Über Oxo‐porphyrine: Ein Beitrag zur Kenntnis der Feinstruktur von Chlorophyll a

Fischer, Hans; Riedmair, Josef; Hasenkamp, Johann

doi:10.1002/jlac.19345080120

Cited by 21 publications

(7 citation statements)

References 6 publications

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“…4. Ethyl pheophorbide a-oxime: This was prepared according to the method of Fischer et al (2). Fortytwo mg of ethyl pheophorbide a were dissolved in 2.5 ml of pyridine containing 0.33 gm of NH2OH * HCl, and allowed to stand 8 days in darkness at room temperature.…”

Section: H Nmentioning

confidence: 99%

Infra-Red Absorption Spectra of Chlorophylls and Derivatives

Holt¹,

Jacobs²

1955

Plant Physiol.

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We have measured the infra-red absorption spectra of chlorophyll and some of its derivatives in order to obtain information useful for eventual understanding of reversible transformations of this pigment. Such transformations are (a) Moliseh phase test, (b) bleaching by FeCl3, and (c) photochemical reduction by ascorbic acid-"Krasnovsky reaction" (10, 13, 16). Only in the case of the phase test is there evidence of the specific group involved (the cyclopentanone ring). Whether this ring is involved in the other reactions is not known. However, if the C=O bands in the spectrum of the parent substance are correctly assigned, any change in this ring should be apparent from the infra-red spectrum of the intermediate. To obtain unequivocal assignments of the C=O stretching bands we prepared and studied appropriate derivatives. In addition we studied the influence of solvent on the spectrum and found strong effects in the C=O region. These solvent effects were not studied by earlier investigators (18, 19). The complexity of the spectra below 1600 cm-' is so great that we have not attempted to assign the bands. Spectra are presented from 650 to 3800 cm-1 in order to make the data available for future comparisons (except in cases of chlorophyll a in ethyl ether and ethyl pheophorbide a-oxime in CHCl3). MIATERIALS AND METHODS Preparative techniques for most of the pigments studied have been described by us elsewhere (5, 6, 8). Those not described are as follows: 1. Pheophorbide a: Two-tenths gm of pheophytin a were incubated in a mixture of 80 % acetone (v/v, 1

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Section: H Nmentioning

confidence: 99%

Infra-Red Absorption Spectra of Chlorophylls and Derivatives

Holt¹,

Jacobs²

1955

Plant Physiol.

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“…At about the same time H. Fischer and co-workers commenced the publication of their investigations on the chemistry of bacteriochlorophyll, through which not only important details were added, but also misconceptions were cleared up, and ultimately the exact chemical structure of the molecule became fairlywell established (110)(111)(112)(113)(114)(115)(116). Thus they demonstrated the presence of a phytyl group which can be split off by "chlorophyllase," and succeeded in carrying out the degradation of bacteriochlorophyll to oxo-pheoporphyrin a5, the latter a typical derivative of the chlorophyll a series.…”

mentioning

confidence: 99%

The Culture, General Physiology, Morphology, and Classification of the Non-Sulfur Purple and Brown Bacteria

Niel¹

1944

Bacteriological Reviews

234

104

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“…For example, pheoporphyrin a6 (XVI) with iodine in alcohol in the presence of sodium acetate is converted into 10-hydroxypheoporphyrin (or neopheoporphyrin a6). If sodium carbonate is substituted for the acetate, the product is 10-ethoxypheoporphyrin a6 (or pheoporphyrin a6; XXII d) (53). A series of homologous ethers has been prepared by the use of the corresponding series of alcohols in this oxidation (55).…”

Section: Allomerizationmentioning

confidence: 99%

“…Secondly, Fischer found that if his hydrogen iodide reaction was carried out in the cold, instead of at temperatures of 50°or 60°C., a new series of compounds, ketoporphyrins in structure, were obtained (52,53). For instance, chlorophyll a and pheophorbide a both yield oxopheoporphyrin a6, pyropheophorbide yields oxophylloerythrin, chlorin e trimethyl ester yields oxochloroporphyrin eg, while chlorin e yields oxochloroporphyrin e6.…”

Section: The Vinyl Groupmentioning

confidence: 99%

“…The first step would then be the introduction of the carbomethoxyl residue into the isocyclic ring to give pheoporphyrin a6. Fischer could not achieve this, although he found it possible to introduce the ethoxyl residue by the iodine oxidation method, with the formation of 10-ethoxyphylloerythrin (53). Higher homologues were also prepared (55).…”

Section: Chlorophyll Bmentioning

confidence: 99%

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