title: 1,3-Dipolar Cycloadditions of Diazo Compounds in the Presence of Azides.
abstract: 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.
authors.affiliation: Department of Chemistry and ‡Department of Biochemistry, University of Wisconsin-Madison , Madison, Wisconsin 53706, United States.
authors.forename: Matthew R
authors.initials: MR
authors.lastname: Aronoff
authors.affiliation: Department of Chemistry and ‡Department of Biochemistry, University of Wisconsin-Madison , Madison, Wisconsin 53706, United States.
authors.forename: Brian
authors.initials: B
authors.lastname: Gold
authors.affiliation: Department of Chemistry and ‡Department of Biochemistry, University of Wisconsin-Madison , Madison, Wisconsin 53706, United States.
authors.forename: Ronald T
authors.initials: RT
authors.lastname: Raines
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000737:chemistry; D001386:Azides / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry*; D061565:Cycloaddition Reaction; D015394:Molecular Structure
chemical_list: D001386:Azides; D001391:Azo Compounds; C015102:dehydroalanine; D000409:Alanine