Reductive ipso-radical cyclization onto aromatic rings of five-membered alicyclic amino acids bearing N-(2-phenyl)benzoyl groups by photoinduced electron transfer promoted decarboxylation

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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ChemInform Abstract: Photoinduced Electron Transfer (PET) Promoted Oxidative Activation of 1-(N-Benzyl-N-methylglycyl)-(S)-prolinol: Development of Novel Strategies Towards Enantioselective Syntheses of α-Amino Acids, Their N-Methyl Derivatives, and α-Hyd

ChemInform ◽

10.1002/chin.200018060 ◽

2010 ◽

Vol 31 (18) ◽

pp. no-no

Author(s):

Ganash Pandey ◽

Parthasarathi Das ◽

P. Yella Reddy

Keyword(s):

Amino Acids ◽

Electron Transfer ◽

Photoinduced Electron Transfer ◽

Oxidative Activation ◽

Methyl Derivatives ◽

Enantioselective Syntheses

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Role of the electrostatic energy between the photo-products and ionic groups on the photoinduced electron transfer rates from aromatic amino acids to the excited flavin in five single-point substitution isoforms of the charged amino acid residue-13 in the FMN-binding protein

Molecular Simulation ◽

10.1080/08927022.2014.902534 ◽

2014 ◽

Vol 41 (7) ◽

pp. 580-591 ◽

Cited By ~ 5

Author(s):

Nadtanet Nunthaboot ◽

Kiattisak Lugsanangarm ◽

Arthit Nueangaudom ◽

Somsak Pianwanit ◽

Sirirat Kokpol ◽

...

Keyword(s):

Amino Acids ◽

Electron Transfer ◽

Photoinduced Electron Transfer ◽

Single Point ◽

Aromatic Amino Acids ◽

Electrostatic Energy ◽

Transfer Rates ◽

Ionic Groups ◽

Charged Amino Acid Residue

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Photoinduced electron transfer from amino acids and proteins to 4-nitroquinoline 1-oxide in aqueous solutions

The Journal of Physical Chemistry ◽

10.1021/j100285a038 ◽

1987 ◽

Vol 91 (1) ◽

pp. 176-179 ◽

Cited By ~ 15

Author(s):

Hiroshi. Seki ◽

Akiko. Takematsu ◽

Shigeyoshi. Arai

Keyword(s):

Amino Acids ◽

Electron Transfer ◽

Aqueous Solutions ◽

Photoinduced Electron Transfer

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Decarboxylative radical addition of N-Boc-amino acids to acrylonitrile via photoinduced electron transfer using 1,4-dicyanonaphthalene

Research on Chemical Intermediates ◽

10.1007/s11164-012-0657-z ◽

2012 ◽

Vol 39 (1) ◽

pp. 397-402 ◽

Cited By ~ 8

Author(s):

Yasuharu Yoshimi ◽

Shota Hayashi ◽

Keisuke Nishikawa ◽

Yoshiki Okita ◽

Kousuke Maeda ◽

...

Keyword(s):

Amino Acids ◽

Electron Transfer ◽

Photoinduced Electron Transfer ◽

Radical Addition

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ChemInform Abstract: Photoreaction of Halomethyl Substituted Benzocyclic Ketones with Amines: Radical Cyclization and Ring Expansion Reactions Promoted Through Photoinduced Electron-Transfer Processes.

ChemInform ◽

10.1002/chin.199805045 ◽

2010 ◽

Vol 29 (5) ◽

pp. no-no

Author(s):

E. HASEGAWA ◽

Y. TAMURA ◽

E. TOSAKA

Keyword(s):

Electron Transfer ◽

Photoinduced Electron Transfer ◽

Ring Expansion ◽

Radical Cyclization ◽

Transfer Processes ◽

Electron Transfer Processes

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Classification of the mechanisms of photoinduced electron transfer from aromatic amino acids to the excited flavins in flavoproteins

Physical Chemistry Chemical Physics ◽

10.1039/c5cp01432h ◽

2015 ◽

Vol 17 (26) ◽

pp. 16813-16825 ◽

Cited By ~ 3

Author(s):

Fumio Tanaka ◽

Kiattisak Lugsanangarm ◽

Nadtanet Nunthaboot ◽

Arthit Nueangaudom ◽

Somsak Pianwanit ◽

...

Keyword(s):

Amino Acids ◽

Electron Transfer ◽

Photoinduced Electron Transfer ◽

Aromatic Amino Acids ◽

Wavelength Dependence ◽

Emission Wavelength ◽

Donor Acceptor ◽

The Relationship

Emission wavelength-dependence of the relationship between logarithmic ET rate vs. donor–acceptor distance in pyranose 2-oxidase.

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Photoinduced electron transfer from aromatic amino acids to the excited isoalloxazine in flavin mononucleotide binding protein. Is the rate in the inverted region of donor–acceptor distance not real?

Journal of Photochemistry and Photobiology A Chemistry ◽

10.1016/j.jphotochem.2016.04.005 ◽

2016 ◽

Vol 326 ◽

pp. 60-68 ◽

Cited By ~ 9

Author(s):

Nadtanet Nunthaboot ◽

Kiattisak Lugsanangarm ◽

Arthit Nueangaudom ◽

Somsak Pianwanit ◽

Sirirat Kokpol ◽

...

Keyword(s):

Amino Acids ◽

Electron Transfer ◽

Photoinduced Electron Transfer ◽

Binding Protein ◽

Aromatic Amino Acids ◽

Flavin Mononucleotide ◽

Inverted Region ◽

Donor Acceptor

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Photoinduced electron transfer in Nano-Saturn complexes of fullerene

Physical Chemistry Chemical Physics ◽

10.1039/d0cp05919f ◽

2020 ◽

Author(s):

Olga A. Stasyuk ◽

Anton J Stasyuk ◽

Miquel Solà ◽

Alexander Voityuk

Keyword(s):

Electron Transfer ◽

Inclusion Complexes ◽

Photoinduced Electron Transfer ◽

Aromatic Rings ◽

Shaped Inclusion

The photoinduced electron transfer is studied computationally in several Saturn-shaped inclusion complexes of carbo-aromatic rings and C60 fullerene – C72⊃C60, C96⊃C60, C120⊃C60, and C168⊃C60. Analysis of their structural and electronic...

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