Chlorophylls. IV. Preparation and Purification of Some Derivatives of Chlorophylls a and b.

Hynninen, Paavo H.; Jakobsen, Palle; Ruiz, María Esther; Waisvisz, Jacques M.; Hoeven, Marcel G. van der; Swahn, Carl‐Gunnar

doi:10.3891/acta.chem.scand.27-1771

Cited by 67 publications

(33 citation statements)

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“…We prepared semisynthetic chlorophyll derivative 1 from pyropheophorbide a methyl ester by using classic methods in acidic hydrolysis of the propionic acid methyl ester [13] and zinc insertion. [14] The characteristics of the formation of the complex between Zn pyropheophorbide a (1) and nicotine (2) was studied by NMR spectroscopy in CDCl 3 .…”

Section: Resultsmentioning

confidence: 99%

Zn Pyropheophorbide a: A β‐Face Selective Nicotine Receptor

2008

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Nicotine binds to a semisynthetic chlorophyll a derivative, Zn pyropheophorbide a, in a receptor‐like manner to form a 1:1 complex with β‐face diastereomeric configuration. The geometry of the complex structure was evidenced by 1H NMR, ROESY and DOSY spectroscopic experiments combined with molecular modelling DFT B3LYP calculations at the 6‐31G* level. The observed binding between the chlorin and nicotine takes place through a “two‐point binding” mechanism, in which the nicotine N‐pyridyl moiety coordinates to the chlorin zinc atom, whilst the nicotine N‐methyl pyrrolidine unit forms an ion pair with the chlorin acid group. The binding mechanism was further confirmed by association constants (Ka) obtained from titration experiments in CDCl3 with 1H NMR spectroscopic monitoring (8.0 × 105 M–1) and in toluene with UV/Vis (6.1 × 104 M–1) monitoring. The corresponding binding constants obtained for nicotine with one‐point binder, Zn pyropheophorbide a methyl ester, were 4.8 × 105 and 2.3 × 104 M–1, respectively. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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Section: Resultsmentioning

confidence: 99%

Zn Pyropheophorbide a: A β‐Face Selective Nicotine Receptor

2008

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“…Chl c (c 1 and c 2 mixture) was extracted from the thalli of Undaria pinnatifida. Pheophytins a/c, Pheid b, and bacterio-Pheid a were prepared by acid treatment of pure respective Chls, according to the method of Perkins and Roberts (1962) and Hynninen (1973).…”

Section: Preparation Of Chl Derivativesmentioning

confidence: 99%

Characterization and Cloning of the Chlorophyll-Degrading Enzyme Pheophorbidase from Cotyledons of Radish

2005

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Enzymatic removal of the methoxycarbonyl group of pheophorbide (Pheid) a in chlorophyll degradation was investigated in cotyledons of radish (Raphanus sativus). The enzyme pheophorbidase (PPD) catalyzes the conversion of Pheid a to a precursor of pyropheophorbide (PyroPheid), C-13 2 -carboxylPyroPheid a, by demethylation, and then the precursor is decarboxylated nonenzymatically to yield PyroPheid a. PPD activity sharply increased with the progression of senescence in radish, suggesting de novo synthesis of PPD. The enzyme activity was separated into two peaks in anion-exchange and hydrophobic chromatography; the terms type 1 and type 2 were applied according to the order of elution of these enzymes in anion-exchange chromatography. PPD types 1 and 2 were purified 9,999-and 6,476-fold, with a yield of 0.703% and 2.73%, respectively. Among 12 substrates tested, both enzymes were extremely specific for Pheids of the dihydroporphyrin and tetrahydroporphyrin types, indicating that they are responsible for the formation of these PyroPheids. Both PPDs had molecular masses of 113,000 kD on gel filtration and showed three bands of 16.8, 15.9, and 11.8 kD by SDS-PAGE. The partial N-terminal amino acid sequences for these bands of PPD (type 2) were determined. Based on their N-terminal amino acid sequences, a full-length cDNA of PPD was cloned. The molecular structure of PPD, particularly the molecular mass and subunit structure, is discussed in relation to the results of SDS-PAGE.

