Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
Covalent Functionalization of Buckminsterfullerene with Perfluorophenyl Azide by Microwave Irradiation, Photochemical or Thermal Activation
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.ORCID iD: 0000-0003-1121-4007
(English)Manuscript (preprint) (Other academic)
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-173004OAI: oai:DiVA.org:kth-173004DiVA: diva2:851589
Note

QS 2015

Available from: 2015-09-07 Created: 2015-09-07 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.
Series
TRITA-CHE-Report, ISSN 1654-1081 ; 2015:33
Keyword
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
Identifiers
urn:nbn:se:kth:diva-172990 (URN)
Public defence
2015-09-28, F3, Lindstedtsvägen 26, KTH, Stockholm, 10:00 (English)
Opponent
Supervisors
Note

QC 20150907

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

Open Access in DiVA

No full text

Search in DiVA

By author/editor
Kong, NaRamström, OlofYan, Mingdi
By organisation
Organic Chemistry
Organic Chemistry

Search outside of DiVA

GoogleGoogle Scholar

urn-nbn

Altmetric score

urn-nbn
Total: 61 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf