Interconnected Set of Enzymes Provide Lysine Biosynthetic Intermediates and Ornithine Derivatives as Key Precursors for the Biosynthesis of Bioactive Secondary Metabolites
Abstract
:1. Introduction
2. Biosynthesis of α-Aminoadipic Acid in Filamentous Fungi and Bacteria
2.1. Biosynthesis of a-AAA and Interconversion of a-AAA and Lysine. Several Different Pathways Converge on the Biosynthesis of α-AAA in Filamentous Fungi (Figure 3)
2.1.1. α-AAA Is Formed in Fungi as an Intermediate of the Lysine Pathway
2.1.2. Five Genes Encode Enzymes Similar to the Saccharopine Reductase and Saccharopine Dehydrogenase in Filamentous Fungi: A Possible Role for These Multiple Enzymes
2.2. Formation of α-AAA by Catabolism of Lysine
2.2.1. LAT-Dependent Biosynthesis of α-AAA in Filamentous Fungi and Bacteria
2.2.2. Lysine 6-Dehydrogenase-Dependent Biosynthesis of α-AAA in Bacteria
3. Pipecolic Acid Biosynthesis in Fungi, Plants, and Bacteria
3.1. Biosynthetic Routes and Enzymes Involved in the Formation of Pipecolic Acid in Fungi: Interconversion of Lysine and Pipecolic Acid
3.2. Biosynthesis of Pipecolic Acid in Plants
3.3. One Step Biosynthesis of Pipecolic Acid in Bacteria: Lysine Cyclodeaminases
4. 4-Oxopipecolic Acid and 3-Hydroxypicolinic Acid Precursors Related to Pipecolic Acid
4.1. Biosynthesis of 4-Oxo-L-Pipecolic Acid
4.2. Biosynthesis of 3-Hydroxypicolinic Acid
5. Cadaverine and Putrescine Precursors of Desferrioxamine-Type Siderophores
5.1. Biosynthesis of Desferrioxamines from Cadaverine
5.2. L-δ-N-Hydroxyornithine and D-δ-N-Formyl-N-Hydroxyornithine in the Biosynthesis of Bacterial Peptide Siderophores: Coelichelins
6. Siderophores Derived from Ornithine in Filamentous Fungi
6.1. Fungal Siderophores Synthesized by Condensation of Acylated N5-Hydroxylornithine Units: Fusarinins
6.2. Siderophores Synthesized by NRPSs in Filamentous Fungi: Ferrichromes
6.3. Coprogens
7. Role of Intracellular and Extracellular Siderophores
8. Summary and Future Outlook
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
Abbreviations
References
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SM Precursor | Precursor Synthesizing Enzyme(s) | Secondary Metabolite (SM) | Producer Strain | Reference | |
---|---|---|---|---|---|
1 | α-Aminoadipic acid (α-AAA) | α-Ketoadipate aminotransferase | Penicillins Cephalosporin C Cephamycins | Penicillium chrysogenum Acremonium chrysogenum Streptomyces clavuligerus | [5,18] |
2 | α-Aminoadipic semialdehyde (P6C) | α-AAA reductase Lysine-6-aminotransferase | Penicillins, Cephalosporin C Cephamycins | P. chrysogenum A. chrysogenum S. clavuligerus | [19,20,21] |
3 | Saccharopine | Saccharopine reductase and Pipecolate oxidoreductase | Pipecolic acid | Most fungi | [22,23,24] |
4 | 4-oxo-pipecolic acid | Pipecolate monoxygenase P450 | Swainsonine, Slaframine | Slafractonia leguminicola Metarhizium anisopliae Undifilum oxytropis | [5] |
5 | Pipecolic acid | Lysine cyclodeaminase | Rapamycin Pristinamycin I Tacrolimus | Streptomyces hygroscopicus Streptomyces pristinaespiralis Streptomyces tsukubaensis | [25,26,27] |
6 | 3-Hydroxypicolinic acid | Lysine-2-aminotransferase with dehydrase activity | Pristinamycin I Virginiamycin | S. pristinaespiralis Streptomyces virginiae | [28,29] |
7 | Cadaverine | Lysine decarboxylase | Desferrioxamines | Streptomyces coelicolor Streptomyces pilosus | [30] |
8 | N5-Hydroxyornithine N5-Formyl-N5-Hydroxy- ornithine | N5-ornithine monooxygenase N5-hydroxyornithine acyltransferase | Coelichelin | S. coelicolor Streptomyces ambofaciens | [31,32,33] |
9 | N5-anhydromevalonyl-N5-hydroxyornithine | N5-ornithine monooxygenase Mevalonil CoA ligase Mevalonyl-CoA dehydrase | Fusarinine, TAFC | Many fungi | [34,35] |
10 | N5-acetyl-N5-hydroxyornithine | N5-ornithine monooxygenase N5-hydroxyornithine acyltransferase | Ferrichrocin | Many fungi | [35,36,37,38] |
11 | N5-acetyl-N5-hydroxyornithine | N5-ornithine monooxygenase N5-hydroxyornithine acyltransferase | Coprogen Methyl-coprogen | Many fungi Alternaria alternata | [39] |
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Liras, P.; Martín, J.F. Interconnected Set of Enzymes Provide Lysine Biosynthetic Intermediates and Ornithine Derivatives as Key Precursors for the Biosynthesis of Bioactive Secondary Metabolites. Antibiotics 2023, 12, 159. https://doi.org/10.3390/antibiotics12010159
Liras P, Martín JF. Interconnected Set of Enzymes Provide Lysine Biosynthetic Intermediates and Ornithine Derivatives as Key Precursors for the Biosynthesis of Bioactive Secondary Metabolites. Antibiotics. 2023; 12(1):159. https://doi.org/10.3390/antibiotics12010159
Chicago/Turabian StyleLiras, Paloma, and Juan Francisco Martín. 2023. "Interconnected Set of Enzymes Provide Lysine Biosynthetic Intermediates and Ornithine Derivatives as Key Precursors for the Biosynthesis of Bioactive Secondary Metabolites" Antibiotics 12, no. 1: 159. https://doi.org/10.3390/antibiotics12010159