Biosynthesis in vitro of 2-(3-amino-3-carboxypropyl)-isoxazolin-5-one, the neurotoxic amino acid in Lathyrus odoratus.

Ikegami, Fumio; Sakai, Ritsuko; Ishikawa, Tsutomu; Kuo, Yao‐Haur; Lambein, Fernand; Murakoshi, Isamu

doi:10.1248/bpb.16.732

Cited by 10 publications

(4 citation statements)

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“…Examples of N-ACP transfer are mainly from RNA modifications, such as 3-(3- amino-3-carboxypropyl) uridine [13–16] or acp 3 U and 1-methyl-3-(3-amino-3-carboxypropyl) pseudouridine or m 1 acp 3 Ψ̃ [17, 18]. An ACP-transfer reaction was also demonstrated in the biosynthesis of 2-(3-amino-3-carboxypropyl)-isoxazolin-5-one, a neurotoxic amino acid from Lathyrus odoratus [19]. A reaction that is closely related to the ACP-transfer reaction is found in polyamine biosynthesis, in which SAM is decarboxylated to decarboxy-SAM and then the 3-aminopropyl group is transferred[20].…”

Section: Sam-dependent N- or O-alkylation: Nucleophilic Mechanismmentioning

confidence: 99%

S-Adenosylmethionine-dependent alkylation reactions: When are radical reactions used?

Lin

2011

Bioorganic Chemistry

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S-adenosylmethionine (SAM) is a versatile small molecule used in many biological reactions. This review focuses on the mechanistic consideration of SAM-dependent methylation and 3-amino-3-carboxypropylation reactions. Special emphasis is given to methylation and 3-amino-3-carboxypropylation of carbon atoms, for which both nucleophilic mechanisms and radical mechanisms are used, depending on the specific enzymatic reactions. What is the logic behind Nature’s choice of different reaction mechanisms? Here I aim to rationalize the choice of different reaction mechanisms in SAM-dependent alkylation reaction by analyzing a few enzymatic reactions in depth. These reactions include SAM-dependent cyclopropane fatty acid synthesis, DNA cytosine methylation, RNA adenosine C2 and C8 methylation, and 3-amino-3-carboxypropylation involved in diphthamide biosynthesis and wybutosine biosynthesis.

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Section: Sam-dependent N- or O-alkylation: Nucleophilic Mechanismmentioning

confidence: 99%

S-Adenosylmethionine-dependent alkylation reactions: When are radical reactions used?

Lin

2011

Bioorganic Chemistry

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“…108 In vitro assays using enzyme extracts from L. odoratus indicated that the biosynthesis of ACI 12, the homologue of BIA 11, proceeds via isoxazolin-5-one as well as S-adenosyl-L-methionine as substrates. 109,110 As described in previous chapters, the isoxazolin-5-one and 3-NPA moieties occur in Astragalus species in the same molecule, as found in compound 4. Whether there is a relationship between the metabolic pathways of both moieties, similar to the biosynthesis of these motifs in leaf beetles, is not yet known.…”

Section: Plantsmentioning

confidence: 75%

A tale of four kingdoms – isoxazolin-5-one- and 3-nitropropanoic acid-derived natural products

et al. 2017

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Covering up to September 2016This review reports on natural compounds that derive from the isoxazolinone ring as well as the 3-nitropropanoic acid (3-NPA) moiety. These structural elements occur in compounds that have been identified in plants, insects, bacteria and fungi. In particular, plants belonging to the family of legumes produce such compounds. In the case of insects, isoxazolin-5-one and 3-NPA derivatives were found in leaf beetles of the subtribe Chrysomelina. A number of these natural products have been synthesized so far. In the case of the single compound 3-NPA, several synthetic strategies have been reported and some of the most efficient routes are reviewed. The toxicity of 3-NPA results from its ability to bind covalently to the catalytic center of succinate dehydrogenase causing irreversible inhibition of mitochondrial respiration. As a motif that is produced by many species of plants, leaf beetles and fungi, different detoxification mechanisms for 3-NPA have evolved in different species. These mechanisms are based on amide formation of 3-NPA with amino acids, reduction to β-alanine, ester formation or oxidation to malonic acid semialdehyde. The biosynthetic pathways of 3-NPA and isoxazolin-5-one moieties have been studied in fungi, plants and leaf beetles. In the case of fungi, 3-NPA derives from aspartate, while leaf beetles use essential amino acids such as valine as ultimate precursors. In the case of plants, it is supposed that malonate serves as a precursor of 3-NPA, as indicated by feeding of C-labeled precursors to Indigofera spicata. In other leguminous plants it is suggested that asparagine is incorporated into compounds that derive from isoxazolin-5-one, which was indicated byC-labeled compounds as well. In the case of leaf beetles it was demonstrated that detection of radioactivity after C-labeling from a few precursors is not sufficient to unravel biosynthetic pathways.

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“…57 Additional ACP transferases with small molecule substrates are also involved in the biosynthesis of isonocardicin C (18), 58,59 betaine lipid (19), 60 discadenine (20) 61,62 and 2-(3-amino-3carboxypropyl)-isoxazolin-5-one (ACI) (21) (Fig. 6); 63,64 however, none of these enzymes appear to be homologous to the aforementioned ACP transferases NAS, MtNAS, CntL and MccD. With the exception of ACI, ACP transfer from SAM is respectively catalyzed in these cases by NAT, BtaA and discadenine synthase.…”

Section: Natural Product Reports Reviewmentioning

confidence: 99%

“…With the exception of ACI, ACP transfer from SAM is respectively catalyzed in these cases by NAT, BtaA and discadenine synthase. However, while the in vitro formation of ACI is known to require a partially puried enzyme fraction from sweet pea seedlings as well as the presence of ATP and magnesium, 63,64 the responsible enzyme as well as the role of ATP remains elusive.…”

Section: Natural Product Reports Reviewmentioning

confidence: 99%

S-Adenosylmethionine: more than just a methyl donor

et al. 2023

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Biosynthesis in vitro of 2-(3-amino-3-carboxypropyl)-isoxazolin-5-one, the neurotoxic amino acid in Lathyrus odoratus.

Cited by 10 publications

References 0 publications

S-Adenosylmethionine-dependent alkylation reactions: When are radical reactions used?

S-Adenosylmethionine-dependent alkylation reactions: When are radical reactions used?

A tale of four kingdoms – isoxazolin-5-one- and 3-nitropropanoic acid-derived natural products

S-Adenosylmethionine: more than just a methyl donor

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