A quadruply hydrogen bonded heterocomplex displaying high-fidelity recognition

Taiho Park; Eric M. Todd; Shoji Nakashima; Steven C. Zimmerman

doi:10.1021/ja0545517

A quadruply hydrogen bonded heterocomplex displaying high-fidelity recognition

Taiho Park, Eric M. Todd, Shoji Nakashima, Steven C. Zimmerman

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

141 Scopus citations

Abstract

An exceptionally strong quadruply hydrogen-bonded complex is formed between 2,7-diamido-1,8-naphthyridine 3 (DAN) and the butylurea of guanosine 6 (UG) in chloroform. The UG unit can be prepared in four steps from guanosine on a 10 g scale in excellent yields without chromatographic purification. The association constant (K_assoc ≈ 5 × 10⁷ M^-1) for the UG·DAN complex determined by fluorescence energy transfer from the naphthyridine unit of 3 to coumarin 343 covalently linked UG (18) is among the highest reported for a neutral DNA base-pair analogue. The weak self-association of DAN (K_dimer < 10 M^-1) and UG (K_dimer ca. 200-300 M^-1) means that the UG·DAN complex forms with unparalleled fidelity.

Original language	English
Pages (from-to)	18133-18142
Number of pages	10
Journal	Journal of the American Chemical Society
Volume	127
Issue number	51
DOIs	https://doi.org/10.1021/ja0545517
State	Published - 28 Dec 2005
Externally published	Yes

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja0545517

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abstract = "An exceptionally strong quadruply hydrogen-bonded complex is formed between 2,7-diamido-1,8-naphthyridine 3 (DAN) and the butylurea of guanosine 6 (UG) in chloroform. The UG unit can be prepared in four steps from guanosine on a 10 g scale in excellent yields without chromatographic purification. The association constant (Kassoc ≈ 5 × 107 M-1) for the UG·DAN complex determined by fluorescence energy transfer from the naphthyridine unit of 3 to coumarin 343 covalently linked UG (18) is among the highest reported for a neutral DNA base-pair analogue. The weak self-association of DAN (Kdimer < 10 M-1) and UG (Kdimer ca. 200-300 M-1) means that the UG·DAN complex forms with unparalleled fidelity.",

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T1 - A quadruply hydrogen bonded heterocomplex displaying high-fidelity recognition

AU - Park, Taiho

AU - Todd, Eric M.

AU - Nakashima, Shoji

AU - Zimmerman, Steven C.

PY - 2005/12/28

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N2 - An exceptionally strong quadruply hydrogen-bonded complex is formed between 2,7-diamido-1,8-naphthyridine 3 (DAN) and the butylurea of guanosine 6 (UG) in chloroform. The UG unit can be prepared in four steps from guanosine on a 10 g scale in excellent yields without chromatographic purification. The association constant (Kassoc ≈ 5 × 107 M-1) for the UG·DAN complex determined by fluorescence energy transfer from the naphthyridine unit of 3 to coumarin 343 covalently linked UG (18) is among the highest reported for a neutral DNA base-pair analogue. The weak self-association of DAN (Kdimer < 10 M-1) and UG (Kdimer ca. 200-300 M-1) means that the UG·DAN complex forms with unparalleled fidelity.

AB - An exceptionally strong quadruply hydrogen-bonded complex is formed between 2,7-diamido-1,8-naphthyridine 3 (DAN) and the butylurea of guanosine 6 (UG) in chloroform. The UG unit can be prepared in four steps from guanosine on a 10 g scale in excellent yields without chromatographic purification. The association constant (Kassoc ≈ 5 × 107 M-1) for the UG·DAN complex determined by fluorescence energy transfer from the naphthyridine unit of 3 to coumarin 343 covalently linked UG (18) is among the highest reported for a neutral DNA base-pair analogue. The weak self-association of DAN (Kdimer < 10 M-1) and UG (Kdimer ca. 200-300 M-1) means that the UG·DAN complex forms with unparalleled fidelity.

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A quadruply hydrogen bonded heterocomplex displaying high-fidelity recognition

Abstract

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