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Review
. 2010 May 12;110(5):2579-619.
doi: 10.1021/cr900301e.

Fluorescent analogs of biomolecular building blocks: design, properties, and applications

Renatus W Sinkeldam  1 , Nicholas J Greco, Yitzhak Tor
Affiliations
Review

Fluorescent analogs of biomolecular building blocks: design, properties, and applications

Renatus W Sinkeldam et al. Chem Rev. .
No abstract available

PubMed Disclaimer

Figures

Figure 2.1
Figure 2.1
A simplified Jablonski diagram.
Figure 2.2
Figure 2.2
Correlation of solvent polarity and Stokes shift of PRODAN.
Figure 3.1
Figure 3.1
Cyclization of the acyclic form of d-glucose shown in the open, pyranose, and furanose forms. Hemiacetal formation produces both the α and β anomers (i.e., C-1 epimers).
Figure 3.2
Figure 3.2
Structures of boronic acid–based saccharide sensors.
Figure 3.3
Figure 3.3
Labeling of reducing carbohydrates with amine–containing fluorophores.
Figure 3.4
Figure 3.4
ManLev, its expression on the cell-surface and subsequent acylhydrazone formation.
Figure 4.1
Figure 4.1
General structures of glycerophospholipids, sphingomyelin and examples of natural head groups.
Figure 4.2
Figure 4.2
Phospholipid architectures in aqueous media.
Figure 4.3
Figure 4.3
Non-covalent membrane probes that reside in the cell membrane interior.
Figure 4.4
Figure 4.4
Head–group labeled mamebrane probes.
Figure 4.5
Figure 4.5
Examples of ‘chain-end’ (4.13–4.21) and ‘on-chain’ (4.22) labeling.
Figure 4.6
Figure 4.6
Examples of ‘in-chain’ labeled chromophores.
Figure 4.7
Figure 4.7
Naturally occurring polyenes.
Figure 4.8
Figure 4.8
Structures of naturally occurring α-parinaric acid (4.31) and synthetic all trans-PnA (4.32), trans-PA (4.33), and all trans-PdA (4.34).
Figure 5.1
Figure 5.1
Fluorophores found in fluorescent proteins. Wildtype GFP (5.1) and the S65T point mutation EGFP (5.2), topaz (5.3), P4-3 (5.4), ECFP (5.5), and GdFP (5.6).
Figure 5.2
Figure 5.2
Naturally occurring fluorescent amino acids.
Figure 5.3
Figure 5.3
Tryptophan mimics.
Figure 5.4
Figure 5.4
Examples of amino acids containing heterocyclic chromophores.
Figure 5.5
Figure 5.5
Amino acids labeled with emissive heterocarbons.
Figure 5.6
Figure 5.6
Examples of dansyl decorated amino acids.
Figure 5.7
Figure 5.7
Polarity sensitive phthalimide analogs.
Figure 5.8
Figure 5.8
Photo–switchable probes 5.40 and 5.41.
Figure 6.1
Figure 6.1
The naturally occurring ribo- and deoxyribo-nucleosides. Note: in RNA, the bases A, T, G, C and U are connected to d-ribose at the 1’-position, where the sugar moiety in DNA is 2’-deoxy-d -ribose.
Figure 6.2
Figure 6.2
Selected examples of chromophoric base analogs, where R = 2′-deoxyribose.
Figure 6.3
Figure 6.3
Selected examples of pteridines (R = 2′-deoxyribose or ribose).
Figure 6.4
Figure 6.4
Examples of expanded nucleobase analogs (R= 2’-deoxyribose, 2’-OMe ribose or ribose and R2=3’,5’-O-TBDMS-2’-deoxyribose).
Figure 6.5
Figure 6.5
Expanded nucleobase analogs (R = 2′-deoxyribose).
Figure 6.6
Figure 6.6
Selected examples of extended base analogs (R1 = 2′-deoxyribose and R2 = 2′-deoxyuridine or 2′,3′-dideoxyuridine).
Figure 6.7
Figure 6.7
Examples of extended nucleobase analogs.
Figure 6.8
Figure 6.8
Examples of isomorphic nucleobase analogs, where R = 2′-deoxyribose or ribose.
Figure 6.9
Figure 6.9
Examples of isomorphic nucleobase analogs.
Figure 6.10
Figure 6.10
Common cycle for solid-phase assisted phosphoramidite oligonucleotide synthesis.
See this image and copyright information in PMC

References

    1. Sameiro M, Goncalves T. Chem. Rev. 2009;109:190. - PubMed
    1. Lakowicz JR. Principles of Fluorescence Spectroscopy. 3rd ed. New York: Springer; 2006.
    1. Bacia K, Schwille P. Methods. 2003;29:74. - PubMed
    1. Valeur B. Molecular Fluorescence, Principles and Applications. Weinheim: Wiley-VCH Verlag GmbH; 2002.
    1. Turro NJ. Modern Molecular Photochemistry of Organic Molecules. New York: University Science Books; 2009.

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