title: Synthesis of α, β-unsaturated γ-amino esters with unprecedented high (E)-stereoselectivity and their conformational analysis in peptides.
abstract: Mild, efficient and racemization-free synthesis of N-protected α, β-unsaturated γ-amino esters with unprecedented high E- stereoselectivity is described. This method is found to be compatible with Boc-, Fmoc- and other side chain protecting groups. The crystal conformations of the vinylogous γ-amino esters in monomers and in homo- and mixed dipeptides are studied. Further, the vinylogous homo-dipeptide showed a β-sheet conformation, while mixed α- and α,β-unsaturated γ-hybrid dipeptide adapted an irregular structure in single crystals.
authors.affiliation: Department of Chemistry Indian Institute of Science Education and Research, Garware Circle Pashan, Pune, Maharashtra 411021, India.
authors.forename: Sachitanand M
authors.initials: SM
authors.lastname: Mali
authors.forename: Anupam
authors.initials: A
authors.lastname: Bandyopadhyay
authors.forename: Sandip V
authors.initials: SV
authors.lastname: Jadhav
authors.forename: Mothukuri Ganesh
authors.initials: MG
authors.lastname: Kumar
authors.forename: Hosahudya N
authors.initials: HN
authors.lastname: Gopi
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D018360:Crystallography, X-Ray; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D004952:Esters; D010455:Peptides