General and Secondary Metabolism Role of Chirality at Sulfur

1 General and Secondary Metabolism. Role of Chirality at Sulfur 

The general metabolism of sulfur, extensively described in many texts of biological sciences, is not considered in this article some topics (e.g. metallo-enzymes) are discussed elsewhere in this volume (Chapter 11.2). Our focus is on sulfur-containing secondary metabolites in microorganisms and plants. In view of the vast literature, we can only provide an eclectic account citing recent work where possible. 

Certain chalcogen structures display the phenomenon of chirality (Chapter 10.2). As with carbon,2 chirality at sulfur can influence physiological events there are many stereoselectivities in the interactions of chiral sulfur compounds with enzymes and receptor molecules. Sulfur chirality in secondary metabolites is most commonly observed with sulfonium salts, sulfoxides and sulfoximines.3 

2 Overview of Structural Types for Sulfur-Containing Secondary Metabolites 

In 1977, a survey of low molecular weight sulphur-containing compounds in Nature ,4 noted that these secondary metabolites had little more in common than the possession of one or more sulfur atoms. The reader was left with a kaleidoscopic impression of almost 80 chemical structures. A comprehensive review today would require many hundreds of sulfur-containing chemical structures. 

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