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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Autores principales: Griesbeck, Axel G, Neudörfl, Jörg, de Kiff, Alan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2011
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3107463/
https://www.ncbi.nlm.nih.gov/pubmed/21647325
http://dx.doi.org/10.3762/bjoc.7.60
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author Griesbeck, Axel G
Neudörfl, Jörg
de Kiff, Alan
author_facet Griesbeck, Axel G
Neudörfl, Jörg
de Kiff, Alan
author_sort Griesbeck, Axel G
collection PubMed
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.
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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 Beilstein J Org Chem 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. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://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: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
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
title 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_short 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
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3107463/
https://www.ncbi.nlm.nih.gov/pubmed/21647325
http://dx.doi.org/10.3762/bjoc.7.60
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