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Peer reviewed
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KEGLEVIC, D; KIDRIC, J
Journal of carbohydrate chemistry, 19/2/1/, Volume: 11, Issue: 2Journal Article
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(NH 2 )OBu t via its α-tert-butyl ester 5. 1 H and 13 C 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.
