Title
Effect of Methyl Group on Acyclic Serinol Scaffold for Tethering Dyes on DNA Duplex stability
Author
Keiji Murayama, Hiroyuki Asanuma
Year
2016
Journal
ChemBioChem
Abstract
Acyclic serinol derivatives are useful scaffolds for tethering dyes within DNA duplexes. Here we synthesized an inverse L-threoninol (iL-threoninol) scaffold and compared its effect on DNA duplex stability to other acyclic artificial nucleic acid scaffolds that are based on D-threoninol, L-threoninol, and serinol. When planar trans-azobenzene was incorporated into the DNA duplex through a single bulge-like motif (the wedge), the iL-threoninol scaffold stabilized the duplex most efficiently. When scaffolds were incorporated in complementary positions (dimer motif) or in three adjacent positions (cluster motif), D-threoninol was most stabilizing. Circular dichroism spectra indicated that the effect of scaffold on the duplex stability was closely related to the winding induced by each scaffold. When trans-azobenzene was photo-isomerized to non-planar cis-azobenzene, iL-threoninol most strongly destabilized duplex irrespective of the number of artificial residues incorporated. The properties of the iL-threoninol scaffold will make it a useful tether for dyes or other functionalities.
Instrument
J-820
Keywords
Circular dichroism, DNA structure, Stereochemistry, Biochemistry