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Issue 42, 2014
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Regioselective opening of unsymmetrical cyclic anhydrides: synthesis of N-glycosylated isoasparagine and isoglutamine conjugates

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Abstract

N-Glycopeptide mimetic with N-glycosylated isoasparagine and isoglutamine conjugates were synthesized by regioselective opening of unsymmetrical cyclic anhydride derivatives of L-aspartic acid and L-glutamic acid, using per-O-acetylated β-D-glycopyranosyl amine. The α-chloro derivative gave a mixture of asparagine and isoasparagine linked glycoconjugates, whereas the trifluoroacetamide derivatives gave predominantly the isoasparagine and isoglutamine linked glycoconjugates as the product. The X-ray crystal structure of the α-chloro isoasparagine linked glycoconjugate showed unique pattern of hydrogen bonding.

Graphical abstract: Regioselective opening of unsymmetrical cyclic anhydrides: synthesis of N-glycosylated isoasparagine and isoglutamine conjugates

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Publication details

The article was received on 12 Feb 2014, accepted on 20 Mar 2014 and first published on 20 Mar 2014


Article type: Paper
DOI: 10.1039/C4RA01234H
Citation: RSC Adv., 2014,4, 22042-22047
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    Regioselective opening of unsymmetrical cyclic anhydrides: synthesis of N-glycosylated isoasparagine and isoglutamine conjugates

    L. Sahoo, A. Singhamahapatra, V. Ramkumar and D. Loganathan, RSC Adv., 2014, 4, 22042
    DOI: 10.1039/C4RA01234H

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