5694-68-8Relevant articles and documents
Control of RNA with quinone methide reversible acylating reagents
Jash, Biswarup,Jun, Yong Woong,Kool, Eric T.,Park, Hyun Shin,Xiao, Lu
supporting information, p. 8367 - 8376 (2021/10/12)
Caging RNA by polyacylation (cloaking) has been developed recently as a simple and rapid method to control the function of RNAs. Previous approaches for chemical reversal of acylation (uncloaking) made use of azide reduction followed by amine cyclization, requiring ~2-4 h for the completion of cyclization. In new studies aimed at improving reversal rates and yields, we have designed novel acylating reagents that utilize quinone methide (QM) elimination for reversal. The QM de-acylation reactions were tested with two bioorthogonally cleavable motifs, azide and vinyl ether, and their acylation and reversal efficiencies were assessed with NMR and mass spectrometry on model small-molecule substrates as well as on RNAs. Successful reversal both with phosphines and strained alkenes was documented. Among the compounds tested, the azido-QM compoundA-3displayed excellent de-acylation efficiency, witht1/2for de-acylation of less than an hour using a phosphine trigger. To test its function in RNA caging,A-3was successfully applied to control EGFP mRNA translationin vitroand in HeLa cells. We expect that this molecular caging strategy can serve as a valuable tool for biological investigation and control of RNAs bothin vitroand in cells.
PROCESS FOR THE MANUFACTURE OF FLUOROSURFACTANTS
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Page/Page column 12, (2010/04/03)
This invention pertains to a novel process for the manufacture of a perfluorooxycarboxylate of formula (I): RfO-CF2CF2-O-CF2-COOXa (I) wherein Rf is a perfluoro(oxy)alkyl group, and Xa is H, a monovalent metal or an ammonium group of formula NRN4, with RN, equal or different at each occurrence, being H or a C1-6 hydrocarbon group, said process comprising: (A) reacting a perfluorovinylether of formula Rf-O-CF=CF2 with an ethylene glycol derivative selected among ethylene glycol (HO-CH2CH2-OH), glycolic acid (HO-CH2-COOH), glycolaldheyde (HO-CH2-CHO) and protected derivatives thereof, so as to yield the corresponding addition product of formula Rf-O-CFH-CF2-O-CH2-E, with Rf having the same meaning as above detailed, and E being selected among -CH2OH, -COOH and -CHO; (B) optionally protecting functional group E with suitable chemistry; (C) fluorinating said (protected) addition product to yield the corresponding perfluorinated addition product; (D) optionally deprotecting said perfluorinated addition product to yield corresponding acyl fluoride of formula Rf-O-CF2-CF2-O-CF2-C(O)F; (E) hydrolyzing and, optionally, neutralizing, said acyl fluoride for yielding the perfluorooxycarboxylate of formula (I).
Liquid-phase Oxidation of 1,2-Ethane Diol
Schnurpfeil, D.,Maurer, G.
, p. 307 - 310 (2007/10/02)
The oxidation rate and the kind of oxidation products in the reaction of 1,2-ethane diol (1) with molecular oxygen in liquid phase at 150 deg C were investigated. 1 has a very low oxidation rate.Cu-, Zn-, Fe-, Co- and Al-acetylacetonates as catalysts increase the reaction rate.The main-products of the investigated reaction are the 1,3-dioxolan (2), the 2-methyl-1,3-dioxolan (3) and the 2-methylol-1,3-dioxolan (4).The formation of formic and acetic acids and of the 1,3-dioxolanes is proved by GC, DC and HPLC.