Azetidine-2-carboxylic acid (abbreviated Aze or Azc) is a plant non-proteinamino acid homologue of proline with the molecular formula C4H7NO2. Aze is a heterocyclic, 4 membered ring with nitrogen as its heteroatom (an azetidine), and a carboxylic acid group substituted on one of the ring carbon atoms. The main difference between Aze and proline is the ring of Aze has four members and the ring of proline has five.[2] Aze has the ability to act as an analog of proline and can be incorporated into proteins in place of proline.
Optically inactive Aze was obtained in small yield from the neurotransmitter GABA by α-bromination, followed by removal of hydrogen bromide from the intermediate γ-amino-α-bromobutyric acid and ring closure by treatment with a barium hydroxide solution. An optically active Aze was obtained by treatment of α,γ-diaminobutyric acid dihydrochloride with a mixture of nitrous and hydrochloric acids to yield γ-amino-α-chlorobutyric acid, followed by elimination of hydrogen chloride and cyclization by treatment with barium hydroxide.[3]
Occurrenceedit
Azetidine-2-carboxylic acid has been known since 1955 to be present in rhizomes and fresh foliage of certain plants. It is known to occur in two species from the Asparagaceae - Convallaria majalis (lily of the valley), and Polygonatum (solomon's seal).
Aze is also found in numerous plants from the bean family Fabaceae, and has also been detected in small quantities in table beets, garden beets, and sugar beets.[4]
Toxicityedit
It has been shown that when Aze is misincorporated into proteins in place of proline, Aze deters the growth of competing vegetation and poisons predators. Other studies have shown effects of Aze resulting in a wide range of toxic and teratogenic disorders, including in a range of malformations, in various animal species including ducks, hamsters, mice, and rabbits.[2]
Misincorporation of Aze into human proteins can alter collagen, keratin, hemoglobin, and protein folding.[5] However, the lack of detailed toxicologic data and the need for more direct evidence about the damaging effects of the misincorporation of Aze on specific proteins are reasons why the toxicity of Aze to humans cannot be determined at this time.[2] Molecular studies of human prolyl- and alanyl-tRNA synthetases suggest that Aze is incorporated in proteins as proline with toxic consequences in vivo.[6] Even if Aze seems to fit into the active site of both tRNA synthetases (due to its double mimicry effect of alanine and proline), it is rejected by alanyl-tRNA synthetases post-transfer editing system.[6]
^ abcRubenstein E.; T. McLaughlin; R.C. Winant; A. Sanchez; M. Eckart; K.M. Krasinska; A. Chien. (2008). "Azetidine-2-carboxylic Acid in the Food Chain". Phytochemistry. 70 (1): 1–5. doi:10.1016/j.phytochem.2008.11.007. PMID 19101705.
^Fowden, L. (1956). "Azetidine-2-carboxylic Acid: a New Cyclic Imino Acid Occurring in Plants". Biochemical Journal. 64 (2): 323–331. doi:10.1042/bj0640323. PMC1199734. PMID 13363844.
^Seigler, David S. (1998). Plant secondary metabolism. Kluwer Academic. p. 222. ISBN0-412-01981-7.
^Rubenstein E.; H. Zhou; K.M. Krasinska; A. Chien; C.H. Becker. (2006). "Azetidine-2-carboxylic Acid in Garden Beets". Phytochemistry. 67 (9): 898–903. doi:10.1016/j.phytochem.2006.01.028. PMID 16516254.
