Photoinduced electron-transfer chemistry of the bielectrophoric N-phthaloyl derivatives of the amino acids tyrosine, histidine and tryptophan

AG Griesbeck, J Neudörfl…

Index: Griesbeck, Axel G.; Neudoerfl, Joerg; Kiff, Alan De Beilstein Journal of Organic Chemistry, 2011 , vol. 7, p. 518 - 524

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Citation Number: 15

Abstract

Abstract 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 ...