Molecular recognition studies on naphthyridine derivatives

The association constants Kb of three hosts I-III designed to have both enhanced hydrogen bonding donor strength and conformational preorganization with biotin analogues 1-5 are reported. 1H-NMR titrations under two different concentration conditions have been employed to determine the association c...

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Bibliographic Details
Published inMolecules (Basel, Switzerland) Vol. 15; no. 3; pp. 1213 - 1222
Main Authors Iglesias-Sánchez, José Carlos, Santa María, Dolores, Claramunt, Rosa M, Elguero, José
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 03.03.2010
Molecular Diversity Preservation International
Subjects
acridine
Binding Sites
biotin
host-guest
Hydrogen Bonding
Magnetic Resonance Spectroscopy
naphthyridine
Naphthyridines - chemistry
NMR titrations
Madrid Spain
Spain
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Summary:The association constants Kb of three hosts I-III designed to have both enhanced hydrogen bonding donor strength and conformational preorganization with biotin analogues 1-5 are reported. 1H-NMR titrations under two different concentration conditions have been employed to determine the association constants Kb. A statistical analysis using a presence absence matrix has been applied to calculate the different contributions. Hydrogen bond interactions make naphthyridine derivatives II and III potent binders and effective receptors for (+)-biotin methyl ester (1), due to the complex stabilization by additional hydrogen bonds.
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules15031213