Self-aggregation of synthetic bacteriochlorophyll-d analogues possessing a B-ring reduced chlorin pi-system.
Zinc 3(1)-hydroxy-13(1)-oxo-chlorophyll derivatives 3 and 4 having a B-ring reduced chlorin pi-system (C7-C8, C17=C18) were prepared as models of self-aggregative bacteriochlorophyll-d, which are regioisomers of 1 and 2 possessing a natural-type D-ring reduced chlorin pi-system (C7=C8, C17-C18). 3(1)-Epimerically pure forms of secondary alcohol 3 (3-CH(OH)CH(3)) as well as primary alcohol 4 (3-CH(2)OH) were effectively synthesized by modifying naturally available bacteriochlorophyll-a. Self-aggregation of 3 and 4 in an aqueous micellar solution was examined by UV-vis and CD spectroscopies and compared with that of their regioisomeric 1 and 2.
Department of Bioscience and Biotechnology, Faculty of Science and Engineering, Ritsumeikan University, Kusatsu, Shiga 525-8577, Japan.
Michio
M
Kunieda
Hitoshi
H
Tamiaki
D001429:Bacteriochlorophylls / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011166:Porphyrins / Q000737:chemistry*; D016339:Spectrometry, Mass, Fast Atom Bombardment
D001429:Bacteriochlorophylls; D011166:Porphyrins; C006969:chlorin; C459779:bacteriochlorophyll d