Template-Assisted Preferential Formation of a Syn Photodimer in a Pyrophosphate-Induced Self-Assembly of a Thymine-Functionalized Isothiouronium Receptor

Yuichi Kato; Seiichi Nishizawa; Norio Teramae

doi:10.1021/ol0268485

Template-Assisted Preferential Formation of a Syn Photodimer in a Pyrophosphate-Induced Self-Assembly of a Thymine-Functionalized Isothiouronium Receptor

Yuichi Kato, Seiichi Nishizawa, Norio Teramae

SCI - Chemistry

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

18 Citations (Scopus)

Abstract

(Matrix Presented) The effect of anion templation is investigated for the photodimerization of a thymine-functionalized isothiouronium receptor. The receptor forms a photodimer at the thymine moiety in methanol upon UV irradiation, while the isothiouronium moiety works as an oxoanion binding site via a two-point hydrogen-bonding motif. As compared to the case of a free receptor, the presence of pyrophosphate (PPi) resulted in the preferential formation of the syn-type photodimer, which would be desirable for recognizing the templated PPi.

Original language	English
Pages (from-to)	4407-4410
Number of pages	4
Journal	Organic letters
Volume	4
Issue number	25
DOIs	https://doi.org/10.1021/ol0268485
Publication status	Published - 2002 Dec 12

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Template-Assisted Preferential Formation of a Syn Photodimer in a Pyrophosphate-Induced Self-Assembly of a Thymine-Functionalized Isothiouronium Receptor",

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author = "Yuichi Kato and Seiichi Nishizawa and Norio Teramae",

year = "2002",

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AU - Nishizawa, Seiichi

AU - Teramae, Norio

PY - 2002/12/12

Y1 - 2002/12/12

N2 - (Matrix Presented) The effect of anion templation is investigated for the photodimerization of a thymine-functionalized isothiouronium receptor. The receptor forms a photodimer at the thymine moiety in methanol upon UV irradiation, while the isothiouronium moiety works as an oxoanion binding site via a two-point hydrogen-bonding motif. As compared to the case of a free receptor, the presence of pyrophosphate (PPi) resulted in the preferential formation of the syn-type photodimer, which would be desirable for recognizing the templated PPi.

AB - (Matrix Presented) The effect of anion templation is investigated for the photodimerization of a thymine-functionalized isothiouronium receptor. The receptor forms a photodimer at the thymine moiety in methanol upon UV irradiation, while the isothiouronium moiety works as an oxoanion binding site via a two-point hydrogen-bonding motif. As compared to the case of a free receptor, the presence of pyrophosphate (PPi) resulted in the preferential formation of the syn-type photodimer, which would be desirable for recognizing the templated PPi.

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Template-Assisted Preferential Formation of a Syn Photodimer in a Pyrophosphate-Induced Self-Assembly of a Thymine-Functionalized Isothiouronium Receptor

Abstract

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