期刊
ORGANIC LETTERS
卷 18, 期 7, 页码 1538-1541出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b00278
关键词
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资金
- NIH [R01 GM044783, P41 GM103399]
- NSF [CHE-0840494]
- Bender
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.
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