Higher affinity quadruply hydrogen-bonded complexation with 7-deazaguanine urea

Hugo C. Ong; Steven C. Zimmerman

doi:10.1021/ol0601803

Higher affinity quadruply hydrogen-bonded complexation with 7-deazaguanine urea

Hugo C. Ong, Steven C. Zimmerman

Research output: Contribution to journal › Article › peer-review

47 Scopus citations

Abstract

UG forms a highly stable quadruply hydrogen-bonded heterocomplex with DAN, but the fidelity of the complex is lowered somewhat by the Hoogsteen-side oligomerization of UG (K_assoc ∼ 230 M^-1, CDCl ₃). DeUG was prepared as a more robust analogue of UG lacking the Hoogsteen nitrogen atom. Remarkably, the deaza analogue, DeUG, forms a much more stable complex with DAN (>10-fold higher K_assoc for DeUG-DAN vs UG-DAN) but also dimerizes more strongly (K_dim = 880 ± 40 M^-1, CDCl₃) by adopting a conformation preorganized for both binding and dimerization.

Original language	English
Pages (from-to)	1589-1592
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	8
DOIs	https://doi.org/10.1021/ol0601803
State	Published - 13 Apr 2006
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "UG forms a highly stable quadruply hydrogen-bonded heterocomplex with DAN, but the fidelity of the complex is lowered somewhat by the Hoogsteen-side oligomerization of UG (Kassoc ∼ 230 M-1, CDCl 3). DeUG was prepared as a more robust analogue of UG lacking the Hoogsteen nitrogen atom. Remarkably, the deaza analogue, DeUG, forms a much more stable complex with DAN (>10-fold higher Kassoc for DeUG-DAN vs UG-DAN) but also dimerizes more strongly (Kdim = 880 ± 40 M-1, CDCl3) by adopting a conformation preorganized for both binding and dimerization.",

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AU - Ong, Hugo C.

AU - Zimmerman, Steven C.

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N2 - UG forms a highly stable quadruply hydrogen-bonded heterocomplex with DAN, but the fidelity of the complex is lowered somewhat by the Hoogsteen-side oligomerization of UG (Kassoc ∼ 230 M-1, CDCl 3). DeUG was prepared as a more robust analogue of UG lacking the Hoogsteen nitrogen atom. Remarkably, the deaza analogue, DeUG, forms a much more stable complex with DAN (>10-fold higher Kassoc for DeUG-DAN vs UG-DAN) but also dimerizes more strongly (Kdim = 880 ± 40 M-1, CDCl3) by adopting a conformation preorganized for both binding and dimerization.

AB - UG forms a highly stable quadruply hydrogen-bonded heterocomplex with DAN, but the fidelity of the complex is lowered somewhat by the Hoogsteen-side oligomerization of UG (Kassoc ∼ 230 M-1, CDCl 3). DeUG was prepared as a more robust analogue of UG lacking the Hoogsteen nitrogen atom. Remarkably, the deaza analogue, DeUG, forms a much more stable complex with DAN (>10-fold higher Kassoc for DeUG-DAN vs UG-DAN) but also dimerizes more strongly (Kdim = 880 ± 40 M-1, CDCl3) by adopting a conformation preorganized for both binding and dimerization.

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Higher affinity quadruply hydrogen-bonded complexation with 7-deazaguanine urea

Abstract

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