4-Methyl-3-morpholinecarboxylic acid hydrochloride (1:1)
CAS Number:
1240518-90-4
Molecular Formula:
C6H12ClNO3
Light controlled reversible Michael addition of cysteine: a new tool for dynamic site-specific labeling of proteins
Literature Information
Publication Date
2023-01-25
DOI
10.1039/D2AN01395A
Impact Factor
4.616
Authors
Soham Maity, Courtney Bingham, Wei Sheng, Nona Ehyaei, Debarshi Chakraborty, Setare Tahmasebi-Nick, Thomas E. Kimmel, Chrysoula Vasileiou, James H. Geiger, Babak Borhan
View Original
Abstract
Cysteine-based Michael addition is a widely employed strategy for covalent conjugation of proteins, peptides, and drugs. The covalent reaction is irreversible in most cases, leading to a lack of control over the process. Utilizing spectroscopic analyses along with X-ray crystallographic studies, we demonstrate Michael addition of an engineered cysteine residue in human Cellular Retinol Binding Protein II (hCRBPII) with a coumarin analog that creates a non-fluorescent complex. UV-illumination reverses the conjugation, yielding a fluorescent species, presumably through a retro-Michael process. This series of events can be repeated between a bound and non-bound form of the cysteine reversibly, resulting in the ON–OFF control of fluorescence. The details of the mechanism of photoswitching was illuminated by recapitulation of the process in light irradiated single crystals, confirming the mechanism at atomic resolution.
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Source Journal
Analyst
CiteScore:
7.8
Self-citation Rate:
5.6%
Articles per Year:
653
Analyst publishes analytical and bioanalytical research that reports premier fundamental discoveries and inventions, and the applications of those discoveries, unconfined by traditional discipline barriers.
Recommended Compounds
![N-[2-(4-Hydroxyphenoxy)-4-nitrophenyl]methanesulfonamide structure](https://static.chemtradehub.com/structs/109/109032-22-6-7c88.webp "N-[2-(4-Hydroxyphenoxy)-4-nitrophenyl]methanesulfonamide structure")
N-[2-(4-Hydroxyphenoxy)-4-nitrophenyl]methanesulfonamide
CAS Number:
109032-22-6
Molecular Formula:
C13H12N2O6S
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