Synthesis and structural characterisation as 12-helix of the hexamer of a beta-amino acid tethered to a pyrrolidin-2-one ring.
Starting from (3S,4R,1'S)-3-amino-2-oxo-1-[1'-(4-methoxyphenylethyl)]pyrrolidine carboxylic acid (2), the first synthesis of a beta-foldamer containing pyrrolidin-2-one rings is described, whose 12-helix conformation is assigned by NMR analysis and confirmed by molecular dynamics (MD) simulations.
Menegazzo
Ileana
I
Dipartimento di Scienze Chimiche, Università di Padova, ICB-CNR, Via Marzolo 1, I-35131 Padova, Italy.
Fries
Alexander
A
Mammi
Stefano
S
Galeazzi
Roberta
R
Martelli
Gianluca
G
Orena
Mario
M
Rinaldi
Samuele
S
D000596:Amino Acids / Q000737:chemistry*; D001559:Benzhydryl Compounds; D002264:Carboxylic Acids / Q000737:chemistry*; D003510:Cyclohexanes / Q000737:chemistry*; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D011759:Pyrrolidines / Q000737:chemistry*; D011760:Pyrrolidinones / Q000737:chemistry*; D012680:Sensitivity and Specificity; D000098704:Bisphenols
D000596:Amino Acids; D001559:Benzhydryl Compounds; D002264:Carboxylic Acids; D003510:Cyclohexanes; D011759:Pyrrolidines; D011760:Pyrrolidinones; C517112:(3S,4R,1'S)-3-amino-2-oxo-1-(1'-(4-methoxyphenylethyl))pyrrolidine carboxylic acid; C517113:bisphenol Z; D000098704:Bisphenols