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Download fileSolid Phase Synthesis and Secondary Structural Studies of (1→5) Amide-Linked Sialooligomers1
journal contribution
posted on 23.01.1998, 00:00 authored by Lajos Szabo, Brenda L. Smith, Katherine D. McReynolds, Abby L. Parrill, Edwin R. Morris, Jacquelyn GervayA series of dimeric through octameric (1→5) amide-linked
sialooligomers were prepared using solid-phase peptide methods on Rink resin with Fmoc protecting group
chemistry. The oligomers were
conjugated to ε-amino caproic acid in order to model membrane-bound
conformations. The secondary
structure of the oliogomers was probed with NH/ND exchange rates
determined by NMR, and with
circular dichroism. The combined structural studies show that a
tetramer is required for ordered
secondary structure, and that secondary structure is stabilized upon
elongation to pentameric and
hexameric species. Interestingly, the heptamer shows rapid NH/ND
exchange rates; however,
ordered secondary structure is restored in the octamer. These
studies provide the first evidence
that oligomers composed of constrained carbohydrate-derived amino acids
form stable secondary
structures in water.