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13C CP MAS NMR study of ureido sugars, derivatives of 2-amino-2-deoxy-β-d-glucopyranose and dipeptides

✍ Scribed by I. Wawer; B. Piekarska-Bartoszewicz; A. Temeriusz; M. Potrzebowski; W. Ciesielski

Book ID
104357955
Publisher
Elsevier Science
Year
1998
Tongue
English
Weight
167 KB
Volume
12
Category
Article
ISSN
0926-2040

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✦ Synopsis

3 C CP MAS NMR spectra of solid methyl 3,4,6-tri-O-acetyl-2-deoxy-2-ureido-b-D-glucopyranosides with dipeptide

Ž

. residues protected by OMe, OEt or OBz group were recorded. Broader resonances enabled assignment of carbons linked to nitrogen. Chemical shifts of sugar carbons varied within 2-6 ppm although the acetylated glucose moiety is the same in all compounds. From the six carbonyl groups in the molecule only the resonances of N6-C55O are shifted by 2.9-8.3 ppm downfield in the spectra of solid compounds, comparing to the solution, indicating that the molecules are linked by NH PPP O5C5 hydrogen bonds. The C25O group of ureido bridge is not involved in H-bonding, ester group probably forms intramolecular H-bonds.

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