918409-09-3Relevant academic research and scientific papers
Rational Design and Synthesis of Selective PRMT4 Inhibitors: A New Chemotype for Development of Cancer Therapeutics**
Sutherland, Mathew,Li, Alice,Kaghad, Anissa,Panagopoulos, Dimitrios,Li, Fengling,Szewczyk, Magdalena,Smil, David,Scholten, Cora,Bouché, Léa,Stellfeld, Timo,Arrowsmith, Cheryl H.,Barsyte, Dalia,Vedadi, Masoud,Hartung, Ingo V.,Steuber, Holger,Britton, Robert,Santhakumar, Vijayaratnam
supporting information, p. 1116 - 1125 (2021/03/08)
Protein arginine N-methyl transferase 4 (PRMT4) asymmetrically dimethylates the arginine residues of histone H3 and nonhistone proteins. The overexpression of PRMT4 in several cancers has stimulated interest in the discovery of inhibitors as biological tools and, potentially, therapeutics. Although several PRMT4 inhibitors have been reported, most display poor selectivity against other members of the PRMT family of methyl transferases. Herein, we report the structure-based design of a new class of alanine-containing 3-arylindoles as potent and selective PRMT4 inhibitors, and describe key structure–activity relationships for this class of compounds.
Synthesis and use of N-Fmoc-l-fluoroalanine
Carpentier, Claudia,Godbout, Rapha?l,Otis, Fran?ois,Voyer, Normand
supporting information, p. 1244 - 1246 (2015/03/04)
We report a practical synthesis of N-Fmoc protected l-fluoroalanine 6 from l-serine. The key step involves a deoxofluorination reaction which was best achieved using XtalFluor-E in the presence of triethylamine trihydrofluoride. We also report the use of 6 in solid-phase peptide synthesis for the preparation of a model tripeptide demonstrating the possibility of incorporating a fluorinated probe in a peptide without elimination. Furthermore, cleavage of the dipeptide permitted to verify that 6 has a high enantiopurity.
(2R)- and (2S)-3-fluoroalanine and their N-methyl derivatives: Synthesis and incorporation in peptide scaffolds
Hoveyda, Hamid R.,Pinault, Jean-Francois
, p. 5849 - 5852 (2007/10/03)
(Diagram presented) A convergent synthetic methodology has been developed to access both (2S)- and (2R)-3-fluoroalanine and their corresponding N-methyl analogues, in optically pure form, through a common oxazolidinone intermediate that can be obtained fr
