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

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 substra...

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Main Authors:	Griesbeck, Axel G, Neudörfl, Jörg, de Kiff, Alan
Format:	Online
Language:	English
Published:	Beilstein-Institut 2011
Online Access:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3107463/

id	pubmed-3107463
recordtype	oai_dc
spelling	pubmed-31074632011-06-06 Photoinduced electron-transfer chemistry of the bielectrophoric N-phthaloyl derivatives of the amino acids tyrosine, histidine and tryptophan Griesbeck, Axel G Neudörfl, Jörg de Kiff, Alan Full Research Paper 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. Beilstein-Institut 2011-04-26 /pmc/articles/PMC3107463/ /pubmed/21647325 http://dx.doi.org/10.3762/bjoc.7.60 Text en Copyright © 2011, Griesbeck et al; licensee Beilstein-Institut. http://www.beilstein-journals.org/bjoc This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (http://www.beilstein-journals.org/bjoc)
repository_type	Open Access Journal
institution_category	Foreign Institution
institution	US National Center for Biotechnology Information
building	NCBI PubMed
collection	Online Access
language	English
format	Online
author	Griesbeck, Axel G Neudörfl, Jörg de Kiff, Alan
spellingShingle	Griesbeck, Axel G Neudörfl, Jörg de Kiff, Alan Photoinduced electron-transfer chemistry of the bielectrophoric N-phthaloyl derivatives of the amino acids tyrosine, histidine and tryptophan
author_facet	Griesbeck, Axel G Neudörfl, Jörg de Kiff, Alan
author_sort	Griesbeck, Axel G
title	Photoinduced electron-transfer chemistry of the bielectrophoric N-phthaloyl derivatives of the amino acids tyrosine, histidine and tryptophan
title_short	Photoinduced electron-transfer chemistry of the bielectrophoric N-phthaloyl derivatives of the amino acids tyrosine, histidine and tryptophan
title_full	Photoinduced electron-transfer chemistry of the bielectrophoric N-phthaloyl derivatives of the amino acids tyrosine, histidine and tryptophan
title_fullStr	Photoinduced electron-transfer chemistry of the bielectrophoric N-phthaloyl derivatives of the amino acids tyrosine, histidine and tryptophan
title_full_unstemmed	Photoinduced electron-transfer chemistry of the bielectrophoric N-phthaloyl derivatives of the amino acids tyrosine, histidine and tryptophan
title_sort	photoinduced electron-transfer chemistry of the bielectrophoric n-phthaloyl derivatives of the amino acids tyrosine, histidine and tryptophan
description	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.
publisher	Beilstein-Institut
publishDate	2011
url	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3107463/
_version_	1611457323678564352

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

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