Metathesis of structurally preorganized bivalent carbohydrates. Synthesis of macrocyclic and oligomeric scaffolds

Organic Letters
Trinidad Velasco-Torrijos, Paul V Murphy

Abstract

[reaction: see text] Bivalent carbohydrate substrates for metathesis were synthesized from glucuronic acid and phenylene-1,4-diamine. The substrate secondary structure depends on whether secondary or tertiary amides are present, and this influences the course of the metathesis reaction leading to novel multivalent scaffolding. Molecular modeling suggests that a very rigid macrocyclic scaffold has potential for the development of alpha-helix peptidomimetics.

References

Feb 20, 2004·Chemical Communications : Chem Comm·Manuela TosinPaul V Murphy

Citations

Jun 2, 2005·Chemical Communications : Chem Comm·Simon Dörner, Bernhard Westermann
Mar 5, 2014·Chemistry : a European Journal·Mark FarrellPaul V Murphy
Jan 5, 2011·Bioorganic & Medicinal Chemistry·Dilip V JarikotePaul V Murphy
Jan 21, 2012·Chemistry : a European Journal·Vicente Martí-CentellesSantiago V Luis
Mar 10, 2011·Chemistry, an Asian Journal·Ryosuke Matsubara, Timothy F Jamison
Jun 6, 2012·TheScientificWorldJournal·Vicente Martí-CentellesSantiago V Luis
May 18, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·René RoyHans-Joachim Gabius

Related Concepts

Sugars
Catalysis
Cyclization
Diamines
Ligands
Oligopeptides
Cyclic Peptides
Molecular Stereochemistry
Protein Conformation, beta-Strand
Crystallography, X-Ray

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