Furanose ring conformations in a 1′-alkynyl C-nucleoside and the dinucleotide

Junya Chiba; Wataru Shirato; Yusuke Yamade; Byung Soon Kim; Shinya Matsumoto; Masahiko Inouye

doi:10.1016/j.tet.2012.08.057

Furanose ring conformations in a 1′-alkynyl C-nucleoside and the dinucleotide

Junya Chiba^*, Wataru Shirato, Yusuke Yamade, Byung Soon Kim, Shinya Matsumoto, Masahiko Inouye

^*Corresponding author for this work

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

8 Scopus citations

Abstract

A large-scale synthesis was carried out for alkynyl C-nucleotide oligomers in order to clarify the structural details of the artificial DNA. A liquid-phase synthesis by means of phosphoramidite methodology enabled us to handle ∼0.1 g of the DNA oligomers possessing a pseudouracil derivative (T*) as a non-natural nucleobase. ¹H NMR measurements in aqueous media were carried out for the oligomers, succeeded in the accurate assignments of the protons accompanying with determination of the coupling constants (J values). These J values revealed that average conformation of the alkynylribose rings in the DNA was substantially biased toward the S-type conformers ( ²T ₁/E ₁/ ^OT ₁). X-ray crystal analysis of the non-natural nucleoside also supported the S-type conformation ( ²E/ ²T ₁) as seen in natural B-DNA.

Original language	English
Pages (from-to)	9045-9049
Number of pages	5
Journal	Tetrahedron
Volume	68
Issue number	44
DOIs	https://doi.org/10.1016/j.tet.2012.08.057
State	Published - 2012/11/04

Keywords

Alkynylribose
C-Nucleotide
Pseudorotation
Puckering conformation

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Furanose ring conformations in a 1′-alkynyl C-nucleoside and the dinucleotide",

abstract = "A large-scale synthesis was carried out for alkynyl C-nucleotide oligomers in order to clarify the structural details of the artificial DNA. A liquid-phase synthesis by means of phosphoramidite methodology enabled us to handle ∼0.1 g of the DNA oligomers possessing a pseudouracil derivative (T*) as a non-natural nucleobase. 1H NMR measurements in aqueous media were carried out for the oligomers, succeeded in the accurate assignments of the protons accompanying with determination of the coupling constants (J values). These J values revealed that average conformation of the alkynylribose rings in the DNA was substantially biased toward the S-type conformers ( 2T 1/E 1/ OT 1). X-ray crystal analysis of the non-natural nucleoside also supported the S-type conformation ( 2E/ 2T 1) as seen in natural B-DNA.",

keywords = "Alkynylribose, C-Nucleotide, Pseudorotation, Puckering conformation",

author = "Junya Chiba and Wataru Shirato and Yusuke Yamade and Kim, {Byung Soon} and Shinya Matsumoto and Masahiko Inouye",

note = "Funding Information: This study was performed through Special Coordination Funds for Promoting Science and Technology of the Ministry of Education, Culture, Sports Science and Technology, the Japanese Government . ",

year = "2012",

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doi = "10.1016/j.tet.2012.08.057",

language = "英語",

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T1 - Furanose ring conformations in a 1′-alkynyl C-nucleoside and the dinucleotide

AU - Chiba, Junya

AU - Shirato, Wataru

AU - Yamade, Yusuke

AU - Kim, Byung Soon

AU - Matsumoto, Shinya

AU - Inouye, Masahiko

N1 - Funding Information: This study was performed through Special Coordination Funds for Promoting Science and Technology of the Ministry of Education, Culture, Sports Science and Technology, the Japanese Government .

PY - 2012/11/4

Y1 - 2012/11/4

N2 - A large-scale synthesis was carried out for alkynyl C-nucleotide oligomers in order to clarify the structural details of the artificial DNA. A liquid-phase synthesis by means of phosphoramidite methodology enabled us to handle ∼0.1 g of the DNA oligomers possessing a pseudouracil derivative (T*) as a non-natural nucleobase. 1H NMR measurements in aqueous media were carried out for the oligomers, succeeded in the accurate assignments of the protons accompanying with determination of the coupling constants (J values). These J values revealed that average conformation of the alkynylribose rings in the DNA was substantially biased toward the S-type conformers ( 2T 1/E 1/ OT 1). X-ray crystal analysis of the non-natural nucleoside also supported the S-type conformation ( 2E/ 2T 1) as seen in natural B-DNA.

AB - A large-scale synthesis was carried out for alkynyl C-nucleotide oligomers in order to clarify the structural details of the artificial DNA. A liquid-phase synthesis by means of phosphoramidite methodology enabled us to handle ∼0.1 g of the DNA oligomers possessing a pseudouracil derivative (T*) as a non-natural nucleobase. 1H NMR measurements in aqueous media were carried out for the oligomers, succeeded in the accurate assignments of the protons accompanying with determination of the coupling constants (J values). These J values revealed that average conformation of the alkynylribose rings in the DNA was substantially biased toward the S-type conformers ( 2T 1/E 1/ OT 1). X-ray crystal analysis of the non-natural nucleoside also supported the S-type conformation ( 2E/ 2T 1) as seen in natural B-DNA.

KW - Alkynylribose

KW - C-Nucleotide

KW - Pseudorotation

KW - Puckering conformation

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U2 - 10.1016/j.tet.2012.08.057

DO - 10.1016/j.tet.2012.08.057

M3 - 学術論文

AN - SCOPUS:84866391837

SN - 0040-4020

VL - 68

SP - 9045

EP - 9049

JO - Tetrahedron

JF - Tetrahedron

IS - 44

ER -

Furanose ring conformations in a 1′-alkynyl C-nucleoside and the dinucleotide

Abstract

Keywords

ASJC Scopus subject areas

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