readily react with a fluorescent benzoxa...Continue Reading

References

Apr 28, 2005·Biosensors & Bioelectronics·John C PickupDavid J S Birch
Nov 17, 2005·Journal of the American Chemical Society·Byung-Sun KimMyongsoo Lee
Mar 30, 2006·Journal of the American Chemical Society·Meenakshi Dowlut, Dennis G Hall
Dec 29, 2006·Chemistry & Biodiversity·Valery M Dembitsky
Aug 7, 2007·Journal of the American Chemical Society·Jennifer N CambreBrent S Sumerlin
Mar 19, 2009·Angewandte Chemie·Marion K Müller, Luc Brunsveld
Sep 23, 2009·Chemical Reviews·Tom F A De GreefE W Meijer
Mar 18, 2010·Chemical Communications : Chem Comm·Akira MatsumotoYuji Miyahara
Nov 23, 2011·Journal of the American Chemical Society·Abhijeet P BapatBrent S Sumerlin
Feb 7, 2012·Journal of the American Chemical Society·Gregory A EllisRonald T Raines
Feb 22, 2012·Journal of the American Chemical Society·Hyunkyu KimKyoung Taek Kim
Nov 3, 2012·The Journal of Organic Chemistry·John W Tomsho, Stephen J Benkovic
Nov 20, 2012·Organic & Biomolecular Chemistry·Katja Petkau-Milroy, Luc Brunsveld
Feb 1, 2013·Chemical Communications : Chem Comm·Christianus M A LeendersE W Meijer
May 2, 2013·The Journal of Organic Chemistry·Mayte A Martínez-AguirreAnatoly K Yatsimirsky
Jul 10, 2013·Proceedings of the National Academy of Sciences of the United States of America·Lorenzo AlbertazziE W Meijer
Mar 29, 2014·Chemistry : a European Journal·George C FeastG Paul Savage
Jan 12, 2012·ACS Medicinal Chemistry Letters·John W TomshoStephen J Benkovic
Feb 24, 2015·Nature Communications·Matthew B BakerE W Meijer
Jun 18, 2015·Organic & Biomolecular Chemistry·Laura N NeumannE W Meijer

❮ Previous
Next ❯

Citations

Jun 15, 2016·Langmuir : the ACS Journal of Surfaces and Colloids·Soumik DindaPrasanta Kumar Das
Oct 5, 2016·Journal of the American Chemical Society·Matteo GarzoniGiovanni M Pavan
Aug 24, 2017·Chemistry : a European Journal·Soumik DindaPrasanta Kumar Das
Sep 19, 2018·Chemical Communications : Chem Comm·Sandra M C SchoenmakersAnja R A Palmans
Jan 31, 2019·Chemical Communications : Chem Comm·David VrbataPavel Matějíček
Aug 8, 2019·Journal of the American Chemical Society·Simone I S HendrikseE W Meijer
Sep 30, 2020·Biomacromolecules·Silvia Varela-AramburuE W Meijer
Oct 19, 2021·Biomacromolecules·Silvia Varela-AramburuE W Meijer

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.