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Sulfur Assimilation

Sulfur Assimilation

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...

Preparation and Reactions of Sulfides

Preparation and Reactions of Sulfides

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.

Structure and Nomenclature of Thiols and Sulfides

Structure and Nomenclature of Thiols and Sulfides

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,...

Preparation and Reactions of Thiols

Preparation and Reactions of Thiols

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.

Electrophilic Aromatic Substitution: Sulfonation of Benzene

Electrophilic Aromatic Substitution: Sulfonation of Benzene

Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.

Amines to Sulfonamides: The Hinsberg Test

Amines to Sulfonamides: The Hinsberg Test

The Hinsberg test is a method to identify primary, secondary and tertiary amines, named after its pioneer, Oscar Hinsberg. Here, amines are treated with benzenesulfonyl chloride, also known as the Hinsberg reagent, in the presence of an excess of aqueous base, followed by acidification. Based on the nature of the amines, different changes are observed.
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing sulfonyl...

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Targeting Cysteine Thiols for in Vitro Site-specific Glycosylation of Recombinant Proteins

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Isolable small-molecule cysteine sulfenic acid.

Tsukasa Sano¹, Ryosuke Masuda¹, Shohei Sase¹

¹Department of Chemistry, School of Science, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, 152-8551, Japan. goto@chem.titech.ac.jp.

Chemical Communications (Cambridge, England)

|February 18, 2021

Summary

Researchers synthesized a stable small-molecule cysteine sulfenic acid (Cys-SOH) using a molecular cradle. This biorepresentative model demonstrates useful biological reactivity for further studies.

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Area of Science:

Chemical synthesis
Biochemistry
Structural biology

Background:

Cysteine sulfenic acids (Cys-SOH) are transient and challenging to study.
Understanding Cys-SOH is crucial for various biological processes.
A stable model is needed to investigate Cys-SOH reactivity.

Purpose of the Study:

To synthesize and characterize an isolable small-molecule cysteine sulfenic acid.
To establish the structure of the synthesized Cys-SOH.
To evaluate the biological relevance and reactivity of the Cys-SOH model.

Main Methods:

Direct oxidation of a cysteine thiol precursor.
Protection of the sulfenic acid using a molecular cradle.
X-ray crystallographic analysis for structural determination.
Biologically relevant reactivity assays.

Main Results:

Successfully synthesized an isolable small-molecule cysteine sulfenic acid.
Established the precise molecular structure via X-ray crystallography.
Demonstrated biorepresentative reactivity, confirming its utility as a model.

Conclusions:

A stable, small-molecule Cys-SOH model has been developed.
The molecular cradle effectively protects the reactive sulfenic acid moiety.
This model provides a valuable tool for studying cysteine sulfenic acid chemistry in biological systems.