Azetidine-2-carboxylic acid

Source: Wikipedia, the free encyclopedia.
Azetidine-2-carboxylic acid[1]
Names
IUPAC name
Azetidine-2-carboxylic acid
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.016.693 Edit this at Wikidata
EC Number
  • 218-362-5
IUPHAR/BPS
KEGG
UNII
  • InChI=1S/C4H7NO2/c6-4(7)3-1-2-5-3/h3,5H,1-2H2,(H,6,7)/t3-/m0/s1 checkY
    Key: IADUEWIQBXOCDZ-VKHMYHEASA-N checkY
  • InChI=1/C4H7NO2/c6-4(7)3-1-2-5-3/h3,5H,1-2H2,(H,6,7)/t3-/m0/s1
    Key: IADUEWIQBXOCDZ-VKHMYHEABQ
  • O=C(O)[C@H]1NCC1
Properties
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)
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 checkY☒N ?)

Azetidine-2-carboxylic acid (abbreviated Aze or Azc) is a plant

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.

Synthesis

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]

Occurrence

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

Lily of the Valley

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]

Toxicity

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]

References

  1. ^ Merck Index, 12th Edition, 6089.
  2. ^
    PMID 19101705
    .
  3. PMID 13363844
    .
  4. ISBN 0-412-01981-7
    .
  5. PMID 16516254
    .
  6. ^
    PMID 29273753
    .
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