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  • 1
    ISSN: 1520-5835
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology , Physics
    Type of Medium: Electronic Resource
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  • 2
    ISSN: 1432-072X
    Keywords: Lignin blodegradation ; Phenylcoumaran ; Phanerochaete chrysosporium ; Propiosyringone derivative ; Phenylcoumarones ; Syringic acid ; 2,6-Dimethoxy-p-benzoquinone ; 5-Carboxyvanillic acid
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract The degradation of a lignin substructure model compound, 5-formyl-3-hydroxymethyl-2-(4-hydroxy-3,5-dimethoxyphenyl)-7-methoxycoumaran (I), in ligninolytic culture of a white-rot wood decay fungus,Phanerochaete chrysosporium, was investigated. It was found that I was hydroxylated or dehydrogenated in its coumaran ring to give 2-(5-formyl-2-hydroxy-3-methoxyphenyl)-3-hydroxypropiosyringone (II) and two coumarones, 5-formyl-3-hydroxymethyl-2-(4-hydroxy-3,5-dimethyoxyphenyl)-7-methoxycoumarone (V) and 3,5-diformyl-2-(4-hydroxy-3,5-dimethoxyphenyl)-7-methoxycoumarone (VI), II was further converted to 2,6-dimethoxy-p-benzoquinone (IV), syringic acid (III), and 5-carboxyvanillic acid (VIII). These metabolic products were identified by mass spectrometric comparison with the authentic compounds. A proposed pathway for the degradation of I is presented on the basis of these metabolic products. The degradation could be catalyzed mainly by phenol-oxidizing enzymes.
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  • 3
    ISSN: 1432-072X
    Keywords: Lignin biodegradation ; Fusarium solani ; d,l-Syringaresinol ; Alkyl-aryl cleavage ; 2,6-Dimethoxy-p-benzoquinone
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract A β-β′ linked lignin model compound, d,l-syringaresinol monobenzyl ether (Ib) was incubated with Fusarium solani M-13-1 in a shaking culture. From the culture filtrates, three compounds II, IIIb and IV were isolated and identified. Substrate Ib was oxidized at the α-position of the side chain to give a hemiketal, an α-hydroxylated compound IIA, which was then transformed to the ketoalcohol, 3-hydroxymethyl-2-(4-benzyloxy-3,5-dimethoxyphenyl)-4-(4-hydroxy-3,5-dimethoxybenzoyl)-tetrahydrofuran (IIB). These products were converted to a γ-lactone derivative, 6-oxo-2-(4-benzyloxy-3,5-dimethoxyphenyl)-3,7-dioxabicyclo-[3,3,0]-octane (IIIb), via alkyl-aryl cleavage. The syringyl moiety released from II by the cleavage reaction was identified as 2,6-dimethoxy-p-benzoquinone (IV). Incubation of 2,6-dimethoxyphenol (V) in fungal culures did not give the p-quinone IV. d,l-Syringaresinol dimethyl ether was not degraded and the etherated moiety of Ib was not attacked by the fungus, indicating that the degradation of d,l-syringaresinol was catalyzed by phenol oxidizing enzymes. The oxidation products of Ib with peroxidase/H2O2 was investigated and discussed in relation to the degradation products of the fungus.
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  • 4
    ISSN: 1432-072X
    Keywords: White-rot fungi ; Secondary metabolism ; Wood decay ; Mycelial pellets ; Fungus physiology ; l-Glutamic acid repression ; Phenylalanine
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract The lignin-degrading basidiomycete Phanerochaete chrysosporium synthesizes veratryl alcohol (3,4-dimethoxybenzyl alcohol) via phenylalanine, 3,4-dimethoxycinnamyl alcohol and veratrylglycerol. Study of the conversion of 3,4-dimethoxycinnamyl alcohol to veratrylglycerol and veratryl alcohol showed is to be (a) catalyzed by a secondary metabolic system, (b) markedly suppressed by culture agitation, and (c) strongly inhibited by l-glutamate. The amount of veratryl alcohol synthesized de novo was positively correlated with the O2 concentration after primary growth. Other work has shown that the cinnamyl alcohol terminal residue in a lignin substructure model compound is degraded via arylglycerol and benzyl alcohol structures in ligninolytic cultures of P. chrysosporium, and that the ligninolytic system exhibits traits (a)-(c) above. Ligninolytic activity is also strongly and positively correlated with O2 concentration. The results here suggest, therefore, that the actual biosynthetic secondary metabolic product is 3,4-dimethoxycinnamyl alcohol, but that this is degraded by the ligninolytic system to veratryl alcohol via veratrylglycerol. Veratryl alcohol is only slowly metabolized by the fungus, and accumulates.
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  • 5
    Electronic Resource
    Electronic Resource
    Springer
    Archives of microbiology 130 (1981), S. 198-203 
    ISSN: 1432-072X
    Keywords: Lignin biodegradation ; Arylglycerol-β-aryl ether ; Fusarium solani ; Alkyl-aryl cleavage ; Phenol oxidizing enzymes ; Glycerol-2-vanillic acid ether ; 2,6-Dimethoxy-p-benzoquinone
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract Degradation of arylglycerol-β-aryl ethers, the most important substructure in lignin, by Fusarium solani M-13-1 was investigated. The fungus was shake-cultured in mineral salts media which contained either guaiacylglycerol-β-vanillic acid ether (2), syringylglycerol-β-vanillin ether (4), veratrylglycerolβ-vanillin ether (17) or glycerol-2-vanillic acid ether (9) as sole carbon source. Culture filtrates from incubations with 4 contained syringylglycerolβ-vanillic acid ether (6), 9 and 2,6-dimethoxy-p-benzoquinone (16). Culture filtrates from incubations with 2 also contained 9. Veratrylglycerol-β-vanillic acid ether (18) derived from 17 was not metabolized further. These results inidicate that the alkyl-aryl C-C bond in both 2 and 5 was cleaved by phenol oxidizing enzymes with formation of 9 and methoxy-p-benzoquinone (15 and 16). Compound 9 was converted to glycerol-2-vanillic acid ether monoacetate (10), glyceric acid-2-vanillic acid ether (11) and ethylene glycol monovanillic acid ether (12).
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  • 6
    ISSN: 1432-072X
    Keywords: Guaiacylglycerol-β-coniferyl ether ; Lignin biodegradation ; Fusarium solani ; Guaiacylglycerol-β-coniferyl aldehyde ether ; Guaiacylglycerol-β-ferulic acid ether ; Guaiacylglycerol-β-vanillin ether ; Guaiacylglycerol-β-vanillic acid ehter ; erythro form ; threo form
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract Fusarium solani M-13-1 was shake-cultured in a medium containing guaiacylglycerol-β-coniferyl ether (I), a model compound representing the arylglycerol-β-aryl ether linkage in lignin, as sole carbon source. From the culture filtrate guaiacylglycerol-β-coniferyl aldehyde ether (II) and guaiacylglycerol-β-ferulic acid ether (III) were isolated as metabolic products. Incubation with (III) resulted in formation of guaiacylglycerol-β-vanillin ether (IV), which was further metabolized to guaiacyglycerol-β-vanillic acid ether (V). The results indicate that the cinnamyl alcohol group of (I) is initially oxidized to an aldehyde group, which is further oxidized to a carboxyl group, yielding (II) and (III). Compound (III) is converted to (IV) by the release of a C2 fragment, and the aldehyde group of (IV) is further oxidized to a carboxyl group, giving (V). In the pathway from (I) to (V), neither oxidation of the benzylic secondary alcohol to ketone nor cleavage of the arylglycerol-β-aryl ether linkage was observed. The fungus was found to attack both erythro and threo form without distinction.
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  • 7
    ISSN: 1432-072X
    Keywords: Lignin biodegradation ; White-rot fungi ; Fungus physiology ; Wood decay ; Aromatic metabolism ; Phanerochaete chrysosporium
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract The degradation of the phenylcoumaran substructure model compound methyl dehydrodiconiferyl alcohol by the white-rot wood decay fungus Phanerochaete chrysosporium was investigated using culture conditions optimized for lignin oxidation. Initial attack was in the cinnamyl alcohol side chain, which was oxidized to a glycerol structure. This was subsequently converted by loss of the two terminal carbon atoms, Cβ′ and Cγ′, to yield a Cα′-aldehyde structure, which was further oxidized to the Cα′-acid compound. The next detected intermediate, a phenylcoumarone, was produced by double bond formation between Cα and Cβ, and oxidation of the Cγ-alcohol to an aldehyde group. Further oxidation of Cγ to an acid yielded the next intermediate. The final identified degradation product was veratric acid. No products from the 5-substituted aromatic ring, and no phenolic products, were found. The initial glycerol-containing intermediate was a mixture of the threo and erythro forms, and no optical activity could be found, suggesting that its formation might have involved nonstereospecific Cα′-Cβ′ epoxidation followed by non-enzymatic hydrolysis of the epoxide.
