Diazo Compounds: Versatile Tools for Chemical Biology

ACS Chem Biol. 2016 Dec 16;11(12):3233-3244. doi: 10.1021/acschembio.6b00810. Epub 2016 Oct 26.

Abstract

Diazo groups have broad and tunable reactivity. That and other attributes endow diazo compounds with the potential to be valuable reagents for chemical biologists. The presence of diazo groups in natural products underscores their metabolic stability and anticipates their utility in a biological context. The chemoselectivity of diazo groups, even in the presence of azido groups, presents many opportunities. Already, diazo compounds have served as chemical probes and elicited novel modifications of proteins and nucleic acids. Here, we review advances that have facilitated the chemical synthesis of diazo compounds, and we highlight applications of diazo compounds in the detection and modification of biomolecules.

Publication types

  • Research Support, N.I.H., Extramural
  • Review

MeSH terms

  • Alkylation
  • Amino Acids / chemical synthesis
  • Amino Acids / chemistry
  • Animals
  • Biochemistry / methods
  • Biological Products / chemical synthesis
  • Biological Products / chemistry*
  • Cycloaddition Reaction / methods
  • Diazonium Compounds / chemical synthesis
  • Diazonium Compounds / chemistry*
  • Humans
  • Indicators and Reagents / chemical synthesis
  • Indicators and Reagents / chemistry
  • Models, Molecular
  • Nucleic Acids / chemistry*
  • Proteins / chemistry*

Substances

  • Amino Acids
  • Biological Products
  • Diazonium Compounds
  • Indicators and Reagents
  • Nucleic Acids
  • Proteins