113273-73-7Relevant academic research and scientific papers
Probing of the cis-5-phenyl proline scaffold as a platform for the synthesis of mechanism-based inhibitors of the Staphylococcus aureus sortase SrtA isoform
Kudryavtsev, Konstantin V.,Bentley, Matthew L.,McCafferty, Dewey G.
scheme or table, p. 2886 - 2893 (2009/09/05)
cis-5-Phenyl prolinates with electrophilic substituents at the fourth position of a pyrrolidine ring were synthesized by 1,3-dipolar cycloaddition of arylimino esters with divinyl sulfone and acrylonitrile. 4-Vinylsulfonyl 5-phenyl prolinates inhibit Staphylococcus aureus sortase SrtA irreversibly by modification of the enzyme Cys184 and could be used as hits for the development of antibacterials and antivirulence agents.
Lithium Bromide/Triethylamine Induced Cycloaddition of N-Alkylidene 2-Amino Esters and Amides to Electron-Deficient Olefins with High Regio- and Stereoselectivity
Tsuge, Otohiko,Kanemasa, Shuji,Yoshioka, Manabu
, p. 1384 - 1391 (2007/10/02)
The imines of 2-amino esters and amides derived from glycine, alanine, and valine are deprotonated by the action of a lithium halide and triethylamine (or DBU).The resulting anionic intermediates undergo highly regio- and stereoselective cycloadditions with a variety of olefins activated by carbonyl-type substituents to produce stereochemically defined derivatives of proline esters or amides.The scope and limitations of this novel cycloaddition are discussed.
