Document Detail


Synthesis of novel glycophanes derived from glucuronic acid by ring closing alkene and alkyne metathesis.
MedLine Citation:
PMID:  18619584     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Cyclophanes and their analogues are of interest in bioactive molecule development and in biomimetic, supramolecular and materials chemistry. Novel hybrids of sugars and cyclophanes (glycophanes) have been prepared via the coupling of alkenyl and alkynyl glucopyranosiduronic acids with phenylene-1,4-diamine and xylene-1,4-diamine and subsequent intramolecular metathesis. Structural studies showed that the geometric arrangements of the sugar groups in the macrocycles containing secondary amides differ from those in macrocycles that contain tertiary amides. This is due to the amides adopting different configurational preferences. The compounds had low solubility in water, precluding an investigation of their recognition phenomena in this medium.
Authors:
Dearbhla Doyle; Paul V Murphy
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2008-06-14
Journal Detail:
Title:  Carbohydrate research     Volume:  343     ISSN:  0008-6215     ISO Abbreviation:  Carbohydr. Res.     Publication Date:  2008 Oct 
Date Detail:
Created Date:  2008-09-15     Completed Date:  2008-12-01     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0043535     Medline TA:  Carbohydr Res     Country:  Netherlands    
Other Details:
Languages:  eng     Pagination:  2535-44     Citation Subset:  IM    
Affiliation:
Centre for Synthesis and Chemical Biology, Conway Institute of Biomolecular and Biomedical Research, University College Dublin, Belfield, Dublin 4, Ireland.
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MeSH Terms
Descriptor/Qualifier:
Alkenes / chemistry*
Carbohydrate Conformation
Carbohydrates / chemical synthesis*,  chemistry
Catalysis
Chemistry / methods
Glucuronic Acid / chemistry*
Glycosides / chemical synthesis*
Hydrogen / chemistry
Magnetic Resonance Spectroscopy
Materials Testing
Models, Chemical
Molecular Conformation
Phenylenediamines / chemical synthesis*
Chemical
Reg. No./Substance:
0/Alkenes; 0/Carbohydrates; 0/Glycosides; 0/Phenylenediamines; 1333-74-0/Hydrogen; 576-37-4/Glucuronic Acid

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