Biological Interactions Of Sulfur Compounds

The Microbial Sulfur Cycle

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While sulfur-containing antibiotics save many lives, sulfur mustard is a deadly chemical warfare agent. Fossil fuels, coal , petroleum , and natural gas , which are derived from ancient organisms, necessarily contain organosulfur compounds, the removal of which is a major focus of oil refineries. Sulfur shares the chalcogen group with oxygen , selenium , and tellurium , and it is expected that organosulfur compounds have similarities with carbon—oxygen, carbon—selenium, and carbon—tellurium compounds.

A classical chemical test for the detection of sulfur compounds is the Carius halogen method. Organosulfur compounds can be classified according to the sulfur-containing functional groups , which are listed approximately in decreasing order of their occurrence.

Allicin , the active flavor compound in crushed garlic. R - Cysteine , an amino acid containing a thiol group.

Organic Sulfur Compounds

Methionine , an amino acid containing a sulfide. Diphenyl disulfide , a representative disulfide. Dibenzothiophene , a component of crude oil. Perfluorooctanesulfonic acid , a controversial surfactant. Lipoic acid , an essential cofactor of four mitochondrial enzyme complexes.

References

Penicillin core structure, where "R" is the variable group. Sulfanilamide , a sulfonamide antibacterial , called a sulfa drug.

Organosulfur compounds - Wikipedia

Sulfur mustard , a type of sulfide used as a chemical warfare agent. Sulfides are typically prepared by alkylation of thiols. They can also be prepared via the Pummerer rearrangement. In one named reaction called the Ferrario reaction phenyl ether is converted to phenoxathiin by action of elemental sulfur and aluminium chloride. They represent a subclass of sulfides. The thioacetals are useful in " umpolung " of carbonyl groups.

Thioacetals and thioketals can also be used to protect a carbonyl group in organic syntheses. The above classes of sulfur compounds also exist in saturated and unsaturated heterocyclic structures, often in combination with other heteroatoms , as illustrated by thiiranes , thiirenes , thietanes , thietes , dithietanes , thiolanes , thianes , dithianes , thiepanes , thiepines , thiazoles , isothiazoles , and thiophenes , among others. The latter three compounds represent a special class of sulfur-containing heterocycles that are aromatic. The reason for this difference is the higher electronegativity for oxygen drawing away electrons to itself at the expense of the aromatic ring current.

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Yet as an aromatic substituent the thio group is less electron-releasing than the alkoxy group. Dibenzothiophenes see drawing , tricyclic heterocycles consisting of two benzene rings fused to a central thiophene ring, occurs widely in heavier fractions of petroleum. Thiols are structurally similar to the alcohol group, but these functionalities are very different in their chemical properties.

Thiols are more nucleophilic , more acidic, and more readily oxidized. This acidity can differ by 5 p K a units. The difference in electronegativity between sulfur 2.

Aliphatic thiols form monolayers on gold , which are topical in nanotechnology. Certain aromatic thiols can be accessed through a Herz reaction. Longer sulfur chains are also known, such as in the natural product varacin which contains an unusual pentathiepin ring 5-sulfur chain cyclised onto a benzene ring.

Thioesters are prominent in biochemistry, especially in fatty acid synthesis. All of these compounds are well known with extensive chemistry, e. They are of interest in part due to their pharmacological properties. When two different R groups are attached to sulfur, sulfimides are chiral. Sulfoximides also called sulfoximines are tetracoordinate sulfur—nitrogen compounds, isoelectronic with sulfones, in which one oxygen atom of the sulfone is replaced by a substituted nitrogen atom, e.

When two different R groups are attached to sulfur, sulfoximides are chiral.

Much of the interest in this class of compounds is derived from the discovery that methionine sulfoximide methionine sulfoximine is an inhibitor of glutamine synthetase. Sulfonediimines also called sulfodiimines, sulfodiimides or sulfonediimides are tetracoordinate sulfur—nitrogen compounds, isoelectronic with sulfones, in which both oxygen atoms of the sulfone are replaced by a substituted nitrogen atom, e. They are of interest because of their biological activity and as building blocks for heterocycle synthesis. S -Nitrosothiols , also known as thionitrites, are compounds containing a nitroso group attached to the sulfur atom of a thiol, e.

A wide range of organosulfur compounds are known which contain one or more halogen atom "X" in the chemical formulas that follow bonded to a single sulfur atom, e. Compounds with double bonds between carbon and sulfur are relatively uncommon, but include the important compounds carbon disulfide , carbonyl sulfide , and thiophosgene.

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Thioaldehydes are rarer still, reflecting their lack of steric protection " thioformaldehyde " exists as a cyclic trimer. They are typically prepared by the reaction of amides with Lawesson's reagent. Vegetable foods with characteristic flavors due to isothiocyanates include wasabi , horseradish , mustard , radish , Brussels sprouts , watercress , nasturtiums , and capers.

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These compounds are well known with extensive chemistry, e. They are structurally similar to carboxylic acids but more acidic. Thioamides are analogous to amides. Sulfonic acids like trifluoromethanesulfonic acid is a frequently used reagent in organic chemistry. Learn More about VitalSource Bookshelf. CPD consists of any educational activity which helps to maintain and develop knowledge, problem-solving, and technical skills with the aim to provide better health care through higher standards.

It could be through conference attendance, group discussion or directed reading to name just a few examples. We provide a free online form to document your learning and a certificate for your records. Already read this title? Please accept our apologies for any inconvenience this may cause. This product is not available. Toggle navigation Additional Book Information. Description Table of Contents. Summary This text focuses on the biological interactions of sulphur compounds which arise specifically from the presence of the sulphur atom within the molecule.

The book opens with introductory chapters on the chemistry and biology of sulphur, before tackling the field by introducing compounds which share a common chemical combination. In general, following a description of the uses and impact upon the biological field, specific chemical group characteristics are discussed together with the biological activity and structure-activity relationships where known.

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