Biased helical folding of chiral oligoindole foldamers.
Oligoindole-based chiral foldamers have been synthesized by incorporating (S)- or (R)-1-phenylethylamine to both ends of the tetraindole scaffold. The oligoindoles fold into a helical conformation upon binding an anion by hydrogen bonds, which gives rise to an induced circular dichroism (CD) signal of large amplitude, implying the preferential formation of one helical isomer over another. Theoretical calculations suggest that the (P)-helix of the (S,S)-oligoindole 8a be more energetically stable than the corresponding (M)-helix.
Naidu
Veluru Ramesh
VR
Department of Chemistry, Yonsei University, Seoul-120-749 Korea.
Kim
Min Cheol
MC
Suk
Jae-min
JM
Kim
Ho-Joong
HJ
Lee
Myongsoo
M
Sim
Eunji
E
Jeong
Kyu-Sung
KS
D002942:Circular Dichroism; D007211:Indoles / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D010627:Phenethylamines / Q000737:chemistry; D011108:Polymers / Q000737:chemistry*; D013237:Stereoisomerism
D007211:Indoles; D010627:Phenethylamines; D011108:Polymers