Design and synthesis of a monofluoro-substituted aromatic amino acid as a conformationally restricted 19F NMR label for membrane-bound peptides
A monofluoro-substituted amino acid was designed to serve as a conformationally restricted label for solid-state 19F NMR distance measurements in membrane-bound peptides. The aromatic cis and trans isomers of 1-amino-3-(4-fluorophenyl)cyclobuta
Tkachenko, Anton N.,Mykhailiuk, Pavel K.,Radchenko, Dmytro S.,Babii, Oleg,Afonin, Sergii,Ulrich, Anne S.,Komarov, Igor V.
p. 3584 - 3591
(2014/06/23)
Enzymatic desymmetrization of prochiral 2-substituted-1,3-diamines: Preparation of valuable nitrogenated compounds
A wide range of prochiral 1, 3-diamines were first efficiently synthesized and subsequently desymmetrized by using lipase from Pseudomonas cepacia as catalyst and diallyl carbonate as alkoxycarbonylating agent. In all cases, the amino carbamates of R-configuration were recovered. Final selective cleavage of the N-allyloxycarbonyl moiety was carried out under mild reaction conditions, which demonstrates the high versatility and potential of this chemoenzymatic route as a source of intermediates in the synthesis of related optically active nitrogenated derivatives.
First desymmetrization of 1,3-propanediamine derivatives in organic solvent. Development of a new route for the preparation of optically active amines
The chemical synthesis and enzymatic desymmetrization of a panel of prochiral diamines have been successfully described for the first time using lipases in organic solvents. A family of 2-aryl-1,3-propanediamines has been obtained with high enantiopurity and good yields in the PSL-catalyzed reaction using diallyl carbonate in 1,4-dioxane.