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Pyridinio‐isoalloxazinophanes as Model Systems for Active‐Site Complexes in Flavoenzymes: Syntheses, X‐Ray Structure Analyses and Spectroscopic Properties
Author(s) -
Staab Heinz A.,
Zipplies Matthias F.,
Müller Thomas,
Storch Matthias,
Krieger Claus
Publication year - 1994
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19941270918
Subject(s) - chemistry , intramolecular force , cyclophane , stereochemistry , flavin group , x ray , crystallography , organic chemistry , crystal structure , enzyme , physics , quantum mechanics
As model systems for active site complexes in flavoenzymes, flavin and nicotinamide analogues were linked together in cyclophane skeletons of specific sterical structures. Elaborating this concept, we prepared [4]metacyclo[3](10,6)isoalloxazinophane ( 3 ), [4](3,1)pyridino[3](10,6)isoalloxazinophane ( 4 ), as well as the 16‐methoxycarbonyl and the 16‐carboxylato derivatives ( 2 and 34 , resp.), of 4 by multistep syntheses. For the isoalloxazinophanes 2 , 3 , 4 , and 34 X‐ray structure analyses were performed and are discussed with regard to intramolecular interactions. Preliminary UV/Vis‐spectroscopic results related to π…π interactions in these isoalloxazinophanes are reported.