Cyclopropane Fatty Acid Biosynthesis in Bacterial Membranes

Bacterial cyclopropane fatty acids (CFAs) are specialised membrane lipids in which a three-membered cyclopropane ring is introduced into the hydrocarbon chain of unsaturated phospholipids. This modification is catalysed by cyclopropane fatty acid synthase (CFAS), an S-adenosylmethionine (SAM)-dependent methyltransferase that transfers a methylene group across a double bond to yield the cyclopropane ring. The formation of CFAs typically occurs during the transition from exponential to stationary phase and is upregulated in response to environmental stresses such as solvent exposure, low pH and temperature shifts. By rigidifying the lipid bilayer and modulating membrane fluidity, CFAs enhance bacterial resilience under adverse conditions. Beyond their physiological role in stress adaptation, CFAS enzymes have attracted interest as biocatalysts for sustainable cyclopropanation reactions, offering stereoselective construction of cyclopropyl motifs under mild, aqueous conditions. Recent advances have deepened mechanistic understanding of substrate recognition, ring-closing chemistry and the structural basis for enantioselectivity, while also revealing opportunities for engineering CFAS variants with tailored activity and expanded substrate scope. The study of CFA biosynthesis therefore spans fundamental microbiology, membrane biophysics and applied biocatalysis, with implications for antimicrobial strategy and industrial chemistry.

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Cyclopropane Fatty Acid Biosynthesis in Bacterial Membranes publication trend

The graph below shows the total number of articles in cyclopropane fatty acid biosynthesis in bacterial membranes across all publications each year (not limited to Nature Index journals).

Technical terms

Cyclopropane fatty acids (CFAs): Fatty acids containing a three-membered cyclopropane ring, formed by modification of unsaturated membrane lipids.

Cyclopropane fatty acid synthase (CFAS): An S-adenosylmethionine-dependent methyltransferase that catalyses methylene transfer across a carbon-carbon double bond to generate a cyclopropane ring in phospholipids.

S-adenosylmethionine (SAM): A universal methyl donor molecule used by methyltransferases to transfer methyl groups in biosynthetic pathways.

Enantioselectivity: The preference of a catalytic reaction to produce one enantiomer over its mirror image, crucial for stereospecific synthesis.

References

1. Insights into E. coli Cyclopropane Fatty Acid Synthase (CFAS) Towards Enantioselective Carbene Free Biocatalytic Cyclopropanation.. Angewandte Chemie International Edition (2024).
2. Cyclopropane fatty acids are involved in organic solvent tolerance but not in acid stress resistance in Pseudomonas putida DOT‐T1E. Microbial Biotechnology (2009).
3. Enzymatic Synthesis of Cyclopropane Fatty Acids Catalyzed by Bacterial Extracts. Journal of Biological Chemistry (1963).