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  • 8
    ISSN: 1572-882X
    Keywords: cellulose-homologous series ; chemical synthesis ; gelpermeati on chromatography ; molecular rotation ; regio-selectivelysubstituted cellulose
    Source: Springer Online Journal Archives 1860-2000
    Topics: Agriculture, Forestry, Horticulture, Fishery, Domestic Science, Nutrition , Process Engineering, Biotechnology, Nutrition Technology
    Notes: Abstract Two homologous series of regio- selectively sub stituted cellulose: 3-O-benzyl-2, 6-di-O-pivaloyl derivatives (Series 1) and 2,3,6-tri-O-acetyl derivatives (Series 2) up to an eicosamer (DP = 20), were synthesized for the first time by elongation of the carbohydrate chain from cellooctaose derivative 5 and subsequent deprotection. Some changing properties of the homologous series with increasing DP were examined. Gel permeation chromatography (GPC) analysis for series 1 and 2 indicated that plots of log M vs retention time gave a straight line. The plots of [M]n/n vs (n − 1)/n (where [M]n is the molecular rotation for an oligomer with DP = n) up to a hexadecamer 9 in series 2 gave straight lines, although the result for the eicosamer 11 deviated somewhat from the line
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  • 9
    ISSN: 1611-4663
    Keywords: Hematoxylin ; Impregnation ; Vibrational property ; Dimensional stability ; Extractive
    Source: Springer Online Journal Archives 1860-2000
    Topics: Agriculture, Forestry, Horticulture, Fishery, Domestic Science, Nutrition , Mechanical Engineering, Materials Science, Production Engineering, Mining and Metallurgy, Traffic Engineering, Precision Mechanics
    Notes: Abstract The impregnation of various simple phenolic and natural polycyclic compounds into wood was investigated from the viewpoints of vibrational property and dimensional stabilizing effect. When simple phenolic compounds were impregnated, the loss tangent (tan δ) in the longitudinal direction increased linearly with increasing weight gain. Meanwhile, among the natural polycyclic compounds hematoxylin decreased the tan δ drastically by impregnation. It was suggested that the five hydroxyl groups and the pyran ring oxygen in the hematoxylin molecule contribute to formation of the crosslinkage-type hydrogen bonds between wood components. The rigidity of hematoxylin molecules may also be important. By impregnation of about 10% catechol, resorcinol, and saligenin, a 40% level of antiswelling efficiency (ASE) was attained, although a significant dimensional stabilizing effect was not observed after impregnation of natural polycyclic compounds.
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  • 10
    ISSN: 1611-4663
    Keywords: Pernambuco ; Vibrational property ; Extractives ; Impregnation ; Musical instrument
    Source: Springer Online Journal Archives 1860-2000
    Topics: Agriculture, Forestry, Horticulture, Fishery, Domestic Science, Nutrition , Mechanical Engineering, Materials Science, Production Engineering, Mining and Metallurgy, Traffic Engineering, Precision Mechanics
    Notes: Abstract Sitka spruce (Picea sitchensis Carr.) was treated with water-soluble extractive components of pernambuco (Guilandina echinata Spreng. syn Caesalpinia echinata Lam.) by two methods: impregnation under evacuation using an aspirator and repetitive surface application using a brush. The influence of these treatments on the vibrational properties were examined. The loss tangent (tan δ) of the impregnated specimen decreased, up to nearly a half of its original value, with increasing weight gain. It is suggested that the decrease in tan δ results from impregnation of the extractive components into the amorphous region of cell walls, forming secondary bonds between matrix substances. The surface application of the extractive components, on the other hand, hardly brought about the desirable change in vibrational properties.
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