220073-77-8Relevant articles and documents
Structure, activity and stereoselectivity of NADPH-dependent oxidoreductases catalysing the S-selective reduction of the imine substrate 2-methylpyrroline
Man, Henry,Wells, Elizabeth,Hussain, Shahed,Leipold, Friedemann,Hart, Sam,Turkenburg, Johan P.,Turner, Nicholas J.,Grogan, Gideon
, p. 1052 - 1059 (2015/05/05)
Oxidoreductases from Streptomyces sp. GF3546 [3546-IRED], Bacillus cereus BAG3X2 (BcIRED) and Nocardiopsis halophila (NhIRED) each reduce prochiral 2-methylpyrroline (2MPN) to (S)-2-methylpyrrolidine with >95 % ee and also a number of other imine substrates with good selectivity. Structures of BcIRED and NhIRED have helped to identify conserved active site residues within this subgroup of imine reductases that have S selectivity towards 2MPN, including a tyrosine residue that has a possible role in catalysis and superimposes with an aspartate in related enzymes that display R selectivity towards the same substrate. Mutation of this tyrosine residue - Tyr169 - in 3546-IRED to Phe resulted in a mutant of negligible activity. The data together provide structural evidence for the location and significance of the Tyr residue in this group of imine reductases, and permit a comparison of the active sites of enzymes that reduce 2MPN with either R or S selectivity.
Kinetic resolution of propargylamines via a highly enantioselective non-enzymatic N-acylation process
Kolleth, Amandine,Christoph, Sarah,Arseniyadis, Stellios,Cossy, Janine
, p. 10511 - 10513,3 (2020/09/02)
The non-enzymatic kinetic resolution of diversely substituted primary propargylic amines is reported featuring a highly selective acetyl transfer using (1S,2S)-1 in conjunction with AliquatTM 336, affording the corresponding enantio-enriched N-
Asymmetric syntheses of N-acetyl-(R)-coniine and N-Boc-(2R,6R)-solenopsin A via ring-closing metathesis
Kumareswaran, Ramaiah,Hassner, Alfred
, p. 2269 - 2276 (2007/10/03)
Asymmetric syntheses of piperidine alkaloids N-acetyl-(R)-coniine and (2R,6R)-trans-solenopsin were achieved utilizing stereoselective additions of allylphenylsulfone to chiral alkyl-N-sulfinylimines and ring-closing olefin metathesis.