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Alkyne-linked 2,2-disubstituted-indolin-3-one oligomers as extended beta-strand mimetics.

ABSTRACT: The design, synthesis, and structural analysis of a new foldamer that mimics an extended beta-sheet are presented. The nonpeptidic mimetic is based on a series of 2,2-disubstituted-indolin-3-one groups linked through their 4,7-positions by an alkyne spacer. An intramolecular hydrogen bond between the carbonyl of one indolinone subunit and the proximal NH of another subunit imposes a conformation that mimics the side chain positioning on a beta-strand. X-ray crystallographic studies support the presence of this intramolecular hydrogen bond. The described approach allows extension of the scaffold to longer oligomers that will form the basis of new mimetics for the disruption of therapeutically relevant protein-protein interactions that rely on the contacts of side chain residues on two beta-strands.

SUBMITTER: Wyrembak PN

PROVIDER: S-EPMC2767320 | biostudies-literature | 2009 Apr

REPOSITORIES: biostudies-literature

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Alkyne-linked 2,2-disubstituted-indolin-3-one oligomers as extended beta-strand mimetics.

Wyrembak Pauline N PN Hamilton Andrew D AD

Journal of the American Chemical Society 20090401 13

The design, synthesis, and structural analysis of a new foldamer that mimics an extended beta-sheet are presented. The nonpeptidic mimetic is based on a series of 2,2-disubstituted-indolin-3-one groups linked through their 4,7-positions by an alkyne spacer. An intramolecular hydrogen bond between the carbonyl of one indolinone subunit and the proximal NH of another subunit imposes a conformation that mimics the side chain positioning on a beta-strand. X-ray crystallographic studies support the p ...[more]

PMID: 19284758

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