Application of Ugi reactions in synthesis of divalent neoglycoconjugates: evidence that the sugars are presented in restricted conformation.
[reaction: see text]. 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.
Bradley
H
H
Chemistry Department, Conway Institute of Biomolecular and Biomedical Research, University College Dublin, Dublin 4, Ireland.
Fitzpatrick
G
G
Glass
W K
WK
Kunz
H
H
Murphy
P V
PV
D002236:Carbohydrate Conformation; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy
D006001:Glycoconjugates