Premium
Intramolecular base‐catalysis in the radical‐scavenging reaction by vitamin E derivatives bearing a pyridine moiety
Author(s) -
Nakanishi Ikuo,
Yakumaru Haruko,
Nyui Minako,
Ohkubo Kei,
Matsumoto Kenichiro,
Fukuhara Kiyoshi,
Okuda Haruhiro,
Fukuzumi Shunichi,
Ozawa Toshihiko,
Anzai Kazunori,
Ikota Nobuo
Publication year - 2010
Publication title -
the faseb journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.709
H-Index - 277
eISSN - 1530-6860
pISSN - 0892-6638
DOI - 10.1096/fasebj.24.1_supplement.lb199
Subject(s) - chemistry , moiety , intramolecular force , pyridine , dpph , medicinal chemistry , catalysis , methanol , radical , vitamin , scavenging , organic chemistry , photochemistry , antioxidant , biochemistry
In order to develop effective radioprotectors, we recently synthesized three vitamin E derivatives bearing a pyridine moiety with a linkage of different spacers. All the vitamin E derivatives efficiently scavenged 2,2‐diphenyl‐1‐picrylhydrazyl radical (DPPH • ) in deaerated methanol at 25 °C. The second‐order rate constant for DPPH • ‐scavenging by one of the vitamin E derivatives determined by the stopped‐flow technique is about 3‐fold larger than that by 2,2,5,7,8‐pentamethylchroman‐6‐ol (PMC), a vitamin E model. This suggests that the pyridine moiety may accelerate the reaction by stabilizing the radical cation generated in the electron transfer from the vitamin E derivative to DPPH • .