A derivative of L-proline with diverse biological activities
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L-Azetidine-2-carboxylic Acid

Item No. 33189

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S)-2-azetidinecarboxylic acid
CAS Number
2133-34-8
Synonyms
  • A2C
  • Aze
  • L-AZC
  • LACA
  • (S)-(–)-Azetidine-2-carboxylic Acid
Molecular Formula
C4H7NO2
Formula Weight
101.1
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: Slightly solublePBS (pH 7.2): 1 mg/ml
SMILES
OC([C@@H]1CCN1)=O
InChi Code
InChI=1S/C4H7NO2/c6-4(7)3-1-2-5-3/h3,5H,1-2H2,(H,6,7)/t3-/m0/s1
InChi Key
IADUEWIQBXOCDZ-VKHMYHEASA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 mg

    $41

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    250 mg

    $80

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    500 mg

    $119

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    1 g

    $157

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    Cayman Chemical
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    Product Description

    L-Azetidine-2-carboxylic acid is a non-proteinogenic amino acid derivative of L-proline that has been found in C. majalis and has diverse biological activities.1,2,3,4 It is toxic to a variety of bacteria, but the bacteria E. agglomerans and E. amnigenus metabolize it for use as a source of nitrogen. L-Azetidine-2-carboxylic acid induces misfolding of proteins when incorporated into the nascent polypeptide chain.1 It destabilizes the collagen triple helix and reduces the extracellular localization of collagen.2 L-Azetidine-2-carboxylic acid inhibits growth of type IV collagen-producing 450.1 murine mammary cancer cells in vitro (IC50 = 7.6 µg/ml) but is inactive in a 450.1 murine model of mammary cancer when administered at doses ranging from 12.5 to 200 mg/kg twice per day and induces liver toxicity at the highest dose.3 It is teratogenic to, and disrupts skeletal development in, hamster fetuses when administered to pregnant hamsters at a dose of 300 mg/kg on gestational day 11.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bach, T.M.H., and Takagi, H. Properties, metabolisms, and applications of L-proline analogues. Appl. Microbiol. Biotechnol. 97(15), 6623-6634 (2013).

    2. Zagari, A., Némethy, G., and Scheraga, H.A. The effect of the L-azetidine-2-carboxylic acid residue on protein conformation. I. Conformations of the residue and of dipeptides. Biopolymers 30(9-10), 951-959 (1990).

    3. Klohs, W.D., Steinkampf, R.W., Wicha, M.S., et al. Collagen-production inhibitors evaluated as antitumor agents. J. Natl. Cancer Inst. 75(2), 353-359 (1985).

    4. Joneja, M.G. Teratogenic effects of proline analogue L-azetidine-2-carboxylic acid in hamster fetuses. Teratology 23(3), 365-372 (1981).