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Structure of tert-butyl carbamate-terminated thiol chemisorbed to gold
Linköping University, Department of Physics, Chemistry and Biology. Linköping University, The Institute of Technology.
Linköping University, Department of Physics, Chemistry and Biology. Linköping University, The Institute of Technology.
2005 (English)In: Journal of Physical Chemistry B, ISSN 1520-6106, E-ISSN 1520-5207, Vol. 109, no 33, 16040-16046 p.Article in journal (Refereed) Published
Abstract [en]

Monolayers of tert-butyl carbamate-terminated thiol were formed by adsorption of the molecules onto polycrystalline gold substrate. The adsorbates were studied using techniques as X-ray photoelectron spectroscopy (XPS), near-edge X-ray absorption fine structure spectroscopy (NEXAFS), and infrared reflection−absorption spectroscopy (IRAS). The results provide the electronic structure, composition, characteristic fingerprint, and orientation of the molecular adsorbate. XPS verified that the thiolate group is chemically bonded to the gold surface and that a complete chemisorption of the molecule occurs. Elemental depth profiling by varying the excitation energy in XPS supports the angle-dependent XPS results. Both techniques showed that the tert-butyl group is oriented away from the gold surface. A nearly parallel orientation of the carbonyl group relative to the gold surface is deduced from the IRAS results. The main molecular axis is estimated to have an average tilt angle of about 38° relative to the gold surface normal on the basis of the NEXAFS results. Cyclic voltammetry indicates a less blocking capability of the adsorbates. Overall, the molecules are oriented in an upright manner with indications of presence of pinholes and/or defects possibly due to steric hindrance of the bulky tert-butyl group. This molecular system is envisioned to be of use for surface-based organic synthesis on gold substrates.

Place, publisher, year, edition, pages
2005. Vol. 109, no 33, 16040-16046 p.
National Category
Engineering and Technology
Identifiers
URN: urn:nbn:se:liu:diva-50436DOI: 10.1021/jp0526445OAI: oai:DiVA.org:liu-50436DiVA: diva2:271332
Available from: 2009-10-11 Created: 2009-10-11 Last updated: 2017-12-12
In thesis
1. Bioactive adsorbates on gold surfaces: structural properties and bio-interaction studies
Open this publication in new window or tab >>Bioactive adsorbates on gold surfaces: structural properties and bio-interaction studies
2005 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis investigates the properties of biomolecular, model adsorbates on gold such as amino acid derivatives, peptides and related organic molecules. Subsequent bin-interaction studies were also conducted. The physico-chemical and structural properties of the adsorbates were characterized using X-ray Photoelectron Spectroscopy (XPS), Infrared-Reflection Absmption Spectroscopy (IRAS) and Near-Edge X-ray Absmption Fine Structures spectroscopy (NEXAFS). Complementary techniques such as Null ellipsometry and Cyclic Voltammetry (CV) were also used. The interaction of the bioactive monolayers with biologically relevant molecules, such as proteins and metal ions, were investigated using Surface Plasmon Resonance (SPR) spectroscopy and Electrochendcallmpedance Spectroscopy (EIS).

The first part of the thesis is directed towards the interaction of bovine-brain G-protein with adsorbates involving arginine residues and receptor-derived peptides mimicking the 2nd and 3rd intracellular (ic) loop of the α2A Adrenergic G-protein coupledreceptor (GPCR). The general aim is to find a peptide sequence that will selectively, with high affinity, interact with the G-protein. The specific aims were to examine the importance of the presence of positively charged arginine residues, to investigate the influence of molecular orientation of the adsorbates, and to verify which intracellular loop has the highest affinity to the G-protein. The investigation involved characterizing the chemical composition and the molecular orientation of Arginine-based dipeptide adsorbates (Arg-Cys and Arg-Cysteandne) and receptor-detived peptides (GPR1R also labeled GPRi3c, GPR1K, GPR1A, GPRi2c, GPRi3n) innnobilized on gold surfaces, followed by G~protein interaction studies. On all the adsorbates subjected to interact with G-proteins, the presence of arginine residues was proven to be of special importance in the affinity of G-proteins. A molecularly"oriented Arg-Cysteamine, with main molecular axis perpendicular to the gold surface, showing more available arginines, attracts more G-proteins as compared to Arg-Cys that has a compact configuration when adsorbed on gold. The peptide adsorbates derived from the third ic loop (GPRi3c and GPRi3n) have higher affinity than peptides derived from the second ic loop (GPRi2c). This shows that this arginine-rich area of the third ic loop has a major influence on the affinity and selectivity of G-proteins.

Place, publisher, year, edition, pages
Linköping: Linköpings universitet, 2005. 76 p.
Series
Linköping Studies in Science and Technology. Dissertations, ISSN 0345-7524 ; 988
National Category
Natural Sciences
Identifiers
urn:nbn:se:liu:diva-30969 (URN)16648 (Local ID)91-8545-775-2 (ISBN)16648 (Archive number)16648 (OAI)
Public defence
2005-12-16, Hörsal Plank, Fysikhuset, Campus Valla, Linköping, 10:15 (Swedish)
Opponent
Available from: 2009-10-09 Created: 2009-10-09 Last updated: 2012-11-23

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Petoral, Rodrigo JrUvdal, Kajsa

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