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Synthesis and Reactivity of a Bis-Strained Alkyne Derived from 1,1'-Biphenyl-2,2',6,6'-tetrol.

ABSTRACT: The novel "double strained alkyne" 3 has been prepared and evaluated in strain-promoted azide-alkyne cycloaddition reactions with azides. The X-ray crystallographic structure of 3, which was prepared in one step from 1,1'-biphenyl-2,2',6,6'-tetrol 4, reveals the strained nature of the alkynes. Dialkyne 3 undergoes cycloaddition reactions with a number of azides, giving mixtures of regiosiomeric products in excellent yields. The monoaddition products were not observed or isolated from the reactions, suggesting that the second cycloaddition proceeds at a faster rate than the first, and this is supported by molecular modeling studies. Dialkyne 3 was successfully employed for "peptide stapling" of a p53-based diazido peptide, whereby two azides are bridged to give a product with a stabilized conformation.

SUBMITTER: Knighton RC 

PROVIDER: S-EPMC6648819 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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Synthesis and Reactivity of a Bis-Strained Alkyne Derived from 1,1'-Biphenyl-2,2',6,6'-tetrol.

Knighton Richard C RC   Sharma Krishna K   Robertson Naomi S NS   Spring David R DR   Wills Martin M  

ACS omega 20190129 1

The novel "double strained alkyne" <b>3</b> has been prepared and evaluated in strain-promoted azide-alkyne cycloaddition reactions with azides. The X-ray crystallographic structure of <b>3</b>, which was prepared in one step from 1,1'-biphenyl-2,2',6,6'-tetrol <b>4</b>, reveals the strained nature of the alkynes. Dialkyne <b>3</b> undergoes cycloaddition reactions with a number of azides, giving mixtures of regiosiomeric products in excellent yields. The monoaddition products were not observed  ...[more]

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