Solid Phase Synthesis and Secondary Structural Studies of (1→5) Amide-Linked Sialooligomers

Lajos Szabo, Brenda L. Smith, Katherine D. McReynolds, Abby L. Parrill, Edwin R. Morris, Jacquelyn Gervay-Hague

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Abstract

A 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.

Original languageEnglish (US)
Pages (from-to)1074-1078
Number of pages5
JournalJournal of Organic Chemistry
Volume63
Issue number4
Publication statusPublished - Feb 20 1998
Externally publishedYes

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ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Szabo, L., Smith, B. L., McReynolds, K. D., Parrill, A. L., Morris, E. R., & Gervay-Hague, J. (1998). Solid Phase Synthesis and Secondary Structural Studies of (1→5) Amide-Linked Sialooligomers. Journal of Organic Chemistry, 63(4), 1074-1078.