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Carbohydrate conjugation through microwave-assisted functionalization of single-walled carbon nanotubes using perfluorophenyl azides
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.ORCID iD: 0000-0001-7469-4197
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
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2015 (English)In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 405, 33-38 p.Article in journal (Refereed) Published
Abstract [en]

Carbohydrate-functionalized single-walled carbon nanotubes (SWNTs) were synthesized using microwave-assisted reaction of perfluorophenyl azide with the nanotubes. The results showed that microwave radiation provides a rapid and effective means to covalently attach carbohydrates to SWNTs, producing carbohydrate-SWNT conjugates for biorecognition. The carbohydrate-functionalized SWNTs were furthermore shown to interact specifically with cognate carbohydrate-specific proteins (lectins), resulting in predicted recognition patterns. The carbohydrate-presenting SWNTs constitute a new platform for sensitive protein-or cell recognition, which pave the way for glycoconjugated carbon nanomaterials in biorecognition applications.

Place, publisher, year, edition, pages
2015. Vol. 405, 33-38 p.
Keyword [en]
Single-walled carbon nanotubes, Microwave, Perfluorophenyl azide, Covalent functionalization, Carbohydrate, Lectin
National Category
Chemical Sciences
URN: urn:nbn:se:kth:diva-163964DOI: 10.1016/j.carres.2014.09.006ISI: 000350748400005PubMedID: 25746392ScopusID: 2-s2.0-84924200153OAI: diva2:809792

QC 20150505.

Correction in: Carbohydrate Research, Vol. 412, article number 6968, DOI: 10.1016/j.carres.2015.03.013, WOS: 000357542000012, Scopus: 2-s2.0-84934753187

Available from: 2015-05-05 Created: 2015-04-13 Last updated: 2015-09-07Bibliographically approved
In thesis
1. Carbohydrate-Functionalized Nanomaterials: Synthesis, Characterization and Biorecognition Studies
Open this publication in new window or tab >>Carbohydrate-Functionalized Nanomaterials: Synthesis, Characterization and Biorecognition Studies
2015 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis focuses on the development of carbohydrate coupling chemistry on nanomaterials and their biological activity studies. It is divided into two parts:

In part one, two carbohydrate immobilization approaches, based on perfluorophenyl azide (PFPA)-functionalized silica nanoparticles (SNPs), are presented, where the binding affinity of the glyconanoparticles was evaluated through carbohydrate-lectin interaction. In the first approach, PFPAfunctionalized SNPs were treated with propargylated glycosides and functionalized under copper-catalyzed azide-alkyne cycloaddition (CuAAC) conditions to give glyconanoparticles. For the second approach, a metal-free coupling chemistry based on perfluorophenyl azide-aldehyde-amine cycloaddition (AAAC) was developed for carbohydrate immobilization on PFPA-functionalized SNPs using glycosyl amine and phenylacetaldehyde. Subsequently, a quantitative fluorine nuclear magnetic resonance (19F qNMR) technique was developed to determine the carbohydrate density on the glyconanoparticles. The addition of an internal standard allowed the accurate determination of carbohydrate density, which was then used to calculate the apparent dissociation constant (Kd ) of the glyconanoparticles with lectin by a ligand competition assay. The developed approaches proved general and versatile, and the carbohydrate-presenting nanoplatforms showed high binding specificity in lectin binding.

In part two, microwave irradiation was used to functionalize carbon nanomaterials with PFPA followed by carbohydrate conjugation. The microwave-assisted method proved efficient for a number of carbon nanomaterials including carbon nanotubes (CNTs), graphene and fullerene. The carbohydrates on the glyconanomaterials retained their binding patterns towards cognate lectins.

Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2015. 69 p.
TRITA-CHE-Report, ISSN 1654-1081 ; 2015:33
carbohydrate, glyconanomaterials, perfluorophenyl azide (PFPA ), CuAAC, AAAC, coupling chemistry, 19 F q NMR, lectin, carbon nanomaterials, microwave irradiation
National Category
Chemical Sciences
Research subject
Chemistry; Biotechnology
urn:nbn:se:kth:diva-172990 (URN)
Public defence
2015-09-28, F3, Lindstedtsvägen 26, KTH, Stockholm, 10:00 (English)

QC 20150907

Available from: 2015-09-07 Created: 2015-09-04 Last updated: 2015-12-31Bibliographically approved

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Kong, NaShimpi, Manishkumar R.Ramström, OlofYan, Mingdi
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