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Preparation and crystal structure of methyl [12‐acetyl‐8‐ethyl]‐bacteriopheophorbide d. – A new bacteriochlorophyll derivative
Author(s) -
Senge Mathias O.,
Bobe Frank W.,
Huster Michael S.,
Smith Kevin M.
Publication year - 1991
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1991199101150
Subject(s) - chemistry , bacteriochlorophyll , sodium methoxide , tetrahydrofuran , derivative (finance) , crystal structure , methoxide , methyl group , stereochemistry , oxygen , reaction mechanism , photochemistry , medicinal chemistry , methanol , group (periodic table) , organic chemistry , catalysis , solvent , financial economics , economics , pigment
Reaction of methyl bacteriopheophorbide d 2 in tetrahydrofuran with sodium methoxide led to oxidation of the ethyl side chain at position 12 to afford an acetyl group. Experiments with 18 O 2 suggest a mechanism via abstraction of a proton and reaction of the secondary radical formed with molecular oxygen. The implications of this mechanism for the biosynthesis of the bacteriochlorophylls are discussed. The 12‐acetyl compound 3 was investigated by X‐ray crystallography.