4.7 Article

Click with a boronic acid handle: a neighboring group-assisted click reaction that allows ready secondary functionalization

Journal

CHEMICAL COMMUNICATIONS
Volume 51, Issue 82, Pages 15180-15183

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c5cc05890b

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Funding

  1. National Institutes of Health [GM084933]
  2. Molecular Basis of Disease Program (MBD) at GSU
  3. Graduate Assistance in Areas of National Need (GAANN) Fellowship at GSU
  4. Frontier Scientific Inc.

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The feasibility of a neighboring boronic acid-facilitated facile condensation of an aldehyde is described. This reaction is bio-orthogonal, complete at room temperature within minutes, and suitable for bioconjugation chemistry. The boronic acid group serves the dual purpose of catalyzing the condensation reaction and being a handle for secondary functionalization.

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