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Application of Ugi Reactions in Synthesis of Divalent Neoglycoconjugates:  Evidence That the Sugars Are Presented in Restricted Conformation

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journal contribution
posted on 02.08.2001 by Helena Bradley, Geraldine Fitzpatrick, W. Kenneth Glass, Horst Kunz, Paul V. Murphy
The Ugi reaction has been used to prepare divalent galactose derivatives. NMR analysis shows that a divalent neoglycoconjugate, where the glycopeptides are bridged by a terephthaloyl group, is an 83:17 mixture of two conformers; the amide groups of the major isomer have E-anti conformations. The spatial relationship and the relative orientation of the sugars are restricted, which may have consequences for the recognition of this and related structures in biological systems.