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Organic & Biomolecular Chemistry Vol -6

Organic & Biomolecular Chemistry Vol -5

Organic & Biomolecular Chemistry Vol -4

Organic & Biomolecular Chemistry Vol -3

Organic & Biomolecular Chemistry Vol -2

Metal-mediated base pairing within the simplified nucleic acid GNA

Content Provider	Royal Society of Chemistry (RSC)
Author	Schlegel, Mark K. Pagano, Nicholas Meggers, Eric Zhang, Lilu
Copyright Year	2009
Abstract	Hydroxypyridone and pyridopurine homo- and hetero-base pairs have been investigated in the context of duplex GNA (glycol nucleic acid). Phosphoramidites for automated GNA solid phase synthesis were synthesized economically in a few steps starting from commercially available enantiopure glycidol. Similar to their behavior in DNA, the hydroxypyridone and pyridopurine homo-base pairs display a metal-dependent base pairing, with the hydroxypyridone base pair exhibiting a preference for copper(II) ions and the pyridopurine a preference for nickel(II) ions. However, these metallo-base pairs show modulated properties in GNA with respect to metal-dependent pairing stabilities and metal selectivities. Most interestingly, the hydroxypyridone homo-base pair and hydroxypyridone-pyridopurine hetero-base pair are particularly well accommodated in the GNA duplex and form copper(II)-dependent base pairs that are more stable compared to a Watson-Crick A:T base pair at the same position by nearly 20 °C and 24 °C, respectively. The structure of the copper(II)-hydroxypyridone homo-base pair is discussed based on a recent metallo-GNA duplex crystal structure.
Starting Page	476
Ending Page	482
Page Count	7
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	7
Issue Number	3
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/b816142a
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Glycidol Enantiomer DNA Nickel GNA Hydroxypyridone Glycol nucleic acid Solid-phase synthesis Copper Base pair
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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