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Peptide Release upon Photoconversion of 2‐Nitrobenzyl Compounds into Nitroso Derivatives
Author(s) -
Nakayama Koji,
Heise Inge,
Görner Helmut,
Gärtner Wolfgang
Publication year - 2011
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.2011.00957.x
Subject(s) - histidine , chemistry , nitroso , nitro , peptide , amino acid , yield (engineering) , quantum yield , absorption (acoustics) , photochemistry , combinatorial chemistry , organic chemistry , biochemistry , fluorescence , materials science , alkyl , physics , quantum mechanics , metallurgy , composite material
The photoinduced conversion via the aci ‐nitro into the nitroso form was studied for 4,5‐dimethoxy‐2‐nitrobenzyl alcohols attached to various leaving groups: amino acids histidine (NHis) and aspartate (NAsp) as well as their fluorenylmethoxycarbonyl derivatives (FHis) and (FAsp). In addition, two peptides containing either of the two amino acids were studied, carrying the photoreactive group attached to a histidine (PHis), or to an aspartate (PAsp). The aci ‐nitro forms with maximum at λ aci = 420 nm were observed for FHis and FAsp after the decay of a triplet–triplet absorption, analogous to those of other 2‐nitrobenzyl type compounds. For both FHis and FAsp the quantum yield of photoconversion Φ p is 0.03 and for the peptides PHis and PAsp ca 0.01 and 0.005, respectively.