A New Cyclic alpha-Aminocarboxylic Acid in Berries of Cowberry.

Vahatalo, M. L.; Virtanen, A. I.

doi:10.3891/acta.chem.scand.11-0741

Cited by 61 publications

(10 citation statements)

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“…Ethylene, among other things, is involved in senescence, fruit ripening, and interspecies communication in plants. ACC was isolated from many fruits and plant tissues. − Adams and Yang 15 detected that ethylene is formed from methionine, with ACC as the kinetically and chemically stable intermediate. In the first step, however, methionine is enzymatically converted to SAM ( 48 ).…”

Section: B Internal Nucleophilic Substitution (Sni)cyclopropane Amin...mentioning

confidence: 99%

“…More importantly, cyclopropanes can serve as rigid structural elements, causing reduced conformational flexibility in their annulated, spiro, or di- to oligosubstituted form. Examples in which this can lead to interesting properties are cyclopropane amino acids and peptides with these. − In addition to rigidification, the angles are locked and deviate from the standard tetrahedral angle. Thus, angles are reduced within the ring, and substituent angles are enlarged in spiro or 1,1-disubstituted cyclopropanes (to about 118° versus 109.5° in saturated systems, Scheme ).…”

Section: Introductionmentioning

confidence: 99%

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Biosynthesis and Metabolism of Cyclopropane Rings in Natural Compounds

2003

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Section: B Internal Nucleophilic Substitution (Sni)cyclopropane Amin...mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Biosynthesis and Metabolism of Cyclopropane Rings in Natural Compounds

2003

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“…This is achieved by transcriptional and posttranslational regulation of the ethylene biosynthesis enzymes and the adjacent Yang cycle, and by transport and conjugation of the ethylene precursor 1‐aminocyclopropane‐1‐carboxylic acid (ACC). Although ACC was first identified in plants in the 1950s (Burroughs, 1957; Vahatalo & Virtanen, 1957), only recently new evidence has been gathered which showed that ACC also acts as a signalling molecule in plants, independently of ethylene. ACC has been shown to regulate cell wall metabolism (Xu et al ., 2008; Tsang et al ., 2011), guard cell differentiation (Yin et al ., 2019), vegetative development (Tsuchisaka et al ., 2009; Vanderstraeten et al ., 2019) and pollen tube attraction (Mou et al ., 2020) in Arabidopsis ( Arabidopsis thaliana ).…”

Section: Introduction To the Ethylene Biosynthesis Pathwaymentioning

confidence: 99%

The regulation of ethylene biosynthesis: a complex multilevel control circuitry

2020

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The gaseous plant hormone ethylene is produced by a fairly simple two-step biosynthesis route. Despite this pathway's simplicity, recent molecular and genetic studies have revealed that the regulation of ethylene biosynthesis is far more complex and occurs at different layers. Ethylene production is intimately linked with the homeostasis of its general precursor S-adenosyl-Lmethionine (SAM), which experiences transcriptional and posttranslational control of its synthesising enzymes (SAM synthetase), as well as the metabolic flux through the adjacent Yang cycle. Ethylene biosynthesis continues from SAM by two dedicated enzymes: 1-aminocyclopropane-1-carboxylic (ACC) synthase (ACS) and ACC oxidase (ACO). Although the transcriptional dynamics of ACS and ACO have been well documented, the first transcription factors that control ACS and ACO expression have only recently been discovered. Both ACS and ACO display a type-specific posttranslational regulation that controls protein stability and activity. The nonproteinogenic amino acid ACC also shows a tight level of control through conjugation and translocation. Different players in ACC conjugation and transport have been identified over the years, however their molecular regulation and biological significance is unclear, yet relevant, as ACC can also signal independently of ethylene. In this review, we bring together historical reports and the latest findings on the complex regulation of the ethylene biosynthesis pathway in plants.

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“…DISCUSSION The initial bioinformatic analysis of NocJ suggested that, akin to the ACC deaminases, it could also utilize the cofactor PLP for its catalytic function. The amino acid ACC was first identified from fruit juices in the late 1950s, and was later established as the key intermediate in the biosynthesis of the plant hormone ethylene (42)(43)(44). The enzyme ACC deaminase was first identified in Pseudomonas sp.…”

Section: Analysis Of Nocj-mentioning

confidence: 99%

Mutational Analysis and Characterization of Nocardicin C-9′ Epimerase

Kelly

Townsend

2004

Journal of Biological Chemistry

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The biosynthetic gene cluster for the nocardicin A producer Nocardia uniformis subsp. tsuyamanensis ATCC 21806 was recently identified. Nocardicin A is the most potent of a series of monocyclic ␤-lactam antibiotics produced by this organism. Its activity has been attributed to a syn-configured oxime moiety and a D-homoseryl side chain attached through an unusual ether linkage to the core nocardicin framework. Notably present in the nocardicin biosynthetic gene cluster is nocJ, encoding a protein with sequence similarity to the pyridoxal 5 -phosphate (PLP)-dependent 1-aminocyclopropane-1-carboxylic acid deaminases. Insertional mutagenesis of nocJ abolished nocardicin A production, while the L-homoseryl isomer, isonocardicin A, was still observed. Expression of the disrupted nocJ gene in trans was sufficient to restore production of nocardicin A in the disruption mutant. Heterologous expression, purification, and in vitro characterization of NocJ by UV spectroscopy, cofactor reduction, chiral HPLC analysis of the products and their exchange behavior in deuterium oxide led to confirmation of its role as the PLP-dependent nocardicin C-9 epimerase responsible for interconversion of the nocardicin homoseryl side chain in both nocardicin A with isonocardicin A, and nocardicin C with isonocardicin C. NocJ is the first member of a new class of ␤-lactam aminoacyl side chain epimerases, the first two classes being the evolutionarily distinct prokaryotic PLP-dependent isopenicillin N epimerase and the fungal isopenicillin N epimerase two protein system.

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A New Cyclic alpha-Aminocarboxylic Acid in Berries of Cowberry.

Cited by 61 publications

References 0 publications

Biosynthesis and Metabolism of Cyclopropane Rings in Natural Compounds

Biosynthesis and Metabolism of Cyclopropane Rings in Natural Compounds

The regulation of ethylene biosynthesis: a complex multilevel control circuitry

Mutational Analysis and Characterization of Nocardicin C-9′ Epimerase

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