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Sulfur Assimilation01:20

Sulfur Assimilation

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Sulfur is an essential element in biological systems, contributing to synthesizing key biomolecules, including amino acids such as cysteine and methionine, and cofactors such as coenzyme A and biotin. Microorganisms primarily assimilate sulfur as sulfate (SO₄²⁻) from the environment, which must undergo a series of biochemical transformations before it can be incorporated into cellular components. As sulfate is highly oxidized, it must undergo assimilatory sulfate reduction to...
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Preparation and Reactions of Sulfides02:26

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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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Preparation and Reactions of Thiols02:33

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Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
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Sulfur, an important element in the chemical makeup of proteins, is recycled through the atmosphere and aquatic and terrestrial environments. Found in the atmosphere as sulfur dioxide (SO2), sulfur is released by decaying organisms, weathered rocks, geothermal vents, volcanos, and burning fossil fuels. It is deposited into the ecosystem, cycled through the biotic community, and either released back into the atmosphere as gas or deposited in marine sediment for long-term storage and eventual...
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Thiols and sulfides are sulfur analogs of alcohols and ethers, respectively, where the sulfur atom takes the place of the oxygen atom. Thus, thiols are generally represented as RSH, where R is an alkyl substituent and —SH is the functional group. On the other hand, in sulfides, the central sulfur atom is bonded to two hydrocarbon groups on either side. Depending upon the type of group, sulfides can be either symmetrical or asymmetrical. Both thiols and sulfides display a bent geometry,...
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Microbiological versus Chemical Reductive Sulfidation: An Experimental and Theoretical Study.

Oriane Della-Negra1, Brieuc Le Cacher de Bonneville1,2, Sébastien Chaussonnerie1

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Microbiological reductive sulfidation (RS) efficiently forms thiols using Desulfovibrio sp.86. This study compares bacterial RS with chemical methods, revealing distinct mechanisms and potential for organic synthesis.

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Area of Science:

  • Biochemistry
  • Organic Chemistry
  • Microbiology

Background:

  • Microbiological reductive sulfidation (RS) is an understudied but efficient method for thiol synthesis.
  • The sulfate-respiring bacterium Desulfovibrio sp.86 exhibits RS activity.
  • Previous work demonstrated its ability to transform the pesticide chlordecone.

Purpose of the Study:

  • To evaluate the substrate range of Desulfovibrio sp.86 for RS using 28 carbonyl compounds.
  • To compare the mechanisms of microbiological RS with chemical RS.
  • To rationalize observed trends using experimental and theoretical analyses.

Main Methods:

  • Tested 28 carbonyl compounds for bacterial RS using Desulfovibrio sp.86.
  • Investigated chemical RS using phosphorus pentasulfide (P4S10) and a designed protocol for direct thiol conversion.
  • Employed density functional theory (DFT) calculations to analyze structural, electronic, and thermodynamic parameters.

Main Results:

  • Chemical RS of some carbonyls with P4S10 directly yielded thiols, suggesting a single-electron transfer mechanism.
  • Desulfovibrio sp.86 transformed various aldehydes and ketones into thiols without forming thiones.
  • Bacterial RS of aldehydes correlated with bacterial growth, unlike chemical RS.

Conclusions:

  • Microbiological and chemical RS likely proceed via distinct pathways.
  • The selectivity differences offer potential for novel applications in organic synthesis.
  • Desulfovibrio sp.86 demonstrates versatility in biotransforming carbonyls to thiols.