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

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

Author information

1
Department of Chemistry and ‡Department of Biochemistry, University of Wisconsin-Madison , Madison, Wisconsin 53706, United States.

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.

PMID:
26981746
PMCID:
PMC5141246
DOI:
10.1021/acs.orglett.6b00278
[Indexed for MEDLINE]
Free PMC Article

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