Biosynthesis of Chlorinated Lactylates in Sphaerospermopsis sp. LEGE 00249

Lactylates are an important group of molecules in the food and cosmetic industries. A series of natural halogenated 1-lactylates, chlorosphaerolactylates (1–4), were recently reported from Sphaerospermopsis sp. LEGE 00249. Here, we identify the cly biosynthetic gene cluster, containing all the neces...

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Bibliographic Details
Published inJournal of natural products (Washington, D.C.) Vol. 84; no. 2; pp. 278 - 286
Main Authors Abt, Kathleen, Castelo-Branco, Raquel, Leão, Pedro N
Format Journal Article
LanguageEnglish
Published United States American Chemical Society and American Society of Pharmacognosy 26.02.2021
Subjects
Biosynthetic Pathways
Computational Biology
Cyanobacteria - metabolism
Esters - chemistry
Halogenation
Lactic Acid - chemistry
Lauric Acids - chemistry
Molecular Structure
Multigene Family
Pyruvic Acid
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Summary:Lactylates are an important group of molecules in the food and cosmetic industries. A series of natural halogenated 1-lactylates, chlorosphaerolactylates (1–4), were recently reported from Sphaerospermopsis sp. LEGE 00249. Here, we identify the cly biosynthetic gene cluster, containing all the necessary functionalities for the biosynthesis of the natural lactylates, based on in silico analyses. Using a combination of stable isotope incorporation experiments and bioinformatic analysis, we propose that dodecanoic acid and pyruvate are the key building blocks in the biosynthesis of 1–4. We additionally report minor analogues of these molecules with varying alkyl chains. This work paves the way to accessing industrially relevant lactylates through pathway engineering.
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ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.0c00950