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Photoaffinity labeling and its application in structural biology

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Abstract

This review contains a brief consideration of some theoretical aspects of photoaffinity (photoreactive) labeling (PAL), and the most widely used photoreactive groups, such as arylazide, benzophenone, and 3-(trifluoromethyl)-3-phenyldiazirine, are characterized in comparison. Experimental methodology is described, including modern approaches of mass spectrometry for analysis of cross-linking products between the photoreactive probes and biomolecules. Examples of PAL application in diverse fields of structural biology during the last five-ten years are presented. Potential drug targets, transport processes, stereochemistry of interaction of G-protein-coupled receptors with ligands, as well as structural changes in nicotinic acetylcholine receptor are considered. Applications of photoaffinity ganglioside and phospholipid probes for studying biological membranes and of nucleotide probes in investigations of replicative and transcriptional complexes, as well as photoaffinity glycoconjugates for detecting carbohydrate-binding proteins are covered. In combination with modern techniques of instrumental analysis and computer-aided modeling, PAL remains the most important approach in studies on the organization of biological systems.

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Abbreviations

Bp:

benzoylphenyl

Bpa:

p-benzoylphenylalanine

CRF:

corticotropin-releasing factor

DAT:

dopamine protein transporter

Dcp:

diazocyclopentadien-2-ylcarbonyl

ESI:

electrospray ionization

GPCR:

G-protein-coupled receptor

GSph:

gangliosides

ILBP:

ileal lipid-binding protein

LC/MS:

liquid chromatography/mass spectrometry

MALDI:

matrix assisted laser desorption ionization

MDR:

multiple drug resistance

MS:

mass spectrometry

MS/MS:

tandem mass spectrometry

nAChR:

nicotinic acetylcholine receptor

Nab:

2-nitro-5-azidobenzoyl

Nap:

2-nitro-4-azidophenyl

PAL:

photoaffinity labeling

PC:

phosphatidylcholine

SE:

squalene epoxidase

TD:

transmembrane domain

Tfd:

3-(trifluoromethyl)-3-phenyldiazirine

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  1. Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, ul. Miklukho-Maklaya 16/10, 117997, Moscow, Russia

    E. L. Vodovozova

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Original Russian Text © E. L. Vodovozova, 2007, published in Biokhimiya, 2007, Vol. 72, No. 1, pp. 5–26.

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Vodovozova, E.L. Photoaffinity labeling and its application in structural biology. Biochemistry (Moscow) 72, 1–20 (2007). https://doi.org/10.1134/S0006297907010014

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