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- W2002045900 abstract "Chromsäureoxidation des natürlichen Gemisches der Bacteriophäophorbid-d-methylester 1 aus Chlorobium vibrioforme liefert neben den Maleinimiden 3a, 3b, 3c und (2S,3S)-Dihydrohämatin-säureimid-methylester, der mit einer authentischen Probe von 2 identifiziert wurde. Wird das aus 1 leicht zugängliche 131-Desoxoderivat 4c dem oxidativen Abbau unterworfen, so entstehen aus Ring C der Phäophorbide zusätzlich die Imide 6a und 6b, wodurch die Art der C-12 Substituenten von 1 bewiesen ist. Schließlich läßt sich auch Ring A des Chromophors in Form des Abbau-imids 8 isolieren, wenn vor der Oxidation die 31-Hydroxygruppe von 1 benzoyliert wird. Aus 8 entsteht bei der Ozonolyse (R)-Benzoylmilchsäure, ein Beweis für die (31R)-Konfiguration der Bacteriochlorophylle d. Absolute Configuration of Chlorophylls, IX. — Oxidative Degradation of Bacteriochlorophyll d, Confirmation of the Structure and Determination of the Absolute Configuration Chromic acid oxidation of the naturally occurring mixture of bacteriophaephorbide d methyl esters 1 from Chlorobium vibrioforme yields the maleimides 3a, 3b, 3c and the methyl ester of (2S,3S)-dihydrohaematinimide which was identified with an authentic sample of 2. By oxidative degradation of the 131-deoxo compound 4c, which is easily accessible by reduction of 1, in addition to 2 and 3 the imides 6a and 6b are obtained from ring C of the phaeophorbide. Thus the nature of the C-12 substituent is proven. Finally also ring A of the chromophore can be isolated as the imide 8, if the 31-hydroxy group of 1 is benzoylated prior to oxidation. (R)-Benzoyllactic acid, obtained by ozonolysis of 8, proves the (31R)-configuration of bacteriochlorophylls d." @default.
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- W2002045900 date "1979-03-26" @default.
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- W2002045900 title "Zur absoluten Konfiguration der Chlorophylle, IX Oxidativer Abbau von Bacteriochlorophyll d, Bestätigung der Konstitution und Bestimmung der absoluten Konfiguration" @default.
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- W2002045900 doi "https://doi.org/10.1002/jlac.197919790314" @default.
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