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. 2011 Nov 4;50(45):10690-3.
doi: 10.1002/anie.201103759. Epub 2011 Sep 20.

Conjugate addition/cyclization sequence enables selective and simultaneous fluorescence detection of cysteine and homocysteine

Xiaofeng Yang  1 , Yixing Guo, Robert M Strongin
Affiliations

Conjugate addition/cyclization sequence enables selective and simultaneous fluorescence detection of cysteine and homocysteine

Xiaofeng Yang et al. Angew Chem Int Ed Engl. .
No abstract available

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Figures

Figure 1
Figure 1
Time-dependent fluorescence spectral changes of 4 [20 µm; EtOH/phosphate buffer (20 mm, pH 7.4, 2:8 v/v)] with 1 equiv of either a) Cys or c) Hcy. Time-dependent fluorescence intensity changes of 4 (20 µm) in the presence of 1 equiv of either b) Cys or d) Hcy; λex = 304 nm.
Figure 2
Figure 2
Fluorescence spectra of 4 [20 µm; EtOH/phosphate buffer (20 mm, pH 7.4; 2:8 v/v)] after 40 min in the presence of increasing concentrations of either a) Cys or b) Hcy; λex = 304 nm.
Figure 3
Figure 3
Time-dependent fluorescence intensity changes of 4 (10 µm) at λ = 487 nm upon adding either Cys or Hcy (both 20 µm) in CTAB media (1.0 mm) buffered at 7.4 (phosphate buffer, 20 mm). λex = 304 nm.
Figure 4
Figure 4
a) Fluorescence spectra of 4 (50 µm) and Cys (0–40 µm) in 10% deproteinized human plasma. b) Fluorescence spectra of 4 (50 µm) and Hcy (0–12 µm) in the presence of 40 µm Cys in 10% deproteinized human plasma. The plasma was diluted with EtOH/phosphate buffer (20 mm, pH 7.4; 2:8, v/v) and the reaction monitored at 40 min. λex = 330 nm. This data shows that physiologically relevant sensitivity and limits of detection, even upon sample dilution, can be obtained in detecting Cys and Hcy in blood plasma. Moreover, Hcy can be detected in the presence of excess Cys.
Scheme 1
Scheme 1
The formation of 3-carboxy-5-oxoperhydro-1,4-thiazepine (3a) from the condensation of acrylates (R = alkyl) and Cys.
Scheme 2
Scheme 2
The reaction sequence that enables the sensing of Cys and Hcy when using 4.
See this image and copyright information in PMC

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