Syntheses of Nitro-Substituted Aryl Diazirines. An Entry to Chromogenic Carbene Precursors for Photoaffinity Labeling.

Hatanaka, Y.; Hashimoto, Makoto; Nakayama, Hitoshi; Kanaoka, Yuichi

doi:10.1248/cpb.42.826

Cited by 33 publications

(21 citation statements)

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“…(trifluoro-methyl)-3H-diazirin-3-yl]phenoxy}acetic acid (Hatanaka et al, 1994) in 1.8 ml of acetonitrile was added to a solution of 56.3 mg (8.2/xmol) of NT-II (obtained from Kemotex, Estonia) in 5 ml of 200 mM sodium phosphate buffer pH 8.0. The reaction mixture was stirred for 20 hr in the dark at room temperature.…”

Section: Preparation Of Nt-ii Nitrodiazirine Derivativesmentioning

confidence: 99%

Synthesis of nitrodiazirinyl derivatives of neurotoxin II fromNaja naja oxiana and their interaction with theTorpedo californica nicotinic acetylcholine receptor

et al. 1995

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Five singly modified nitrodiazirine derivatives of neurotoxin II (NT-II) from Naja naja oxiana were obtained after NT-II reaction with N-hydroxysuccinimide ester of (2-nitro-4-[3-(trifluoromethyl)-3H-diazirin-3yl]phenoxy)acet ic acid followed by chromatographic separation of the products. To localize the label positions, each derivative was first UV-irradiated and then subjected to reduction, carboxymethylation, and trypsinolysis. Tryptic digests were separated by reversed phase-HPLC, the labeled peptides being identified by mass spectrometry. The derivatives containing the photolabel at the position Lys 25, Lys 26, Lys 44, or Lys 46 were [125I]iodinated by the chloramine T procedure. Each iodinated derivative was found to form photoinduced cross-links with the membrane-bound nicotinic acetylcholine receptor (AChR) from Torpedo californica. The pattern of labeling the receptor's alpha, beta, gamma, or delta subunits was dependent on the photolabel position in the NT-II molecule and differed from that obtained earlier with an analogous series of p-azidobenzoyl derivatives of NT-II. The results obtained indicate that (i) different sides of the neurotoxin molecule are involved in the AChR binding, and (ii) fragments of the different AChR subunits are located close together at the neurotoxin-binding sites.

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Section: Preparation Of Nt-ii Nitrodiazirine Derivativesmentioning

confidence: 99%

Synthesis of nitrodiazirinyl derivatives of neurotoxin II fromNaja naja oxiana and their interaction with theTorpedo californica nicotinic acetylcholine receptor

et al. 1995

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“…To evaluate the properties of photoreactivity and exchangeability on Ns diazirine, a model compound bearing sulfonamide ethanol Ns diazirine 10 was synthesized. In designing Ns diazirine, we decided to install the trifluoromethyldiazirine moiety on the meta position of the nitro group so that the nitro group enhances photolysis and facilitates S N Ar reaction . Our synthesis began with the introduction of nitro group on 4‐chlorobenzaldehyde 1 via substitution aromatic nucleophilic reaction in the presence of potassium nitrate and sulfuric acid which gave us 86 % yield of nitro benzaldehyde 2 .…”

Section: Resultsmentioning

confidence: 99%

Design and Synthesis of Ligand‐Tag Exchangeable Photoaffinity Probe Utilizing Nosyl Chemistry

et al. 2019

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“…The key intermediate diazirine aldehyde 9 was prepared in seven steps starting from 3-bromoanisole ( 8 ) as described by the previous report for introduction of the 3-(trifluoromethyl)-diazirin-3-yl group [ 21 , 22 ]. The final oxidation of the aldehyde 9 to the acid 10 was performed using the combination of sodium chlorite with sulfamic acid in THF and water ( Scheme 3 ) [ 13 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis of a Dual-Labeled Probe of Dimethyl Lithospermate B with Photochemical and Fluorescent Properties

2011

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Dimethyl lithosermate B (DLB) is a highly potent natural antioxidant and antidiabetic polyphenol with unknown mode of action. To determine its cellular targets, a photochemical and fluorescent dimethyl lithopermate B probe was designed and efficiently synthesized. The dual-labeled chemical probe for biological application was evaluated by UV and fluorescence to determine its electrochemical absorption and emission properties. This probe could be valuable for investigating ligand-protein interactions and subcellular localization.

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Syntheses of Nitro-Substituted Aryl Diazirines. An Entry to Chromogenic Carbene Precursors for Photoaffinity Labeling.

Cited by 33 publications

References 1 publication

Synthesis of nitrodiazirinyl derivatives of neurotoxin II fromNaja naja oxiana and their interaction with theTorpedo californica nicotinic acetylcholine receptor

Synthesis of nitrodiazirinyl derivatives of neurotoxin II fromNaja naja oxiana and their interaction with theTorpedo californica nicotinic acetylcholine receptor

Design and Synthesis of Ligand‐Tag Exchangeable Photoaffinity Probe Utilizing Nosyl Chemistry

Synthesis of a Dual-Labeled Probe of Dimethyl Lithospermate B with Photochemical and Fluorescent Properties

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