Syntheses of (1,2-13C), (1-13C) and (3-13C) Coniferyl Alcohol

Newman, Joseph P.; Rej, Radindra N.; Just, George; Lewis, Norman

doi:10.1515/hfsg.1986.40.6.369

Cited by 22 publications

(11 citation statements)

References 12 publications

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“…The model contained approximately 0.9 ␤-O-4 dimer per 8,000-average-MW PEG chain. Its specific activity was 1.0 ϫ 10 Ϫ5 mCi mg of total polymer Ϫ1 and 0.1 mCi mmol of attached (25,36), and exhaustively methylated, ␤-14 C-labeled, synthetic guaiacyl lignin (0.01 mCi mmol of phenylpropane substructures Ϫ1 ) (8,16) were prepared by minor modifications of the methods described in the references cited.…”

Section: Methodsmentioning

confidence: 99%

Manganese-Dependent Cleavage of Nonphenolic Lignin Structures by Ceriporiopsis subvermispora in the Absence of Lignin Peroxidase

Jensen¹,

Bao²,

Kawai³

et al. 1996

Appl Environ Microbiol

112

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Many ligninolytic fungi appear to lack lignin peroxidase (LiP), the enzyme generally thought to cleave the major, recalcitrant, nonphenolic structures in lignin. At least one such fungus, Ceriporiopsis subvermispora, is nevertheless able to degrade these nonphenolic structures. Experiments showed that wood block cultures and defined liquid medium cultures of C. subvermispora rapidly depolymerized and mineralized a 14 C-labeled, polyethylene glycol-linked, high-molecular-weight ␤-O-4 lignin model compound (model I) that represents the major nonphenolic structure of lignin. The fungus cleaved model I between C ␣ and C ␤ to release benzylic fragments, which were shown in isotope trapping experiments to be major products of model I metabolism. The C ␣-C ␤ cleavage of ␤-O-4 lignin structures to release benzylic fragments is characteristic of LiP catalysis, but assays of C. subvermispora liquid cultures that were metabolizing model I confirmed that the fungus produced no detectable LiP activity. Three results pointed, instead, to the participation of a different enzyme, manganese peroxidase (MnP), in the degradation of nonphenolic lignin structures by C. subvermispora. (i) The degradation of model I and of exhaustively methylated (nonphenolic), 14 C-labeled, synthetic lignin by the fungus in liquid cultures was almost completely inhibited when the Mn concentration of the medium was decreased from 35 M to approximately 5 M. (ii) The fungus degraded model I and methylated lignin significantly faster in the presence of Tween 80, a source of unsaturated fatty acids, than it did in the presence of Tween 20, which contains only saturated fatty acids. Previous work has shown that nonphenolic lignin structures are degraded during the MnP-mediated peroxidation of unsaturated lipids. (iii) In experiments with MnP, Mn(II), and unsaturated lipid in vitro, this system mimicked intact C. subvermispora cultures in that it cleaved nonphenolic ␤-O-4 lignin model compounds between C ␣ and C ␤ to release a benzylic fragment.

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Section: Methodsmentioning

confidence: 99%

Manganese-Dependent Cleavage of Nonphenolic Lignin Structures by Ceriporiopsis subvermispora in the Absence of Lignin Peroxidase

Jensen¹,

Bao²,

Kawai³

et al. 1996

Appl Environ Microbiol

112

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“…They provide 100% E-configured acrylates when they react with linear aldehydes, and (E)-alkenes 112 , as well as diverse structures like (R)-(À)-[1; 7-13 C 2 ]shikimic acid 67d , [ 13 C]coniferyl alcohol 113 and [ 13 C]valine 66d . The carbanions, generated by a suitable base, are more nucleophilic than the latter, so that they react even with ketones.…”

Section: Replacement Of Halogen With Phosphorus Nucleophilesmentioning

confidence: 99%

Preparation of Carbon‐14‐Labeled Compounds via Multi‐Carbon Building Blocks of the [ ¹⁴ C]Carbon Dioxide Tree

Voges¹,

Heys

Moenius

2009

Preparation of Compounds Labeled With Tritium and Carbon‐14

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“…The phenol in 5 was first protected as its ethoxyethylidene derivative. 11 Compound 5 (1.21 g, 5.87 mmol) and a catalytic amount of pyridinium toluene-p-sulfonate were dissolved in dichloromethane, and then ethyl vinyl ether (1.8 mL, 18.8 mmol) was added. The mixture was stirred at room temperature for 4 h, after which time TLC indicated that the reaction was complete.…”

Section: Synthesis Of Labeled Coniferyl Alcohol 1amentioning

confidence: 99%

Preparation of synthetic lignins with superior NMR characteristics via isotopically labeled monolignols

Ralph¹,

Zhang²,

Ede³

1998

J. Chem. Soc., Perkin Trans. 1

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Syntheses of (1,2-¹³C), (1-¹³C) and (3-¹³C) Coniferyl Alcohol

Cited by 22 publications

References 12 publications

Manganese-Dependent Cleavage of Nonphenolic Lignin Structures by Ceriporiopsis subvermispora in the Absence of Lignin Peroxidase

Manganese-Dependent Cleavage of Nonphenolic Lignin Structures by Ceriporiopsis subvermispora in the Absence of Lignin Peroxidase

Preparation of Carbon‐14‐Labeled Compounds via Multi‐Carbon Building Blocks of the [ ¹⁴ C]Carbon Dioxide Tree

Preparation of synthetic lignins with superior NMR characteristics via isotopically labeled monolignols

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Syntheses of (1,2-13C), (1-13C) and (3-13C) Coniferyl Alcohol

Cited by 22 publications

References 12 publications

Manganese-Dependent Cleavage of Nonphenolic Lignin Structures by Ceriporiopsis subvermispora in the Absence of Lignin Peroxidase

Manganese-Dependent Cleavage of Nonphenolic Lignin Structures by Ceriporiopsis subvermispora in the Absence of Lignin Peroxidase

Preparation of Carbon‐14‐Labeled Compounds via Multi‐Carbon Building Blocks of the [ 14 C]Carbon Dioxide Tree

Preparation of synthetic lignins with superior NMR characteristics via isotopically labeled monolignols

Contact Info

Product

Resources

About

Syntheses of (1,2-¹³C), (1-¹³C) and (3-¹³C) Coniferyl Alcohol

Preparation of Carbon‐14‐Labeled Compounds via Multi‐Carbon Building Blocks of the [ ¹⁴ C]Carbon Dioxide Tree