Document Detail


Molecular scaffold for the construction of three-armed and cage-like receptors.
MedLine Citation:
PMID:  16130155     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
An efficient procedure was developed for the synthesis of the C3-symmetric molecular scaffold 2. The latter can easily be converted by a single step into either the three-armed receptors 11-16 or the cage-like receptor 17. X-ray structures were obtained for 2, 11, and 16, which are discussed in regard to their aptitude as receptor platforms. The interaction of the three-armed receptors 12-16 and the cage-like receptor 17 with phloroglucinol was investigated. In accordance with the conclusions obtained from molecular modeling and X-ray crystallographic studies on the host-guest complexes, the three-armed bipyridine receptor 16 exhibits, due to its induced fit, a larger association constant toward phloroglucinol than the cage 17. This new receptor system shows all of the positive features characteristic of 2,4,6-trialkylbenzene receptor systems, such as conformational control by steric gearing, ready availability, and versatility in derivatization. These attributes, combined with the advantageous size of the components, allows this system to be readily tailored to provide receptors for larger, biologically important molecules.
Authors:
Gebhard Haberhauer; Thomas Oeser; Frank Rominger
Related Documents :
16857665 - Fluorescent indicators distributed throughout the pharmacophore of cholecystokinin prov...
20971005 - Receptor agonists of macrophage migration inhibitory factor.
14522055 - Synthetic compound libraries displayed on the surface of encoded bacteriophage.
22118425 - Notch1 receptor as a marker of lymph node metastases in papillary thyroid cancer.
8675805 - A regulatory role in mammalian salivary glands for 5-hydroxytryptamine receptors couple...
16857665 - Fluorescent indicators distributed throughout the pharmacophore of cholecystokinin prov...
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Chemistry (Weinheim an der Bergstrasse, Germany)     Volume:  11     ISSN:  0947-6539     ISO Abbreviation:  Chemistry     Publication Date:  2005 Nov 
Date Detail:
Created Date:  2005-11-02     Completed Date:  2006-04-17     Revised Date:  2009-08-04    
Medline Journal Info:
Nlm Unique ID:  9513783     Medline TA:  Chemistry     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  6718-26     Citation Subset:  IM    
Affiliation:
Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany. gebhard.haberhauer@urz.uni-heidelberg.de
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Descriptor/Qualifier:
Crystallography, X-Ray
Models, Molecular
Molecular Conformation
Pyridines / chemical synthesis*,  chemistry
Chemical
Reg. No./Substance:
0/Pyridines

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


Previous Document:  Haloacyl complexes of boron, [(CF3)3BC(O)Hal]- (Hal=F, Cl, Br, I).
Next Document:  The mechanism of formamide hydrolysis in water from ab initio calculations and simulations.