120465-56-7Relevant academic research and scientific papers
Cyclic acetals as cleavable linkers for affinity capture
Lee, Siyeon,Wang, Wei,Lee, Younjoo,Sampson, Nicole S.
, p. 8445 - 8452 (2015)
Labeling proteins with biotin is a widely used method to identify target proteins due to biotin's strong binding affinity for streptavidin. Combined with alkyne-azide cycloaddition, which enables the coupling of probes to targeted proteins, biotin tags linked to an alkyne or azide have become a powerful tool for purification and analysis of proteins in proteomics. However, biotin requires harsh elution conditions to release the captured protein from the bead matrix. Use of these conditions reduces signal to noise and complicates the analysis. To improve affinity capture, cleavable linkers have been introduced. Here, we demonstrate the use of a cyclic acetal biotin probe that is prepared easily from commercially available starting materials, is stable to cell lysates, yet is cleaved under mildly acidic conditions, and which provides an aldehyde for further elaboration of the protein, if desired.
Thiosemicarbazone Dynamic Combinatorial Chemistry: Equilibrator-Induced Dynamic State, Formation of Complex Libraries, and a Supramolecular On/Off Switch
Larsen, Dennis,Jeppesen, Anne,Kleinlein, Claudia,Pittelkow, Michael
, p. 8580 - 8589 (2017)
Dynamic combinatorial libraries that equilibrate under thermodynamic control and can be trapped kinetically when desired are key to creating complex systems that can mimic dynamic biological systems, such as the biochemical system of life. A much-sought-after feature is the ability to turn off the dynamic exchange of the system, in order to investigate a transient state away from thermodynamic equilibrium, and then turn on the dynamic exchange again. We describe here the first use of thiosemicarbazone exchange to form dynamic combinatorial libraries. The libraries were found to require a nucleophilic catalyst, or equilibrator, in order to reach thermodynamic equilibrium. This equilibrator approach adds a supramolecular level of control over the dynamic system and allows the dynamic exchange to be turned off by addition of 18-crown-6, which binds the equilibrator in a nonnucleophilic complex. The dynamic exchange can be restarted by addition of potassium ions that competitively bind 18-crown-6, thus liberating the equilibrator. The highly complex thiosemicarbazone-based macrocyclic libraries contain both [2]catenanes and sequence isomers, which can be distinguished by HPLC-MS/MS.
Haptens, antigens and antibodies of imatinib and N-demethylated imatinib and application thereof
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Paragraph 0035, (2021/06/09)
The invention relates to the technical field of immunological detection, and particularly discloses haptens, antigens and antibodies of imatinib and N-demethylated imatinib and application of the haptens, the antigens and the antibodies, the structure of
Graphitic carbon nitride catalysed photoacetalization of aldehydes/ketones under ambient conditions
Abdullah Khan,Teixeira, Ivo F.,Li, Molly M. J.,Koito, Yusuke,Tsang, Shik Chi Edman
supporting information, p. 2772 - 2775 (2016/02/18)
Graphitic-C3N4 is shown for the first time to catalyse photoacetalization of aldehydes/ketones with alcohols to acetals in high yields using visible light under ambient conditions; transient charge separation over the material is effective to catalyse the reaction in the absence of Lewis or Br?nsted acids, giving a new green alternative catalyst.
A General Access to Propargylic Ethers through Br?nsted Acid Catalyzed Alkynylation of Acetals and Ketals with Trifluoroborates
Baxter, Matthew,Bolshan, Yuri
supporting information, p. 13535 - 13538 (2015/09/22)
A general Br?nsted acid catalyzed methodology for the alkynylation of acetals and ketals with alkynyltrifluoroborate salts has been developed. The reaction proceeds rapidly to afford valuable synthetic building block propargylic ethers in good to excellent yields. Unlike Lewis acid catalyzed transformations of trifluoroborates, this approach does not proceed via unstable organodifluoroborane intermediate. As a result, the developed methodology features excellent functional group tolerance and good atom economy. Br?nsted acid catalyzed alkynylation of acetals and ketals is described. Alkynyltrifluoroborate salts react rapidly to afford propargylic ethers. Organodifluoroborane, which is a common intermediate in Lewis acid catalyzed reactions of trifluoroborates, has not been observed. The reaction exhibits generally high yields and excellent functional group tolerance.
A chaperonin as protein nanoreactor for atom-transfer radical polymerization
Renggli, Kasper,Nussbaumer, Martin G.,Urbani, Raphael,Pfohl, Thomas,Bruns, Nico
supporting information, p. 1443 - 1447 (2014/03/21)
The group II chaperonin thermosome (THS) from the archaea Thermoplasma acidophilum is reported as nanoreactor for atom-transfer radical polymerization (ATRP). A copper catalyst was entrapped into the THS to confine the polymerization into this protein cage. THS possesses pores that are wide enough to release polymers into solution. The nanoreactor favorably influenced the polymerization of Nisopropyl acrylamide and poly(ethylene glycol)methylether acrylate. Narrowly dispersed polymers with polydispersity indices (PDIs) down to 1.06 were obtained in the protein nanoreactor, while control reactions with a globular protein- catalyst conjugate only yielded polymers with PDIs above 1.84.
Highly efficient and chemoselective acetalization and thioacetalization of aldehydes catalyzed by propylphosphonic anhydride (T3P) at room temperature
Augustine, John Kallikat,Bombrun, Agnes,Sauer, Wolfgang H.B.,Vijaykumar, Pujari
, p. 5030 - 5033 (2012/11/07)
Propylphosphonic anhydride (T3P), a low toxic peptide coupling agent, has been demonstrated to be an efficient catalyst for the chemoselective acetalization and thioacetalization of aldehydes in the presence of ketones. Cyclic and acyclic acetals of diverse aldehydes were obtained in good to excellent yields at room temperature in the presence of a catalytic amount of T3P.
Endosomal pH-activatable magnetic nanoparticle-capped mesoporous silica for intracellular controlled release
Gan, Qi,Lu, Xunyu,Dong, Wenjie,Yuan, Yuan,Qian, Jiangchao,Li, Yongsheng,Shi, Jianlin,Liu, Changsheng
experimental part, p. 15960 - 15968 (2012/09/08)
Endosomal pH-driven linkage-disintegration is a promising strategy to achieve intracellular delivery and controlled drug release. In this paper, a rapid endosomal pH-sensitive MSNs ensemble (i.e., MCM-TAA-Fe3O 4) with magnetic nanopa
From static to dynamic: Escaping kinetic traps in hydrazone-based dynamic combinatorial libraries
Beeren, Sophie R.,Pittelkow, Michael,Sanders, Jeremy K. M.
supporting information; scheme or table, p. 7359 - 7361 (2011/08/06)
Thermodynamic control over kinetically-trapped mixtures of hydrazone-based macrocycles is achieved by addition of an aromatic monohydrazide to generate dynamic combinatorial libraries (DCLs) of linear and macrocyclic oligomers.
Single-step conversion of electron-deficient aldehydes into the corresponding esters in aqueous alcohols in the presence of iodine and sodium nitrite
Kiran,Ikeda, Reiko,Sakai, Norio,Konakahara, Takeo
experimental part, p. 276 - 282 (2010/03/26)
The direct conversion of aldehydes into their corresponding esters in the presence of iodine and sodium nitrite in aqueous alcohols is reported. In all these reactions, alcohol serves as reactant and also as reaction medium. Almost quantitative yields were obtained with aldehydes containing electron-withdrawing substituents and heterocyclic aldehydes. Georg Thieme Verlag Stuttgart.
