Conformational restriction of cyclic dinucleotides with triazole-linked cyclophane analogues

Tomoko Fujino; Koudai Okada; Hiroyuki Isobe

doi:10.1016/j.tetlet.2014.03.026

Conformational restriction of cyclic dinucleotides with triazole-linked cyclophane analogues

Tomoko Fujino, Koudai Okada, Hiroyuki Isobe

研究成果: Article › 査読

16 被引用数 (Scopus)

抄録

Cyclic dinucleotides (CDN) such as c-di-GMP and c-di-AMP are important multi-functional compounds that regulate a diverse range of processes in bacteria. The diversity of the functions is enabled by the two distinct conformations, that is, open and close conformations. We herein report the concise synthesis of triazole-linked analogues (c-di-GMP^TL, c-di-AMP^TL) through click dimerization of nucleoside analogues. The implementation of a cyclophane system in the central macrocycle furnished the structure with the conformational restriction to maintain the structure similar to the open conformer of natural congeners.

本文言語	English
ページ（範囲）	2659-2661
ページ数	3
ジャーナル	Tetrahedron Letters
巻	55
号	16
DOI	https://doi.org/10.1016/j.tetlet.2014.03.026
出版ステータス	Published - 2014 4月 16
外部発表	はい

ASJC Scopus subject areas

生化学
創薬
有機化学

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10.1016/j.tetlet.2014.03.026

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title = "Conformational restriction of cyclic dinucleotides with triazole-linked cyclophane analogues",

abstract = "Cyclic dinucleotides (CDN) such as c-di-GMP and c-di-AMP are important multi-functional compounds that regulate a diverse range of processes in bacteria. The diversity of the functions is enabled by the two distinct conformations, that is, open and close conformations. We herein report the concise synthesis of triazole-linked analogues (c-di-GMPTL, c-di-AMPTL) through click dimerization of nucleoside analogues. The implementation of a cyclophane system in the central macrocycle furnished the structure with the conformational restriction to maintain the structure similar to the open conformer of natural congeners.",

keywords = "Click chemistry, Conformational restriction, Cyclic dinucleotide, Cyclophane, Triazole",

author = "Tomoko Fujino and Koudai Okada and Hiroyuki Isobe",

note = "Funding Information: This work was partly supported by KAKENHI (Nos. 24241036 and 23550041 ). We thank Research and Analytical Center for Giant Molecules (Tohoku Univ.) for NMR measurements. ",

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doi = "10.1016/j.tetlet.2014.03.026",

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T1 - Conformational restriction of cyclic dinucleotides with triazole-linked cyclophane analogues

AU - Fujino, Tomoko

AU - Okada, Koudai

AU - Isobe, Hiroyuki

N1 - Funding Information: This work was partly supported by KAKENHI (Nos. 24241036 and 23550041 ). We thank Research and Analytical Center for Giant Molecules (Tohoku Univ.) for NMR measurements.

PY - 2014/4/16

Y1 - 2014/4/16

N2 - Cyclic dinucleotides (CDN) such as c-di-GMP and c-di-AMP are important multi-functional compounds that regulate a diverse range of processes in bacteria. The diversity of the functions is enabled by the two distinct conformations, that is, open and close conformations. We herein report the concise synthesis of triazole-linked analogues (c-di-GMPTL, c-di-AMPTL) through click dimerization of nucleoside analogues. The implementation of a cyclophane system in the central macrocycle furnished the structure with the conformational restriction to maintain the structure similar to the open conformer of natural congeners.

AB - Cyclic dinucleotides (CDN) such as c-di-GMP and c-di-AMP are important multi-functional compounds that regulate a diverse range of processes in bacteria. The diversity of the functions is enabled by the two distinct conformations, that is, open and close conformations. We herein report the concise synthesis of triazole-linked analogues (c-di-GMPTL, c-di-AMPTL) through click dimerization of nucleoside analogues. The implementation of a cyclophane system in the central macrocycle furnished the structure with the conformational restriction to maintain the structure similar to the open conformer of natural congeners.

KW - Click chemistry

KW - Conformational restriction

KW - Cyclic dinucleotide

KW - Cyclophane

KW - Triazole

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JO - Tetrahedron Letters

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Conformational restriction of cyclic dinucleotides with triazole-linked cyclophane analogues

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