Peptidoglycan-Related Disaccharide-Dipeptides: Differentiation Between Glutaminyl and Isoglutaminyl Residues by NMR Spectroscopy

Autor:	D. Keglevi, J. Kidrič
Rok vydání:	1992
Předmět:	Isoglutamine Dipeptide Stereochemistry Organic Chemistry Disaccharide Nuclear magnetic resonance spectroscopy Carbon-13 NMR Biochemistry carbohydrates (lipids) chemistry.chemical_compound Residue (chemistry) chemistry Structural isomer Peptidoglycan
Zdroj:	Journal of Carbohydrate Chemistry. 11:119-136
ISSN:	1532-2327 0732-8303
Popis:	In order to confirm that tert-butyl ester protection at the isoglutaminyl residue prevents the base-catalyzed iso-glutamine = glutamine rearrangement in title compounds, 6-0-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-N-acetylmura-moyl-L-alanyl-D-glutamine (7) was synthesized from α-benzyl glycoside of 6-0-(2-acetamido-3,4,6-tri-0-acetyl-2-deoxy-β-D-glucopyranosyl)-N-acetylmuramic acid (2) and Z-L-Ala-D-Glu(NH2)OBut via its α-tert-butyl ester 5. 1H and 13C NMR measurements were carried out with regioisomeric [β-GlcNAc-(1-→6)-MurNAc]-L-Ala-D-glutamine and -isoglutamine derivatives; the presented data show differences that enable distinction between the sugar-peptide regioisomers.
Databáze:	OpenAIRE
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