101908-72-9Relevant academic research and scientific papers
COENZYME MODELS. PART 45. SYNTHESIS OF ATROPISOMERIC FLAVINS AND THEIR NOVEL REDOX-INDUCED RACEMISATION
Shinkai, Seiji,Nakao, Hideki,Kuwahara, Itsuko,Miyamoto, Megumi,Yamaguchi, Toshiro,Manabe, Osamu
, p. 313 - 320 (2007/10/02)
Seven (5-carba)isoalloxazines with restricted rotation about the C(1')-N(10) single bond were synthesized for the first time.They were optically resolved by a liquid chromatographic method.Six of these atropisomers (92.1-100 percent enantiomeric excess) (
Novel Racemization of Atropisomeric Flavins and 5-Deazaflavins via Adduct Formation
Shinkai, Seiji,Nakao, Hideki,Yamaguchi, Toshiro,Manabe, Osamu
, p. 307 - 309 (2007/10/02)
The molecular structures of covalent adducts derived from flavins and 5-deazaflavins are discussed on the basis of racemization of atropisomeric flavins and 5-deazaflavins.The 5-adducts with SO32- and CN- underwent facile racemization, indicating that the molecular structure changes from the "tense" planar state to the "relaxed" bent state.On the other hand, the 4a-adduct prepared by the photo-alkylation method did not racemize at room temperature. this indicates that the structure of the 4a-adduct is different from the bent 5-adduct. these results provide an information useful to discuss the reduced state of flavoproteins.
SYNTHESIS AND OPTICAL RESOLUTION OF A NEW FLAVIN WITH AXIAL CHIRALITY AND REDOX-DEPENDENT RACEMIZATION
Shinkai, Seiji,Nakao, Hideki,Manabe, Osamu
, p. 5183 - 5186 (2007/10/02)
A new flavin (3-methyl-10-(2'-phenyl)phenylisoalloxazine) with restricted rotation about the C(1')-N(10) single bond was synthesized and optically resoluted for the first time. (+)-Isomer (100percent enantiomeric purity) did not racemize at ambient condit