azetidine, carboxylic, acid, abbreviated, plant, protein, amino, acid, homologue, proline, with, molecular, formula, c4h7no2, heterocyclic, membered, ring, with, nitrogen, heteroatom, azetidine, carboxylic, acid, group, substituted, ring, carbon, atoms, main, . Azetidine 2 carboxylic acid abbreviated Aze or Azc is a plant non protein amino acid homologue of proline with the molecular formula C4H7NO2 Aze is a heterocyclic 4 membered ring with nitrogen as its heteroatom an azetidine and a carboxylic acid group substituted on one of the ring carbon atoms The main difference between Aze and proline is the ring of Aze has four members and the ring of proline has five 2 Aze has the ability to act as an analog of proline and can be incorporated into proteins in place of proline Azetidine 2 carboxylic acid 1 Names IUPAC name Azetidine 2 carboxylic acid Identifiers CAS Number 2133 34 8 N 3D model JSmol Interactive image ChEBI CHEBI 6198 Y ChEMBL ChEMBL1165239 Y ChemSpider 15628 Y ECHA InfoCard 100 016 693 EC Number 218 362 5 IUPHAR BPS 4686 KEGG C08267 N PubChem CID 16486 L UNII 5GZ3E0L9ZU N CompTox Dashboard EPA DTXSID0044020 InChI InChI 1S C4H7NO2 c6 4 7 3 1 2 5 3 h3 5H 1 2H2 H 6 7 t3 m0 s1 YKey IADUEWIQBXOCDZ VKHMYHEASA N YInChI 1 C4H7NO2 c6 4 7 3 1 2 5 3 h3 5H 1 2H2 H 6 7 t3 m0 s1Key IADUEWIQBXOCDZ VKHMYHEABQ SMILES O C O C H 1NCC1 Properties Chemical formula C4H7NO2 Molar mass 101 104 g mol Appearance crystalline solid Density 1 275 g cm3 Melting point 215 C 419 F 488 K Boiling point 242 C 468 F 515 K Solubility in water 5 0 g 100 ml Hazards Flash point 100 1 C 212 2 F 373 2 K Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Synthesis 2 Occurrence 3 Toxicity 4 ReferencesSynthesis editOptically inactive Aze was obtained in small yield from the neurotransmitter GABA by a bromination followed by removal of hydrogen bromide from the intermediate g amino a bromobutyric acid and ring closure by treatment with a barium hydroxide solution An optically active Aze was obtained by treatment of a g diaminobutyric acid dihydrochloride with a mixture of nitrous and hydrochloric acids to yield g amino a chlorobutyric acid followed by elimination of hydrogen chloride and cyclization by treatment with barium hydroxide 3 Occurrence editAzetidine 2 carboxylic acid has been known since 1955 to be present in rhizomes and fresh foliage of certain plants It is known to occur in two species from the Asparagaceae Convallaria majalis lily of the valley and Polygonatum solomon s seal nbsp Lily of the ValleyAze is also found in numerous plants from the bean family Fabaceae and has also been detected in small quantities in table beets garden beets and sugar beets 4 Toxicity editIt has been shown that when Aze is misincorporated into proteins in place of proline Aze deters the growth of competing vegetation and poisons predators Other studies have shown effects of Aze resulting in a wide range of toxic and teratogenic disorders including in a range of malformations in various animal species including ducks hamsters mice and rabbits 2 Misincorporation of Aze into human proteins can alter collagen keratin hemoglobin and protein folding 5 However the lack of detailed toxicologic data and the need for more direct evidence about the damaging effects of the misincorporation of Aze on specific proteins are reasons why the toxicity of Aze to humans cannot be determined at this time 2 Molecular studies of human prolyl and alanyl tRNA synthetases suggest that Aze is incorporated in proteins as proline with toxic consequences in vivo 6 Even if Aze seems to fit into the active site of both tRNA synthetases due to its double mimicry effect of alanine and proline it is rejected by alanyl tRNA synthetases post transfer editing system 6 References edit Merck Index 12th Edition 6089 a b c Rubenstein E T McLaughlin R C Winant A Sanchez M Eckart K M Krasinska A Chien 2008 Azetidine 2 carboxylic Acid in the Food Chain Phytochemistry 70 1 1 5 doi 10 1016 j phytochem 2008 11 007 PMID 19101705 Fowden L 1956 Azetidine 2 carboxylic Acid a New Cyclic Imino Acid Occurring in Plants Biochemical Journal 64 2 323 331 doi 10 1042 bj0640323 PMC 1199734 PMID 13363844 Seigler David S 1998 Plant secondary metabolism Kluwer Academic p 222 ISBN 0 412 01981 7 Rubenstein E H Zhou K M Krasinska A Chien C H Becker 2006 Azetidine 2 carboxylic Acid in Garden Beets Phytochemistry 67 9 898 903 doi 10 1016 j phytochem 2006 01 028 PMID 16516254 a b Song Y Zhou H Vo MN Shi Y Nawaz MH Vargas Rodriguez O Diedrich JK Yates JR Kishi S Musier Forsyth K Schimmel P 22 December 2017 Double mimicry evades tRNA synthetase editing by toxic vegetable sourced non proteinogenic amino acid Nature Communications 8 1 2281 Bibcode 2017NatCo 8 2281S doi 10 1038 s41467 017 02201 z PMC 5741666 PMID 29273753 Retrieved from https en wikipedia org w index php title Azetidine 2 carboxylic acid amp oldid 1175822874, wikipedia, wiki, book, books, library,
