81216-14-0Relevant academic research and scientific papers
EPIGENETIC PROFILING METHOD
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Page/Page column 17; 18; 19, (2021/04/01)
A method for analyzing DNA comprises forming labelled DNA fragments by cleaving genomic DNA into DNA fragments, selectively functionalizing any non-methylated CpG sites present in the DNA with a linker comprising a hydrolysable moiety, and attaching a label to the linker. The method further comprises separating the labelled DNA fragments from any non-labelled DNA fragments, hydrolysing the hydrolysable moiety of the linker of the separated labelled DNA fragments so as to release the DNA fragments from the label, and sequencing the released DNA fragments.
Catalytic Access to Functionalized Allylic gem-Difluorides via Fluorinative Meyer–Schuster-Like Rearrangement
An, Rui,Li, Huimin,Liao, Lihao,Wu, Jin-Ji,Xu, Yang,Zhao, Xiaodan
supporting information, p. 11010 - 11019 (2020/05/18)
An unprecedented approach for efficient synthesis of functionalized allylic gem-difluorides via catalytic fluorinative Meyer–Schuster-like rearrangement is disclosed. This transformation proceeded with readily accessible propargylic fluorides, and low-cost B–F reagents and electrophilic reagents by sulfide catalysis. A series of iodinated, brominated, and trifluoromethylthiolated allylic gem-difluorides that were difficult to access by other methods were facilely produced with a wide range of functional groups. Importantly, the obtained iodinated products could be incorporated into different drugs and natural products, and could be expediently converted into many other valuable gem-difluoroalkyl molecules as well. Mechanistic studies revealed that this reaction went through a regioselective fluorination of alkynes followed by a formal 1,3-fluorine migration under the assistance of the B–F reagents to give the desired products.
Hydroaminoalkylation of Allenes
Bielefeld, Jens,Mannhaupt, Steffen,Schmidtmann, Marc,Doye, Sven
supporting information, p. 967 - 971 (2019/05/10)
The first examples of early-transition-metal-catalyzed hydroaminoalkylation reactions of allenes are reported. Initial studies performed with secondary aminoallenes led to the identification of a suitable titanium catalyst and revealed that under the reaction conditions, the initially formed hydroaminoalkylation products undergo an unexpected titanium-catalyzed rearrangement to form the thermodynamically more stable allylamines. The assumption that this rearrangement involves a reactive allylic cation intermediate provides a simple explanation of the fact that no successful early-transition-metal-catalyzed hydroaminoalkylations of allenes have previously been reported. As a result of the generation of the corresponding cation, the titanium-catalyzed intermolecular hydroaminoalkylation of propa-1,2-diene unexpectedly gives an aminocyclopentane product formed by incorporation of two equivalents of propa-1,2-diene.
Enzyme-like Click Catalysis by a Copper-Containing Single-Chain Nanoparticle
Chen, Junfeng,Wang, Jiang,Bai, Yugang,Li, Ke,Garcia, Edzna S.,Ferguson, Andrew L.,Zimmerman, Steven C.
supporting information, p. 13695 - 13702 (2018/10/02)
A major challenge in performing reactions in biological systems is the requirement for low substrate concentrations, often in the micromolar range. We report that copper cross-linked single-chain nanoparticles (SCNPs) are able to significantly increase the efficiency of copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) reactions at low substrate concentration in aqueous buffer by promoting substrate binding. Using a fluorogenic click reaction and dye uptake experiments, a structure-activity study is performed with SCNPs of different size and copper content and substrates of varying charge and hydrophobicity. The high catalytic efficiency and selectivity are attributed to a mechanism that involves an enzyme-like substrate binding process. Saturation-transfer difference (STD) NMR spectroscopy, 2D-NOESY NMR, kinetic analyses with varying substrate concentrations, and computational simulations are consistent with a Michaelis-Menten, two-substrate, random-sequential enzyme-like kinetic profile. This general approach may prove useful for developing more-sustainable catalysts and agents for biomedicine and chemical biology.
Discovery of a Highly Selective Cell-Active Inhibitor of the Histone Lysine Demethylases KDM2/7
Gerken, Philip A.,Wolstenhulme, Jamie R.,Tumber, Anthony,Hatch, Stephanie B.,Zhang, Yijia,Müller, Susanne,Chandler, Shane A.,Mair, Barbara,Li, Fengling,Nijman, Sebastian M. B.,Konietzny, Rebecca,Szommer, Tamas,Yapp, Clarence,Fedorov, Oleg,Benesch, Justin L. P.,Vedadi, Masoud,Kessler, Benedikt M.,Kawamura, Akane,Brennan, Paul E.,Smith, Martin D.
supporting information, p. 15555 - 15559 (2017/12/02)
Histone lysine demethylases (KDMs) are of critical importance in the epigenetic regulation of gene expression, yet there are few selective, cell-permeable inhibitors or suitable tool compounds for these enzymes. We describe the discovery of a new class of inhibitor that is highly potent towards the histone lysine demethylases KDM2A/7A. A modular synthetic approach was used to explore the chemical space and accelerate the investigation of key structure–activity relationships, leading to the development of a small molecule with around 75-fold selectivity towards KDM2A/7A versus other KDMs, as well as cellular activity at low micromolar concentrations.
Enantiomerically enriched tris(boronates): Readily accessible conjunctive reagents for asymmetric synthesis
Coombs, John R.,Zhang, Liang,Morken, James P.
supporting information, p. 16140 - 16143 (2015/01/09)
The catalytic enantioselective diboration of vinyl boronate esters furnishes chiral tris(boronates) in a selective fashion. Subsequent deborylative alkylation occurs in a diastereoselective fashion, both for intermolecular and intramolecular processes.
Identification of α2 macroglobulin as a major serum ghrelin esterase
Eubanks, Lisa M.,Stowe, G. Neil,De Lamo Marin, Sandra,Mayorov, Alexander V.,Hixon, Mark S.,Janda, Kim D.
supporting information; experimental part, p. 10699 - 10702 (2012/01/04)
Fishing for a protein: An analogue of the appetite-stimulating hormone ghrelin containing a phosphonofluoridate moiety and a terminal alkyne functions as a probe to capture the protein α2 macroglobulin (red; see picture). The extraction of the
