Chiral translation and cooperative self-assembly of discrete helical structures using molecular recognition dyads.
Complementary diaminopyridine (DAP) and flavin derivatives self-assemble into discrete helically stacked tetrads in hydrocarbon solvents. The self-assembled structure was demonstrated through induced circular dichroism using DAPs with chiral side-chains and flavin with achiral side-chains. Flavin derivatives with chiral side-chains were synthesized; cooperativity in the self-assembly was established through circular dichroism (CD) profiles and melting curves. It was found that placing stereocenters in both recognition units resulted in a strong bisignated profile and enhancement of complex stability, indicative of cooperative self-assembly.
Nakade
Hiroshi
H
Department of Chemistry, University of Massachusetts, 710 North Pleasant Street, Amherst, MA 01003, USA.
Jordan
Brian J
BJ
Xu
Hao
H
Han
Gang
G
Srivastava
Sudhanshu
S
Arvizo
Rochelle R
RR
Cooke
Graeme
G
Rotello
Vincent M
VM
D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism