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.
Sequence-specific association in aqueous media by integrating hydrogen bonding and dynamic covalent interactions. Publishing Authors By Initials
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Sequence-specific association in aqueous media by integrating hydrogen bonding and dynamic covalent interactions. Journal Published:
PUBLICATION TYPE: Research Support, U.S. Gov't,
Journal: Journal of the American Chemical Society
VOLUME: 128
Page Numbers: 12628-9
Journal Abbreviation: J. Am. Chem. Soc.
ISSN: 0002-7863
DAY: 4
MONTH: Oct
YEAR: 2006
Sequence-specific association in aqueous media by integrating hydrogen bonding and dynamic covalent interactions. Information
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LANGUAGE: eng
NlmUniqueID: 7503056
Sequence-specific association in aqueous media by integrating hydrogen bonding and dynamic covalent interactions. Keywords Mesh Terms:
KEYWORDS: Water
MESH TERMS: chemistry
Chemical & Substance for Abstract: Sequence-specific association in aqueous media by integrating hydrogen bonding and dynamic covalent interactions. Information
Substance Name: Water
Registry Number: 7732-18-5
Grant and Affiliation Information for Sequence-specific association in aqueous media by integrating hydrogen bonding and dynamic covalent interactions.
AFFILIATION: Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, NY 14260, USA.
Country: United States
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MEDLINETA: J Am Chem Soc
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