Diazo groups endure metabolism and enable chemoselectivity in cellulo

J Am Chem Soc. 2015 Feb 25;137(7):2412-5. doi: 10.1021/ja5095815. Epub 2015 Feb 16.

Abstract

We introduce a stabilized diazo group as a reporter for chemical biology. ManDiaz, which is a diazo derivative of N-acetylmannosamine, is found to endure cellular metabolism and label the surface of a mammalian cell. There its diazo group can undergo a 1,3-dipolar cycloaddition with a strained alkyne, providing a signal comparable to that from the azido congener, ManNAz. The chemoselectivity of diazo and alkynyl groups enables dual labeling of cells that is not possible with azido and alkynyl groups. Thus, the diazo group, which is approximately half the size of an azido group, provides unique opportunities for orthogonal labeling of cellular components.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / metabolism
  • Animals
  • Azo Compounds / chemistry*
  • Azo Compounds / metabolism*
  • CHO Cells
  • Cricetinae
  • Cricetulus
  • Hexosamines / chemistry
  • Substrate Specificity

Substances

  • Alkynes
  • Azo Compounds
  • Hexosamines
  • N-acetylmannosamine