Alkyl-phenyl cleavage of the lignin model compounds guaiacylglycol and glycerol-?-guaiacyl ether by Phanerochaete chrysosporium

Goldsby, Gwendolyn P.; Enoki, Akio; Gold, Michael H.

doi:10.1007/bf00406157

Cited by 27 publications

(11 citation statements)

References 15 publications

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“…Enoki etal (1980) and Goldsby et al (1980) obtained glycerol-2-guaiacyl ether äs a degradation product of veratrylglycerol-ß-guaiacyl ether and a-deoxyguaiacylglycerol-ß-guaiacyl ether by Phanerochaete chrysosporiwn under the ligninolytic culture condition. However, they did not report the catabolism of glycerol-2-guaiacyl ether.…”

Section: Discussionmentioning

confidence: 98%

Degradation of a Glycerol-2-Aryl Ether, a Catabolic Intermediate of an Arylglycerol-ß-Aryl Ether, byFusarium solaniM—13—1

Katayama¹,

Higuchi²,

Ohura³

et al. 1989

Holzforschung

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Keywords Lignin biodcgradalion Arylglyccrol-ß-aryl ethcrGlyccrol-2-( vanillic acid) cthcr 3-Ethoxy-4-h\ droxybcnzoic acid Vanillic acid Fusarium solani M-13-l Summary Degradation of glyccrol-2-(vanillic acid) cthcr (1) which is a catabolic intcrmcdiatc of guaiacylglycerol-ß-(vanillic acid) cthcr. thc most important lignin substructure model. by Fusarium solani M-13-l was invcstigated. Compound l was complctcly dcgradcd without accumulation of dctcctablc amounts of catabolic products. Thus. dcgradation of glyccrol-2-(3-cthoxy-4-hydroxybenzoic acid) cther (2). which has an cthoxyl group instcad of a mcthoxyl group. by thc fungus was cxamincd. Compound 2 was complctcly degradcd, and 3-cthoxy-4-h v droxybcnzoic acid (3) äs a major catabolic product with two minor catabolic products. 4-hydroxy-3-vinyloxybcn2oic acid (4) and 3,4-(hydroxymethyl)mcthylenedioxybcnzoic acid (5). wcrc isolatcd and idcntificd from thc culturc filtratc. Both compounds 3 and 4 wcrc complctcly dcgradcd, but 5 rcmained in thc culturc in thc constant amount. Thc rcsults indicatcd that thc 2-(ß-) aryl cthcr linkagc of 2 was clcavcd by thc culturc of F. solani M-13-1. It is suggcstcd that l is dcgradcd via thc clcavagc of its 2-(ß-) aryl cthcr bond.

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Section: Discussionmentioning

confidence: 98%

Degradation of a Glycerol-2-Aryl Ether, a Catabolic Intermediate of an Arylglycerol-ß-Aryl Ether, byFusarium solaniM—13—1

Katayama¹,

Higuchi²,

Ohura³

et al. 1989

Holzforschung

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“…Growth was vigorous in all cases. (1980), Goldsby et al (1980) and Shimada et al (1981) found that degradation and metabolism were inhibited. chrysosporium in agitated cul-9 Sk 11 Fig.…”

Section: Discussionmentioning

confidence: 99%

Scanning Electron Microscope Observations of Fungal Associations with Lignin and Insoluble Dimeric Lignin Model Compounds

Betts¹,

Dart²,

Ball³

1987

Holzforschung

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“…The low specificity of the ligninolytic system (Lundquirt et d., 1977;Crawford et al. 1981;Goldsby et al, 1980;Enoki etal.. 1981;Enoki and Gold. 1980;Nakatsubo ct id.. 1981a) also supports the hypothesis that an active oxygen species may be involved.…”

Section: Rwmowci-iol\imentioning

confidence: 99%

Riboflavin‐photosensitized Oxidative Degradation of a Variety of Lignin Model Compounds

Kutsuki¹,

Enoki

Gold³

1983

Photochem & Photobiology

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Oxidation of several lignin model compounds with alkylated paraphenolic groups by photosensitizing riboflavin (RF). rose bengal (RB) and methylene blue (MB) was examined. Photosensitizing RF cleaved l–(3‘‐4’‐diethoxyphenyl)‐1.3 dihydroxy‐2‐(4‐methoxyphenyl)propane (I). 4‐ethoxy‐3‐methoxyphenylglycerol‐(3‐guaiacyl ether (II) and l‐(4‘‐ethoxy‐3’‐methoxyphenyI)‐1,3 dihydroxypropane (IV) at their respective Cα‐Cβ bonds. Riboflavin also oxidized 3.4‐diethoxy‐benzaldehyde (VI) to the corresponding acid, and hydroxylated the conjugated olefin l‐(4‘‐ethoxy‐3’‐methoxyphenyl)1.2 propene (III) to yield the initial product IV. In contrast, MB and RB hydroxylated III but had no effect on I, II, IV or VI under identical conditions. This suggested RF effected transformations via a hydrogen radical abstraction (Type I) rather than a 1O2 mediated reaction. To confirm this, the effects of deuterium oxide (D:0) and oxygen pressure on the photosensitizing dye reactions were examined. The effect of D20 on tryptophan (Trp) oxidation and hydroxylation of III by MB and RB was significant, indicating involvement of 1O2. D2O had no significant effect on cleavage of the diarylpropane (I) and the olefin (III) by RF, indicating these reactions did not proceed by a Type II mechanism. While O2 pressure effect on Trp oxidation by MB was insignificant, it had a large negative effect on cleavage of I by RF. These results, coupled with the relatively slow oxidation rate of Trp by RF. indicate that photosensitizing RF produces 1O2 inefficiently and is not effecting oxidation of these lignin model compounds via a Type II mechanism.

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Alkyl-phenyl cleavage of the lignin model compounds guaiacylglycol and glycerol-?-guaiacyl ether by Phanerochaete chrysosporium

Cited by 27 publications

References 15 publications

Degradation of a Glycerol-2-Aryl Ether, a Catabolic Intermediate of an Arylglycerol-ß-Aryl Ether, byFusarium solaniM—13—1

Degradation of a Glycerol-2-Aryl Ether, a Catabolic Intermediate of an Arylglycerol-ß-Aryl Ether, byFusarium solaniM—13—1

Scanning Electron Microscope Observations of Fungal Associations with Lignin and Insoluble Dimeric Lignin Model Compounds

Riboflavin‐photosensitized Oxidative Degradation of a Variety of Lignin Model Compounds

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