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Abstract
EDC mediated coupling of the 4-O-succinoyl glycosyl azide 2 with glycosylamine 3 gave the protected glycosylazide 4. Hydrogenation of 4 afforded the glycosylamine 5. Chemoselective hydrolysis of the reducing end glycosylamine, followed by hydrogenation afforded N,N″-diacetylpseudochitotriose 7. Coupling of 5 with heterocyclic or with Cbz protected aliphatic amino acids yielded glycosyl amides 8–12. Deprotection of 11 and 12 afforded the N,N″-diacetylpseudochitotriosyl amides of β-alanine, 13, and l-arginine, 14. Molecular modelling calculations revealed that the pseudotrisaccharides exist in low energy extended conformations which show similar space filling as N,N′,N″-triacetylchitotriose.
*Dedicated to Professor Dr. Joachim Thiem on the occasion of his 60th birthday.
ACKNOWLEDGMENTS
This work was supported by EU grant no. BIO4-CT-960670. MGP acknowledges partial support by the Fonds der Chemischen Industrie. AG thanks the “Studienstiftung des Deutschen Volkes” for a PhD scholarship.
Notes
*Dedicated to Professor Dr. Joachim Thiem on the occasion of his 60th birthday.