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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.

SUBMITTER: Aronoff MR

PROVIDER: S-EPMC5141246 | biostudies-literature | 2016 Apr

REPOSITORIES: biostudies-literature

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

Aronoff Matthew R MR Gold Brian B Raines Ronald T RT

Organic letters 20160316 7

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 r ...[more]

PMID: 26981746

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