75703-25-2Relevant academic research and scientific papers
Engineering bromodomains with a photoactive amino acid by engaging 'Privileged' tRNA synthetases
Wagner, Shana,Sudhamalla, Babu,Mannes, Philip,Sappa, Sushma,Kavoosi, Sam,Dey, Debasis,Wang, Sinan,Islam, Kabirul
, p. 3641 - 3644 (2020/04/07)
Site-specific placement of unnatural amino acids, particularly those responsive to light, offers an elegant approach to control protein function and capture their fleeting 'interactome'. Herein, we have resurrected 4-(trifluoromethyldiazirinyl)-phenylalan
Rapid Mapping of Protein Interactions Using Tag-Transfer Photocrosslinkers
Horne, Jim E.,Walko, Martin,Calabrese, Antonio N.,Levenstein, Mark A.,Brockwell, David J.,Kapur, Nikil,Wilson, Andrew J.,Radford, Sheena E.
, p. 16688 - 16692 (2018/11/27)
Analysing protein complexes by chemical crosslinking-mass spectrometry (XL-MS) is limited by the side-chain reactivities and sizes of available crosslinkers, their slow reaction rates, and difficulties in crosslink enrichment, especially for rare, transie
Ginkgolide derivatives for photolabeling studies: Preparation and pharmacological evaluation
Str?mgaard, Kristian,Saito, D. Roland,Shindou, Hideo,Ishii, Satoshi,Shimizu, Takao,Nakanishi, Koji
, p. 4038 - 4046 (2007/10/03)
The terpene trilactones (TTLs), ginkgolides and bilobalide, are structurally unique constituents of Ginkgo biloba extracts, which exhibit various neuromodulatory properties. Although the TTLs are believed to be responsible for some of these effects, the s
4-(1-Azi-2,2,2-trifluoroethyl)benzoic Acid, a Highly Photolabile Carbene Generating Label Readily Fixable to Biochemical Agents
Nassal, Michael
, p. 1510 - 1523 (2007/10/02)
The title compound is synthesized starting from either 4-bromobenzyl tert butyldimethylsilyl ether (5b) or 4-bromobenzyl tert-butyl ether (5c) or - most simply - from 4-bromotoluene (5a).In the first step Br was replaced by Li using n-butyllithium, then the organometallic compounds were converted into the respective trifluoroacetophenones 6a - c with N-trifluoroacetylpiperidine.The azi moiety (diazirine) was prepared from the oximes 7a - c via O-tosyloximes 8a - c plus ammonia yielding the diaziridines 9a - c and oxidation of the latter with Ag2O.Oxidation by permanganate - of the ethers after acidic cleavage - yields the title compound 12.On irradation (λ > 300 nm) 12 by elimination of N2 with a half-life period of 22 s generates the corresponding carbene.At the same time from 12 with ca. 20percent the yellow isomeric 4-(1-diazo-2,2,2-trifluoroethyl)benzoic acid (20) is formed which is photolyzed generating the same carbene as 12.The synthesis of 20 is described starting from 4-bromobenzaldehyde. - The diazirine 12 as its N-hydroxysuccinimide ester 13, or using other methods of amide synthesis, can readily be coupled to amino functions of biochemically interesting agents thus forming photoaffinity labels.
