β‐Amino Acid Biosynthesis

Spiteller, Peter

doi:10.1002/9783527631766.ch4

Cited by 13 publications

(10 citation statements)

References 181 publications

(299 reference statements)

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“…53 It is known that, in mammals, degradation of uracil and thymine leads to b-alanine and (R)-b-aminoisobutyric acid, respectively. 4,54,55 Additionally, degradation of L-valine to (S)-b-aminoisobutyric acid in mammals is recognized. 4,55 In yeasts, spermine is known to be a source of b-alanine via 3-aminopropanal.…”

Section: Sugar-b-amino Acid Hybridsmentioning

confidence: 99%

“…4,54,55 Additionally, degradation of L-valine to (S)-b-aminoisobutyric acid in mammals is recognized. 4,55 In yeasts, spermine is known to be a source of b-alanine via 3-aminopropanal. 56 Thus, b-alanine and b-aminoisobutyric acid occur widely in various organisms.…”

Section: Sugar-b-amino Acid Hybridsmentioning

confidence: 99%

“…Biosynthetic pathways for b-amino acids have been extensively studied. Spiteller has elegantly reviewed the occurrence of b-amino acids and their biosynthetic pathways in Amino Acids, Peptides and Proteins in Organic Chemistry in 2009, 4 and also summarized most of the known b-amino acid-containing natural products in Enantioselective Synthesis of b-Amino Acids in 2005, 5 and in the chapter "b-Amino Acids in Nature" in Highlights in Bioorganic Chemistry in 2004. 6 In addition, Walsh and Khosla have summarized the biosynthesis of the major classes of nonproteinogenic amino acids including some b-amino acids in nonribosomal peptides and hybrids of nonribosomal peptide-polyketides in 2013.…”

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confidence: 99%

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Biosynthesis of natural products containing β-amino acids

2014

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Covering: up to January, 2014. We focus here on β-amino acids as components of complex natural products because the presence of β-amino acids produces structural diversity in natural products and provides characteristic architectures beyond those of ordinary α-L-amino acids, thus generating significant and unique biological functions in nature. In this review, we first survey the known bioactive β-amino acid-containing natural products including nonribosomal peptides, macrolactam polyketides, and nucleoside-β-amino acid hybrids. Next, the biosynthetic enzymes that form β-amino acids from α-amino acids and the de novo synthesis of β-amino acids are summarized. Then, the mechanisms of β-amino acid incorporation into natural products are reviewed. Because it is anticipated that the rational swapping of the β-amino acid moieties with various side chains and stereochemistries by biosynthetic engineering should lead to the creation of novel architectures and bioactive compounds, the accumulation of knowledge regarding β-amino acid-containing natural product biosynthetic machinery could have a significant impact in this field. In addition, genome mining of characteristic β-amino acid biosynthetic genes and unique β-amino acid incorporation machinery could lead to the discovery of new β-amino acid-containing natural products.

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Section: Sugar-b-amino Acid Hybridsmentioning

confidence: 99%

Section: Sugar-b-amino Acid Hybridsmentioning

confidence: 99%

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confidence: 99%

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Biosynthesis of natural products containing β-amino acids

2014

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“…In nature, β‐amino acids are rare substances by comparison with proteinogenic α‐( l )‐amino acids (Spiteller, ; Walsh et al ., ). Most β‐amino acids serve as building blocks for small bioactive peptide scaffolds produced as metabolites by various microorganisms (Takaishi et al ., ; Kudo et al ., ).…”

Section: Introductionmentioning

confidence: 99%

The priming molecule β‐aminobutyric acid is naturally present in plants and is induced by stress

et al. 2016

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The defense system of a plant can be primed for increased defense, resulting in an augmented stress resistance and/or tolerance. Priming can be triggered by biotic and abiotic stimuli, as well as by chemicals such as β-aminobutyric acid (BABA), a nonprotein amino acid considered so far a xenobiotic. Since the perception mechanism of BABA has been recently identified in Arabidopsis thaliana, in the present study we explored the possibility that plants do synthesize BABA. After developing a reliable method to detect and quantify BABA in plant tissues, and unequivocally separate it from its two isomers α- and γ-aminobutyric acid, we measured BABA levels in stressed and nonstressed A. thaliana plants, and in different plant species. We show that BABA is a natural product of plants and that the endogenous levels of BABA increase rapidly after infection with necrotrophic, biotrophic and hemibiotrophic pathogens, as well as after salt stress and submergence. Our results place the rise in endogenous BABA levels to a point of convergence in plant stress response and provide biological significance to the presence of a receptor in plants. These findings can explain the extremely widespread efficacy of BABA and open the way to unravel the early steps of priming.

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“…Among various functional compounds, fluorinated amino acids (FAAs) and their derivatives have proven to be of particular interest in numerous fields of science and technology, as such compounds have exhibited widespread applications. For instance, FAAs are frequently used as biological tracers, mechanistic probes, enzyme inhibitors, β-lactam antibiotics, biomedical agents for blood pressure and allergy control, and key compositions for tuning protein structure . Because of their interesting functions, the development of reliable synthetic approaches enabling the efficient synthesis of fluorinated amino acid derivatives is highly desirable.…”

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Construction of Fluorinated Amino Acid Derivatives via Cobalt-Catalyzed Oxidative Difunctionalization of Cyclic Ethers

et al. 2022

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Via difunctionalization of the α- and β-sites of cyclic ethers, we herein demonstrate a new synthetic method for the efficient construction of novel fluorinated γ-amino acid esters by employing a CoBr2/m-CPBA catalyst system. Several cyclic ethers were transformed in combination with a vast range of amines and ethyl trifluoropyruvate into the desired products under mild conditions, making this method a practical platform to enrich the library of fluorinated amino acid derivatives from cost-effective and readily available feedstocks.

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β‐Amino Acid Biosynthesis

Cited by 13 publications

References 181 publications

Biosynthesis of natural products containing β-amino acids

Biosynthesis of natural products containing β-amino acids

The priming molecule β‐aminobutyric acid is naturally present in plants and is induced by stress

Construction of Fluorinated Amino Acid Derivatives via Cobalt-Catalyzed Oxidative Difunctionalization of Cyclic Ethers

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