Synthesis and structural study of a fully protected α-C-galactosyl model dipeptide

Abstract

The synthesis of three N-alkyl-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-7-[(alkyl-carbonyl)amino]-L-glycero-α-D-galacto-octopyranuronamides6a-c, analogous model dipeptides containing two amide groups connected to the α-carbon bearing the fully protected galactose as a side chain, has been realized with the aim of determining the conformational influence of the galactosyl moiety on the peptide backbone. Molecular modeing of6a, X-ray crystallography of6c and IR and NMR experiments on6a-c in organic solvents show that the carbohydrate ring assumes a twist boat conformation. In non-polar organic solvents, the NH of the left amide group interacts with one ketal oxygen of the galactosyl group.

DOI: 10.1007/BF02443611

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Cite this paper

@article{Coutrot2004SynthesisAS, title={Synthesis and structural study of a fully protected α-C-galactosyl model dipeptide}, author={Fr{\'e}d{\'e}ric Coutrot and Michel Marruad and Bernard Maigret and Claire M Grison and Philippe Coutrot}, journal={Letters in Peptide Science}, year={2004}, volume={8}, pages={107-116} }