1,3-Dipolar Cycloadditions of Diazo Compounds in the Presence of Azides

Org Lett. 2016 Apr 1;18(7):1538-41. doi: 10.1021/acs.orglett.6b00278. Epub 2016 Mar 16.


The diazo group has untapped utility in chemical biology. The tolerance of stabilized diazo groups to cellular metabolism is comparable to that of azido groups. However, chemoselectivity has been elusive, as both groups undergo 1,3-dipolar cycloadditions with strained alkynes. Removing strain and tuning dipolarophile electronics yields diazo group selective 1,3-dipolar cycloadditions that can be performed in the presence of an azido group. For example, diazoacetamide but not its azido congener react with dehydroalanine residues, as in the natural product nisin.

Publication types

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

MeSH terms

  • Alanine / analogs & derivatives*
  • Alanine / chemistry
  • Azides / chemistry*
  • Azo Compounds / chemistry*
  • Cycloaddition Reaction
  • Molecular Structure


  • Azides
  • Azo Compounds
  • dehydroalanine
  • Alanine