Related Experiment Video
Updated: Feb 3, 2026
07:24
Visible-light Induced Reduction of Graphene Oxide Using Plasmonic Nanoparticle
Published on: September 22, 2015
14.9K
Development of a Visible Light Triggerable Traceless Staudinger Ligation Reagent.
Peng Hu1, Karsten Berning1, Yun-Wah Lam1
1Department of Chemistry , City University of Hong Kong , Hong Kong SAR , China.
The Journal of Organic Chemistry
|October 26, 2018
Summary
New anthracene photocages enable visible light-triggered traceless Staudinger ligation for bioconjugation. The best performing photocage allows for fast photo-uncaging and efficient synthesis of oligopeptides.
Area of Science:
- Organic Chemistry
- Photochemistry
- Bioconjugation Chemistry
Background:
- Development of photocages for controlled release of chemical species.
- Need for visible light-responsive photocages for biological applications.
- Advancements in Staudinger ligation for bioconjugation.
Purpose of the Study:
- Synthesize novel 9-methylenylanthracene photocages for diphenylphosphinothioesters.
- Investigate their photo-uncaging properties using visible light.
- Optimize photocage performance for efficient bioconjugation.
Main Methods:
- Synthesis of substituted 9-methylenylanthracene derivatives.
- Photochemical studies to determine uncaging efficiency and wavelength response.
- Application in visible-light-induced traceless Staudinger ligation for oligopeptide synthesis.
Main Results:
- Several novel photocages were synthesized, with (10-(3,3-dimethylbut-1-yn-1-yl)anthracen-9-yl)methyl showing superior performance.
- This photocage exhibits fast photo-uncaging and minimal byproduct formation under visible light.
- Demonstrated efficient visible-light-triggered synthesis of oligopeptides with yields of 31-43%.
Conclusions:
- The developed photocages are effective for visible light-triggered traceless Staudinger ligation.
- This methodology enables in situ synthesis of functional peptides and proteins.
- Potential applications in regulating cellular functions via photoclick chemistry.
Related Concept Videos
01:26EDTA: Auxiliary Complexing Reagents
1.4K
EDTA titrations are usually carried out in highly basic conditions, where the fully deprotonated form of EDTA, Y4−, actively complexes with the free metal ions in the solution. Several metal ions precipitate as hydrous oxide (hydroxides, oxides, or oxyhydroxides) under these conditions, lowering the concentration of free metal ions in the solution. For this reason, auxiliary complexing agents or ligands such as ammonia, tartrate, citrate, or triethanolamine are used in EDTA titrations to...
1.4K
01:35Light as Energy
95.9K
The energy required to carry out photosynthesis is light— typically electromagnetic radiation from the sun. The range of all possible wavelengths is known as the electromagnetic spectrum.
Photons
A photon is a discrete electromagnetic particle or bundle of energy. Photons are characterized by their frequency, wavelength, and amplitude, similar to the properties of a wave. Waves with higher frequencies transmit more energy and have shorter wavelengths than longer wavelengths that transmit...
Photons
A photon is a discrete electromagnetic particle or bundle of energy. Photons are characterized by their frequency, wavelength, and amplitude, similar to the properties of a wave. Waves with higher frequencies transmit more energy and have shorter wavelengths than longer wavelengths that transmit...
95.9K
01:14Acid Halides to Ketones: Gilman Reagent
4.1K
Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen...
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen...
4.1K
02:00Photoreceptors and Plant Responses to Light
28.5K
Light plays a significant role in regulating the growth and development of plants. In addition to providing energy for photosynthesis, light provides other important cues to regulate a range of developmental and physiological responses in plants.
28.5K
02:12The Wave Nature of Light
61.3K
The nature of light has been a subject of inquiry since antiquity. In the seventeenth century, Isaac Newton performed experiments with lenses and prisms and was able to demonstrate that white light consists of the individual colors of the rainbow combined together. Newton explained his optics findings in terms of a "corpuscular" view of light, in which light was composed of streams of extremely tiny particles traveling at high speeds according to Newton's laws of motion.
61.3K
02:16Light Acquisition
9.6K
In order to produce glucose, plants need to capture sufficient light energy. Many modern plants have evolved leaves specialized for light acquisition. Leaves can be only millimeters in width or tens of meters wide, depending on the environment. Due to competition for sunlight, evolution has driven the evolution of increasingly larger leaves and taller plants, to avoid shading by their neighbors with contaminant elaboration of root architecture and mechanisms to transport water and nutrients.
9.6K