Chemistry and biology of the aminosulfonate cysteinolic acid: discovery, distribution, synthesis and metabolism

Burchill, Laura; Williams, Spencer J.

doi:10.1039/d2ob00362g

Org. Biomol. Chem.

2022

DOI: 10.1039/d2ob00362g

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Chemistry and biology of the aminosulfonate cysteinolic acid: discovery, distribution, synthesis and metabolism

Laura Burchill

Spencer J. Williams

Abstract: This review provides an historical account of the poorly understood aminosulfonic acid d-cysteinolic acid. Its discovery, occurrence within marine organisms, routes for chemical synthesis, and speculation surrounding its metabolism are discussed.

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2024

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Cited by 2 publications

References 78 publications

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Differentiation of aminohydroxypropanesulfonic acid structural isomers using tandem mass spectrometry-based methods

Anh Nguyen,

Bowen,

Burchill

et al. 2024

International Journal of Mass Spectrometry

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Differentiation of aminohydroxypropanesulfonic acid structural isomers using tandem mass spectrometry-based methods

Anh Nguyen,

Bowen,

Burchill

et al. 2024

International Journal of Mass Spectrometry

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Aminolipids in bacterial membranes and the natural environment

Liu,

Silvano,

et al. 2024

The ISME Journal

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Our comprehension of membrane function has predominantly advanced through research on glycerophospholipids, also known as phosphoglycerides, which are glycerol phosphate-based lipids found across all three domains of life. However, in bacteria, a perplexing group of lipids distinct from glycerol phosphate-based ones also exists. These are amino acid-containing lipids that form an amide bond between an amino acid and a fatty acid. Subsequently, a second fatty acid becomes linked, often via the 3-hydroxy group on the first fatty acid. These amide-linked aminolipids have, as of now, been exclusively identified in bacteria. Several hydrophilic head groups have been discovered in these aminolipids including ornithine, glutamine, glycine, lysine, and more recently, a sulfur-containing non-proteinogenic amino acid cysteinolic acid. Here, we aim to review current advances in the genetics, biochemistry and function of these aminolipids as well as giving an ecological perspective. We provide evidence for their potential significance in the ecophysiology of all major microbiomes i.e. gut, soil and aquatic as well as highlighting their important roles in influencing biological interactions.

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Chemistry and biology of the aminosulfonate cysteinolic acid: discovery, distribution, synthesis and metabolism

Abstract: This review provides an historical account of the poorly understood aminosulfonic acid d-cysteinolic acid. Its discovery, occurrence within marine organisms, routes for chemical synthesis, and speculation surrounding its metabolism are discussed.

Cited by 2 publications

References 78 publications

Differentiation of aminohydroxypropanesulfonic acid structural isomers using tandem mass spectrometry-based methods

Differentiation of aminohydroxypropanesulfonic acid structural isomers using tandem mass spectrometry-based methods

Aminolipids in bacterial membranes and the natural environment

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