ma801470r_si_002.pdf (6.41 MB)
Saccharide-Linked Ethynylpyridine Oligomers: Primary Structures Encode Chiral Helices
journal contribution
posted on 2008-10-14, 00:00 authored by Hajime Abe, Daisuke Murayama, Fumihiro Kayamori, Masahiko InouyeA series of glycoside-linked oligomeric 2,6-pyridylene−ethynylene
(m-ethynylpyridine) compounds were prepared and studied
for their intramolecular chiral induction. The primary structure of
the oligomers, such as the lengths of ethynylpyridine moieties and
linkers and the types of terminal groups and linked glycosides, was
varied. From circular dichroism (CD) and 1H NMR analyses,
it was found that the intramolecular hydrogen bonds between the glycoside
and ethynylpyridine moieties induced the formation of higher-order,
chiral helices of the oligomers. The sign and strength of CD signals
for the helices were found to depend strongly on the length of ethynylpyridines
and the types of terminal groups and glycosides. These results showed
that the oligomers encode their higher-order structures in their primary
structures.