Conformational change of spermidine upon interaction with adenosine triphosphate in aqueous solution

Keisuke Maruyoshi, Kaori Nonaka, Takeshi Sagane, Tetsuo Demura, Toshiyuki Yamaguchi, Nobuaki Matsumori, Tohru Oishi, Michio Murata

研究成果: ジャーナルへの寄稿記事

7 引用 (Scopus)

抄録

Endogenous polyamines, represented by putrescine, spermidine, and spermine, are known to exert their physiological functions by interacting with polyanionic biomolecules such as DNA, RNA, adenosine triphosphate (ATP), and phospholipids. Very few examples of conformation analysis have been reported for these highly flexible polymethylene compounds, mainly due to the lack of appropriate methodologies. To understand the molecular basis of the weak interaction between polyamines and polyanions that underlies their physiological functions, we aimed to elucidate the solution conformation of spermidine by using diastereospecifically deuterated and 13C-labeled derivatives (1-7), which were designed to diagnose the orientation of seven conformationally relevant bonds in spermidine. 1H-1H and 13C-1H NMR coupling constants (3JH,H and 3JC,H) were successfully determined for a spermidine-ATP complex. The relevant coupling constants markedly decreased upon complexation. The results reveal that spermidine, when interacting with ATP, undergoes changes that make the conformation more bent and forms the complex with the triphosphate part of ATP in an orientation-sensitive manner.

元の言語英語
ページ(範囲)1618-1626
ページ数9
ジャーナルChemistry - A European Journal
15
発行部数7
DOI
出版物ステータス出版済み - 2 2 2009
外部発表Yes

Fingerprint

Spermidine
Conformations
Adenosine Triphosphate
Polyamines
Phospholipids
Biomolecules
Complexation
RNA
DNA
Nuclear magnetic resonance
Putrescine
Spermine
Derivatives

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

これを引用

Conformational change of spermidine upon interaction with adenosine triphosphate in aqueous solution. / Maruyoshi, Keisuke; Nonaka, Kaori; Sagane, Takeshi; Demura, Tetsuo; Yamaguchi, Toshiyuki; Matsumori, Nobuaki; Oishi, Tohru; Murata, Michio.

:: Chemistry - A European Journal, 巻 15, 番号 7, 02.02.2009, p. 1618-1626.

研究成果: ジャーナルへの寄稿記事

Maruyoshi, Keisuke ; Nonaka, Kaori ; Sagane, Takeshi ; Demura, Tetsuo ; Yamaguchi, Toshiyuki ; Matsumori, Nobuaki ; Oishi, Tohru ; Murata, Michio. / Conformational change of spermidine upon interaction with adenosine triphosphate in aqueous solution. :: Chemistry - A European Journal. 2009 ; 巻 15, 番号 7. pp. 1618-1626.
@article{0c35a481105540b6b3568e27da990898,
title = "Conformational change of spermidine upon interaction with adenosine triphosphate in aqueous solution",
abstract = "Endogenous polyamines, represented by putrescine, spermidine, and spermine, are known to exert their physiological functions by interacting with polyanionic biomolecules such as DNA, RNA, adenosine triphosphate (ATP), and phospholipids. Very few examples of conformation analysis have been reported for these highly flexible polymethylene compounds, mainly due to the lack of appropriate methodologies. To understand the molecular basis of the weak interaction between polyamines and polyanions that underlies their physiological functions, we aimed to elucidate the solution conformation of spermidine by using diastereospecifically deuterated and 13C-labeled derivatives (1-7), which were designed to diagnose the orientation of seven conformationally relevant bonds in spermidine. 1H-1H and 13C-1H NMR coupling constants (3JH,H and 3JC,H) were successfully determined for a spermidine-ATP complex. The relevant coupling constants markedly decreased upon complexation. The results reveal that spermidine, when interacting with ATP, undergoes changes that make the conformation more bent and forms the complex with the triphosphate part of ATP in an orientation-sensitive manner.",
author = "Keisuke Maruyoshi and Kaori Nonaka and Takeshi Sagane and Tetsuo Demura and Toshiyuki Yamaguchi and Nobuaki Matsumori and Tohru Oishi and Michio Murata",
year = "2009",
month = "2",
day = "2",
doi = "10.1002/chem.200801961",
language = "English",
volume = "15",
pages = "1618--1626",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "7",

}

TY - JOUR

T1 - Conformational change of spermidine upon interaction with adenosine triphosphate in aqueous solution

AU - Maruyoshi, Keisuke

AU - Nonaka, Kaori

AU - Sagane, Takeshi

AU - Demura, Tetsuo

AU - Yamaguchi, Toshiyuki

AU - Matsumori, Nobuaki

AU - Oishi, Tohru

AU - Murata, Michio

PY - 2009/2/2

Y1 - 2009/2/2

N2 - Endogenous polyamines, represented by putrescine, spermidine, and spermine, are known to exert their physiological functions by interacting with polyanionic biomolecules such as DNA, RNA, adenosine triphosphate (ATP), and phospholipids. Very few examples of conformation analysis have been reported for these highly flexible polymethylene compounds, mainly due to the lack of appropriate methodologies. To understand the molecular basis of the weak interaction between polyamines and polyanions that underlies their physiological functions, we aimed to elucidate the solution conformation of spermidine by using diastereospecifically deuterated and 13C-labeled derivatives (1-7), which were designed to diagnose the orientation of seven conformationally relevant bonds in spermidine. 1H-1H and 13C-1H NMR coupling constants (3JH,H and 3JC,H) were successfully determined for a spermidine-ATP complex. The relevant coupling constants markedly decreased upon complexation. The results reveal that spermidine, when interacting with ATP, undergoes changes that make the conformation more bent and forms the complex with the triphosphate part of ATP in an orientation-sensitive manner.

AB - Endogenous polyamines, represented by putrescine, spermidine, and spermine, are known to exert their physiological functions by interacting with polyanionic biomolecules such as DNA, RNA, adenosine triphosphate (ATP), and phospholipids. Very few examples of conformation analysis have been reported for these highly flexible polymethylene compounds, mainly due to the lack of appropriate methodologies. To understand the molecular basis of the weak interaction between polyamines and polyanions that underlies their physiological functions, we aimed to elucidate the solution conformation of spermidine by using diastereospecifically deuterated and 13C-labeled derivatives (1-7), which were designed to diagnose the orientation of seven conformationally relevant bonds in spermidine. 1H-1H and 13C-1H NMR coupling constants (3JH,H and 3JC,H) were successfully determined for a spermidine-ATP complex. The relevant coupling constants markedly decreased upon complexation. The results reveal that spermidine, when interacting with ATP, undergoes changes that make the conformation more bent and forms the complex with the triphosphate part of ATP in an orientation-sensitive manner.

UR - http://www.scopus.com/inward/record.url?scp=60749104709&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=60749104709&partnerID=8YFLogxK

U2 - 10.1002/chem.200801961

DO - 10.1002/chem.200801961

M3 - Article

C2 - 19130510

AN - SCOPUS:60749104709

VL - 15

SP - 1618

EP - 1626

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 7

ER -