4695-31-2Relevant articles and documents
Synthesis of a new disulfide Fmoc monomer for creating biologically susceptible linkages in peptide nucleic acid oligomers
Campbell, Brandon,Hood, Taylor,Shank, Nathaniel
, p. 394 - 398 (2019)
Peptide nucleic acids (PNA) are one of many synthetic mimics of DNA and RNA that have found applications as biological probes, as nano-scaffold components, and in diagnostics. In an effort to use PNA as constructs for cellular delivery we investigated the possibility of installing a biologically susceptible disulfide bond in the backbone of a PNA oligomer. Here we report the synthesis of a new abasic Fmoc monomer containing a disulfide bond that can be incorporated into a PNA oligomer (DS-PNA) using standard solid phase peptide synthesis. The disulfide bond survives cleavage from the resin and DS-PNA forms duplexes with complementary PNA oligomers. Initial studies aimed at determining if the disulfide bond is cleavable to reducing agents while in a duplex are explored using UV thermal analysis and HPLC.
Preparation method of 2-mercaptoisobutyric acid
-
Paragraph 0021; 0022, (2020/05/08)
The invention relates to a preparation method of 2-mercaptoisobutyric acid, which comprises the following steps: carrying out a reaction with methyl (ethyl) 2-bromoisobutyrate with thiourea to prepareisothiourea salt, and carrying out alkaline hydrolysis and acidification to obtain the 2-mercaptoisobutyric acid. The method has the advantages of low cost, mild reaction conditions and high yield, and is suitable for industrial production.
NitroxylFluor: A Thiol-Based Fluorescent Probe for Live-Cell Imaging of Nitroxyl
Pino, Nicholas W.,Davis, Jerome,Yu, Zhengxin,Chan, Jefferson
supporting information, p. 18476 - 18479 (2018/01/08)
Detection of nitroxyl (HNO), the transient one-electron reduced form of nitric oxide, is a significant challenge owing to its high reactivity with biological thiols (with rate constants as high as 109 M-1 s-1). To address this, we report a new thiol-based HNO-responsive trigger that can compete against reactive thiols for HNO. This process forms a common N-hydroxysulfenamide intermediate that cyclizes to release a masked fluorophore leading to fluorescence enhancement. To ensure that the cyclization step is rapid, our design capitalizes on two established physical organic phenomena; the alpha-effect and the Thorpe-Ingold effect. Using this new trigger, we developed NitroxylFluor, a selective HNO-responsive fluorescent probe. Treatment of NitroxylFluor with an HNO donor results in a 16-fold turn-on. This probe also exhibits excellent selectivity over various reactive nitrogen, oxygen, and sulfur species and efficacy in the presence of thiols (e.g., glutathione in mM concentrations). Lastly, we successfully performed live cell imaging of HNO using NitroxylFluor.