Photochemistry of phenyl azide: chemical properties of the transient intermediates

Schrock, Alan K.; Schuster, Gary B.

doi:10.1021/ja00330a032

Cited by 153 publications

(118 citation statements)

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“…The aryl nitrene inserts into a number of different types of chemical bonds (12), making it possible to label any class of nucleic acid. Previously, aryl azide-containing agents such as PHOTOPROBE Biotin have been activated by irradiation with a mercury vapor bulb (7,11); however, to provide greater flexibility, we have developed protocols for activation with a handheld UV lamp ( λ = 366 nm, 115 V, 0.16 A) or heat. To demonstrate that labeling by heat and light are functionally equivalent, we labeled Hin dIII-digested λ DNA and oligonucleotides using heat and light (160-W mercury vapor bulb) activation and subsequently used these DNAs as Southern hybridization probes and PCR primers, respectively.…”

Section: Resultsmentioning

confidence: 99%

FastTag™ Nucleic Acid Labeling System: A Versatile Method for Incorporating Haptens, Fluorochromes and Affinity Ligands into DNA, RNA and Oligonucleotides

1998

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Section: Resultsmentioning

confidence: 99%

FastTag™ Nucleic Acid Labeling System: A Versatile Method for Incorporating Haptens, Fluorochromes and Affinity Ligands into DNA, RNA and Oligonucleotides

1998

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“…We also note that since extensive dialysis of the photolysed actin does not alter its behaviour low molecular weight decomposition products cannot account for the observed effects. The maximum efficiency of photo-crosslinking of the phenylazide group is about 30% (Schrock & Schuster, 1984). The result from urea-gel electrophoresis showed that modification of a specific lysine was about 65%.…”

Section: Discussionmentioning

confidence: 98%

Myosin filament ATPase is enhanced by intramolecularly cross-linked actin

Kwon

Hardwicke

Collins

et al. 1994

J Muscle Res Cell Motil

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Reaction of rabbit skeletal muscle F-actin with the lysine-directed photolabile cross-linker, N-5-azido-2-nitrobenzoyloxy succinimide was limited to Lysine-328 and Lysine-326, with Lysine-328 being labelled to a greater extent. Photolysis of the modified actin enhanced the actin-activated MgATPase activity of filamentous scallop myosin 3-4-fold more than unmodified actin, without affecting calcium sensitivity. Unphotolysed modified actin behaved as untreated actin, indicating that photolysis was essential for the effect. The actin-activated ATPase of filamentous rabbit myosin was similarly increased by photolysed N-5-azido-2-nitrobenzoyloxy succinimide-modified actin. After photolysis in either the monomeric (G-) or filamentous (F-) form, N-5-azido-2-nitrobenzoyloxy succinimide-modified actin moved as a monomeric (42 kDa) species on SDS gels, and depolymerized and polymerized readily, demonstrating that any cross-linking event produced by photolysis must be intramolecular. In contrast to the substantial increase in actin-activated ATPase activity observed when photolysed ANB-NOS-modified actin was added to filamentous myosin, the enhancement was not observed with the soluble HMM and S-1 fragments of myosin. Photolysed modified actin showed only poor movement on a rabbit HMM-coated surface in vitro motility assays. These results can be explained if the internally cross-linked G-actin subunits which comprise only a fraction of the actin population, either weaken the actin-actin contacts or have an increased affinity for myosin.

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“…162 -165 The high dilution of solutions of phenyl azide suppresses polymer formation and azobenzene forms instead. 166,167 This indicates that singlet intermediates ( 50 and/or 51 ) serve as a reservoir for triplet phenylnitrenes ( 3 52 ), which either undergo dimerization or react with azide 47 to give azobenzene. These reactions have never been directly monitored for 3 52 by time -resolved techniques.…”

Section: Photochemistry Of Phenyl Azidementioning

confidence: 99%