A photochemical C=C cleavage process: toward access to backbone N-formyl peptides
Keyword(s):
Photo-responsive modifications and photo-uncaging concepts are useful for spatiotemporal control of peptides structure and function. While side chain photo-responsive modifications are relatively common, access to photo-responsive modifications of backbone N–H bonds is quite limited. This letter describes a new photocleavage pathway, affording N-formyl amides from vinylogous nitroaryl precursors under physiologically relevant conditions via a formal oxidative C=C cleavage. The N-formyl amide products have unique properties and reactivity, but are difficult or impossible to access by traditional synthetic approaches.
2007 ◽
Vol 35
(5)
◽
pp. 870-875
◽
Keyword(s):
2015 ◽
Vol 17
(1)
◽
pp. 4-25
◽
Keyword(s):
2006 ◽
Vol 282
(7)
◽
pp. 4453-4462
◽
1988 ◽
Vol 46
◽
pp. 26-27
Keyword(s):
1992 ◽
Vol 50
(1)
◽
pp. 506-507