Intramolecular Host-Guest Complexes Of D- And L-Mono-6-Phenylalanyl-Amino-6-Deoxy Cyclomalto-Heptaoses.
Coupling of L- and D-phenylalanine to mono 6-amino-β-cyclodextrin leads to the formation of diastereoisomeric intramolecular inclusion compounds.The proton NMR spectra of the two products show clear chiral discrimination between the two molecules with regard to the interaction of the aromatic moieties with the cyclodextrin cavity.
Parrot-Lopez, Helene,Galons, Herve,Coleman, Anthony W.,Djedaini, Florence,Keller, Nelly,Perly, Bruno
Potential formation of intramolecular inclusion complexes in peptidocyclodextrins as evidenced by NMR spectroscopy
Investigations of the structure of β- and γ-cyclodextrin derivatives in solution obtained by grafting amino acids or peptides are presented.These compounds are models for vectorization-dedicated molecular carriers.It is shown that for some amino acids, strong intramolecular self-inclusion complexes are formed in aqueous solution.This process strongly depends upon the nature and position of the pertinent amino acid in the peptide sequence.Two dimensional NMR experiments are used in conjunction with competition with external guests to evidence and estimate the strength of these auto-inclusion complexes.
Djedaini-Pilard, Florence,Azaroual-Bellanger, Nathalie,Gosnat, Muriel,Vernet, Delphine,Perly, Bruno
p. 723 - 730
(2007/10/02)
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