Abstract
Background: Formation of Self-assembled monolayers (SAMs) is one of the most widely used methods to modify a surface to achieve the desired property. It is a very unique, yet simple method to produce highly ordered and stable monolayer on the surface. Adsorption of alkyl thiol to gold or other metal surface is one of the most commonly used methods for the SAM preparation. Biotin is a small molecule used extensively for labeling in biochemical research including bio-assays and biosensors, due to its strong affinity to proteins avidin (Ka~1015M-1) and streptavidin (Ka~1013M-1). Objective: Biotin-functionalized-PEG-PE-thiol linker is particularly useful for these studies carried out on surfaces. Current methods to synthesize biotinylated PEG-alkyl thiol linker are tedious because of the different reactive intermediate compounds involved in the process. We wanted to develop an alternative high-yielding synthetic route for the synthesis. Results: Here we report a scheme with improved yield for the synthesis of biotinylated PEG-alkyl thiol using the Traceless Staudinger Ligation. The synthesis can be carried out in large scale, making the process beneficial for industrial purposes. In-situ deprotection of the acetylated thiol allows simultaneous adsorption on a gold surface, resulting in stable, coordinated biotinylated monolayer. Monolayer formation was characterized by Fourier transform infrared spectroscopy (FTIR), contact angle and thickness measurement.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 411-415 |
| Number of pages | 5 |
| Journal | Current Organic Chemistry |
| Volume | 22 |
| Issue number | 4 |
| DOIs | |
| State | Published - Jan 1 2018 |
| Externally published | Yes |
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Keywords
- Biotinylation
- Self-assembled monolayers (SAM)
- Surface characterization
- Surface modification
- Thiol-gold attachment
- Traceless staudinger ligation
ASJC Scopus subject areas
- Organic Chemistry
Cite this
Traceless staudinger ligation for biotinylation of acetylated thiol-azido heterobifunctional linker and its attachment to gold surface. / Senapati, Subhadip; Biswas, Sudipta; Zhang, Peiming.
In: Current Organic Chemistry, Vol. 22, No. 4, 01.01.2018, p. 411-415.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Traceless staudinger ligation for biotinylation of acetylated thiol-azido heterobifunctional linker and its attachment to gold surface
AU - Senapati, Subhadip
AU - Biswas, Sudipta
AU - Zhang, Peiming
PY - 2018/1/1
Y1 - 2018/1/1
N2 - Background: Formation of Self-assembled monolayers (SAMs) is one of the most widely used methods to modify a surface to achieve the desired property. It is a very unique, yet simple method to produce highly ordered and stable monolayer on the surface. Adsorption of alkyl thiol to gold or other metal surface is one of the most commonly used methods for the SAM preparation. Biotin is a small molecule used extensively for labeling in biochemical research including bio-assays and biosensors, due to its strong affinity to proteins avidin (Ka~1015M-1) and streptavidin (Ka~1013M-1). Objective: Biotin-functionalized-PEG-PE-thiol linker is particularly useful for these studies carried out on surfaces. Current methods to synthesize biotinylated PEG-alkyl thiol linker are tedious because of the different reactive intermediate compounds involved in the process. We wanted to develop an alternative high-yielding synthetic route for the synthesis. Results: Here we report a scheme with improved yield for the synthesis of biotinylated PEG-alkyl thiol using the Traceless Staudinger Ligation. The synthesis can be carried out in large scale, making the process beneficial for industrial purposes. In-situ deprotection of the acetylated thiol allows simultaneous adsorption on a gold surface, resulting in stable, coordinated biotinylated monolayer. Monolayer formation was characterized by Fourier transform infrared spectroscopy (FTIR), contact angle and thickness measurement.
AB - Background: Formation of Self-assembled monolayers (SAMs) is one of the most widely used methods to modify a surface to achieve the desired property. It is a very unique, yet simple method to produce highly ordered and stable monolayer on the surface. Adsorption of alkyl thiol to gold or other metal surface is one of the most commonly used methods for the SAM preparation. Biotin is a small molecule used extensively for labeling in biochemical research including bio-assays and biosensors, due to its strong affinity to proteins avidin (Ka~1015M-1) and streptavidin (Ka~1013M-1). Objective: Biotin-functionalized-PEG-PE-thiol linker is particularly useful for these studies carried out on surfaces. Current methods to synthesize biotinylated PEG-alkyl thiol linker are tedious because of the different reactive intermediate compounds involved in the process. We wanted to develop an alternative high-yielding synthetic route for the synthesis. Results: Here we report a scheme with improved yield for the synthesis of biotinylated PEG-alkyl thiol using the Traceless Staudinger Ligation. The synthesis can be carried out in large scale, making the process beneficial for industrial purposes. In-situ deprotection of the acetylated thiol allows simultaneous adsorption on a gold surface, resulting in stable, coordinated biotinylated monolayer. Monolayer formation was characterized by Fourier transform infrared spectroscopy (FTIR), contact angle and thickness measurement.
KW - Biotinylation
KW - Self-assembled monolayers (SAM)
KW - Surface characterization
KW - Surface modification
KW - Thiol-gold attachment
KW - Traceless staudinger ligation
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U2 - 10.2174/1385272821666170830113054
DO - 10.2174/1385272821666170830113054
M3 - Article
VL - 22
SP - 411
EP - 415
JO - Current Organic Chemistry
JF - Current Organic Chemistry
SN - 1385-2728
IS - 4
ER -