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“…Pheophorbides-a and -b were prepared from purified ptns-a and -b by shaking an acetone solution of the appropriate pheophytin with an equal volume of concentrated HCl for 15 minute (Hynninen, 1973). The mixture was then allowed to stand 15 minute Distilled water and CH2C12 were added to the acid solution.…”

Section: Preparation Of Pheqphorbides-a and -Bmentioning

confidence: 99%

“…Pheophytins-a and -b were prepared from crude chls-a and -b by shaking an ether solution of the appropriate chlorophyll with an equal volume of IN HCl for 15 minutes (Hynninen, 1973). A noticeable color change, from green to brown, signified that demetallation had occurred.…”

Section: Preparation Of Phrophytins-a and -Bmentioning

confidence: 99%

Chlorophyll diagenesis in the water column and sediments of the Black Sea

King¹

1992

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This thesis examines the degradation pathways of chlorophyll in the Black Sea water column and sediments. Measurements are made of total chlorophyll in sediment traps from two locations and depths in the water column, and at two locations in surface sediments. Individual chlorophyll degradation products are also identified. This data is used to construct a mass balance of chlorophyll production and sedimentation showing the major pathways for chlorophyll loss and the ultimate sedimentary sinks. The distribution of chlorophyll degradation products is also analyzed down core and related to environmental changes in the Black Sea Several new sinks for chlorophyll degradation products are identified. Steryl esters of pyropheophorbide-a are identified in sediment trap and sediment samples. It is thought that these compounds are formed during grazing. In sediment traps it is found that the distribution of the sterols esterified to pyropheophorbide-a change with season and that the sterols esterified are related to the distribution of sterols synthesized by the phytoplankton living in the photic zone at the time of production. Analysis of pyropheophorbide-a steryl esters in sediments shows the distribution of sterols to be quantitatively and qualitatively more similar to the distribution of free sterols in sediment traps than in sediments. The esterification of the sterols to pyropheophorbide-a apparently prevents the preferential removal of 4-desmethylsterols relative to 4-methylsterols during degradation of the sterol esters.Chlorophyll degradation products which are incorporated into high molecular weight material and material which is only accessible with strong acid are also identified. The chlorophyll degradation products incorporated into these structures represent only a few percent of the total structure. In the high molecular weight material, only phorbins derived from chlorophyll-a are identifies, where as in the acid extractable material, porphyrins are also identified. In surface sediments, the acid extractable chlorophyll degradations products and the solvent extractable macromolecular chlorophyll degradation products each comprise approximately 30% of total sedimentary chlorophyll degradation products. The acid extractable chlorophyll degradation products are identified in sediment trap samples, and evidence is presented for the occurrence of the solvent extractable macromolecular chlorophyll degradation products in sediment trap samples.U sing data from sediment traps, sediments, and the literature, a mass balance of chlorophyll flux, degradation, and accumulation in the Black Sea is presented. In the photic zone, chlorophyll degradation products are either destroyed by photo-oxidation and grazing, or they are transported into the anoxic water column in large, rapidly sinking particles. Once the chlorophyll degradation products have reached the anoxic water column, they survive to be deposited in the underlying sediments. As a comparison, 25 times more total organic carbon reaches the anoxic wate...

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Chlorophylls. IV. Preparation and Purification of Some Derivatives of Chlorophylls a and b.

Cited by 67 publications

References 0 publications

Zn Pyropheophorbide a: A β‐Face Selective Nicotine Receptor

Zn Pyropheophorbide a: A β‐Face Selective Nicotine Receptor

Characterization and Cloning of the Chlorophyll-Degrading Enzyme Pheophorbidase from Cotyledons of Radish

Chlorophyll diagenesis in the water column and sediments of the Black Sea

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