Beilstein Journal of Organic Chemistry p. 518 - 524 (2011)
Update date:2022-08-11
Topics:
Griesbeck, Axel G.
Neudoerfl, Joerg
Kiff, Alan De
The photochemistry of phthalimide derivatives of the electron-rich amino acids tyrosine, histidine and tryptophan 8-10 was studied with respect to photoinduced electron-transfer (PET)induced decarboxylation and Norrish II bond cleavage. Whereas exclusive photodecarboxylation of the tyrosine substrate 8 was observed, the histidine compound 9 resulted in a mixture of histamine and preferential Norrish cleavage. The tryptophan derivative 10 is photochemically inert and shows preferential decarboxylation only when induced by intermolecular PET.
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