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Degradation of Sulfide Linkages Between Isoprenes by Lipid Peroxidation Catalyzed by Manganese Peroxidase

Degradation of Sulfide Linkages Between Isoprenes by Lipid Peroxidation Catalyzed by Manganese Peroxidase

Shin Sato, Yasunori Ohashi, Masaaki Kojima, Takahito Watanabe, Yoichi Honda, Takashi Watanabe

Chemosphere. 2009 Oct;77(6):798-804.

PMID: 19740510

Abstract:

Scission of sulfide linkages in vulcanized rubber has been a major concern since the early 20th century, because devulcanization is a key process for recycling waste rubber products as polymer materials that pose low environmental risks. We herein demonstrate that lipid peroxidation (LPO) of linoleic acid by manganese peroxidase (MnP), a proposed lignin-degradation system in the early stage of selective white rot fungi, cleaves sulfide bond in a model rubber compound, di(2-methylpent-2-enyl) sulfide, to 2,4-dimethylthiophene and 2-methyl-2-pentenal. The major intermediate of the LPO process, 2,4-decadienal was directly oxidized by MnP to cleave the sulfur-carbon bond. We propose that electrophilic radicals from 2,4-decadienal abstract one electron from a sulfur atom of the model compound to produce the sulfur radical cation intermediate, which in turn reacts with molecular oxygen to cleave the sulfur-carbon bond. The discovery of free radical-mediated scission of sulfide bond coupled with Mn oxidation provides a novel strategy for recycling vulcanized rubber wastes.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP623369	2-Methyl-2-pentenal		623-36-9	Price

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