The Mechanism of Ureido-Pyrimidinone:2,7-Diamido-Naphthyridine Complexation and the Presence of Kinetically Controlled Pathways in Multicomponent Hydrogen-Bonded Systems

The Mechanism of Ureido-Pyrimidinone:2,7-Diamido-Naphthyridine Complexation and the Presence of Kinetically Controlled Pathways in Multicomponent Hydrogen-Bonded Systems

The kinetics of association of ureido-pyrimidinone (U) dimers, present either in the 4[1H]-keto form or in the pyrimidin-4-ol form, with 2,7-diamido-1,8-naphthyridine (N) into a complementary heterodimer have been investigated. The formation of heterodimers with 2,7-diamido-1,8-naphthyridine from py...

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Veröffentlicht in:Journal of the American Chemical Society 2008-04, Vol.130 (16), p.5479-5486
Hauptverfasser: de Greef, Tom F. A, Ligthart, G. B. W. L, Lutz, Martin, Spek, Anthony L, Meijer, E. W, Sijbesma, Rint P
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Sprache:eng
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Binding Sites
Diamide - analogs & derivatives
Dimerization
Hydrogen Bonding
Kinetics
Naphthyridines - chemistry
Pyrimidinones - chemistry
Urea - analogs & derivatives
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container_end_page 5486
container_issue 16
container_start_page 5479
container_title Journal of the American Chemical Society
container_volume 130
creator de Greef, Tom F. A
Ligthart, G. B. W. L
Lutz, Martin
Spek, Anthony L
Meijer, E. W
Sijbesma, Rint P
description The kinetics of association of ureido-pyrimidinone (U) dimers, present either in the 4[1H]-keto form or in the pyrimidin-4-ol form, with 2,7-diamido-1,8-naphthyridine (N) into a complementary heterodimer have been investigated. The formation of heterodimers with 2,7-diamido-1,8-naphthyridine from pyrimidin-4-ol dimers is much faster than from 4[1H]-pyrimidinone dimers. Using a combination of simple measurements and simulations, evidence for a bimolecular tautomerization step is presented. Finally, the acquired kinetic knowledge of the different pathways leading from ureido-pyrimidinone homodimers to ureido-pyrimidinone:diamido-naphthyridine (U:N) heterodimers allows the prediction and observation of kinetically determined ureido-pyrimidinone heterodimers which slowly convert back to the corresponding homodimers.
doi_str_mv 10.1021/ja709971y
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W</au><au>Sijbesma, Rint P</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The Mechanism of Ureido-Pyrimidinone:2,7-Diamido-Naphthyridine Complexation and the Presence of Kinetically Controlled Pathways in Multicomponent Hydrogen-Bonded Systems</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2008-04-23</date><risdate>2008</risdate><volume>130</volume><issue>16</issue><spage>5479</spage><epage>5486</epage><pages>5479-5486</pages><issn>0002-7863</issn><issn>1272-7863</issn><eissn>1520-5126</eissn><abstract>The kinetics of association of ureido-pyrimidinone (U) dimers, present either in the 4[1H]-keto form or in the pyrimidin-4-ol form, with 2,7-diamido-1,8-naphthyridine (N) into a complementary heterodimer have been investigated. The formation of heterodimers with 2,7-diamido-1,8-naphthyridine from pyrimidin-4-ol dimers is much faster than from 4[1H]-pyrimidinone dimers. Using a combination of simple measurements and simulations, evidence for a bimolecular tautomerization step is presented. Finally, the acquired kinetic knowledge of the different pathways leading from ureido-pyrimidinone homodimers to ureido-pyrimidinone:diamido-naphthyridine (U:N) heterodimers allows the prediction and observation of kinetically determined ureido-pyrimidinone heterodimers which slowly convert back to the corresponding homodimers.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>18373340</pmid><doi>10.1021/ja709971y</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record>
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subjects Binding Sites
Diamide - analogs & derivatives
Dimerization
Hydrogen Bonding
Kinetics
Naphthyridines - chemistry
Pyrimidinones - chemistry
Urea - analogs & derivatives
title The Mechanism of Ureido-Pyrimidinone:2,7-Diamido-Naphthyridine Complexation and the Presence of Kinetically Controlled Pathways in Multicomponent Hydrogen-Bonded Systems
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