Sequence-specific association in aqueous media by integrating hydrogen bonding and dynamic covalent interactions.
Oligoamide strands that associate in a sequence-specific fashion into hydrogen-bonded duplexes in nonpolar solvents were converted into disulfide cross-linked duplexes in aqueous media. Thus, by incorporating trityl-protected thiol groups, which allows the reversible formation of disulfide bonds, into the oligoamide strands, only duplexes consisting of complementary hydrogen-bonding sequences were formed in aqueous solution as well as in methanol. The sequence-specific cross-linking of oligoamide strands was confirmed by MALDI-TOF, reverse-phase HPLC, and by isolating a cross-linked duplex. This study demonstrates that the sequence-specificity characteristic of multiply hydrogen-bonded systems can be extended into competitive media through the interplay of H-bonding and reversible covalent interactions, based on which a new class of molecular associating and ligating units that are compatible with both polar and nonpolar environments can be conveniently obtained.
Li
Minfeng
M
Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, NY 14260, USA.
Yamato
Kazuhiro
K
Ferguson
Joseph S
JS
Gong
Bing
B
D000577:Amides / Q000737:chemistry*; D004220:Disulfides / Q000737:chemistry; D006860:Hydrogen Bonding; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D014867:Water / Q000737:chemistry
D000577:Amides; D004220:Disulfides; D014867:Water