Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 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

PubMed Disclaimer

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

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. Wood ZA, Schröder E, Harris JR, Poole LB. Trends Biochem. Sci. 2003;28:32–40. - PubMed
    2. Schulz J, Lindenau J, Seyfried J, Dichgans J. Eur. J. Biochem. 2000;267:4904–4911. - PubMed
    1. Wang XF, Cynader MS. J. Neurosci. 2001;21:3322–3331. - PMC - PubMed
    1. Shahrokhian S. Anal. Chem. 2001;73:5972–5978. - PubMed
    1. Refsum H, Ueland PM, Nygård O, Vollset SE. Annu. Rev. Med. 1998;49:31–62. - PubMed
    2. Seshadri S, Beiser A, Selhub J, Jacques PF, Rosenberg IH, D’Agostino RB, Wilson PWF, Wolf PA. N. Engl. J. Med. 2002;346:476–483. - PubMed
    3. Refsum H, Smith AD, Ueland PM, Nexo E, Clarke R, McPartlin J, Johnston C, Engbaek F, Schneede J, McPartlin C, Scott JM. Clin. Chem. 2004;50:3–32. - PubMed
    1. Huo F-J, Sun Y-Q, Su J, Chao J-B, Zhi H-J, Yin C-X. Org. Lett. 2009;11:4918–4921. - PubMed
    2. Zeng Y, Zhang GX, Zhang DQ. Anal. Chim. Acta. 2008;627:254–257. - PubMed

Publication types

LinkOut - more resources