11542
L-Azetidine-2-carboxylic acid
purum, ≥98.0% (NT)
Synonym(s):
(S)-Azetidine-2-carboxylic acid
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About This Item
Empirical Formula (Hill Notation):
C4H7NO2
CAS Number:
Molecular Weight:
101.10
EC Number:
218-362-5
UNSPSC Code:
12352200
PubChem Substance ID:
Beilstein/REAXYS Number:
80680
MDL number:
grade
purum
assay
≥98.0% (NT)
optical activity
[α]20/D −123±2°, c = 4% in H2O
mp
~215 °C (dec.)
SMILES string
OC(=O)[C@@H]1CCN1
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
Biochem/physiol Actions
L-Azetidine-2-carboxylic acid is an inhibitor of collagen synthesis that is anti-angiogenic.
L-Azetidine-2-carboxylic acid is an inhibitor of collagen synthesis that is anti-angiogenic. It is a four-membered ring analog of L-proline that causes protein misconstruction when incorporated instead of proline.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Other Notes
Preparation of mugineic acid; 4-Oxidation to the corresponding lactam
Storage Class
13 - Non Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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Y. Hamada et al.
The Journal of Organic Chemistry, 51, 5489-5489 (1986)
K. Tanaka et al.
Heterocycles, 24, 2539-2539 (1986)
Kaoru Iinoya et al.
Biotechnology and bioengineering, 103(2), 341-352 (2009-01-27)
The budding yeast Saccharomyces cerevisiae Sigma1278b has the MPR1 gene, which confers resistance to the proline analogue azetidine-2-carboxylate (AZC). This gene encodes an N-acetyltransferase Mpr1 that detoxifies AZC, and the homologous genes have been found in many yeasts. Recently, we
B A Kirby et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 14(9), 5687-5693 (1994-09-01)
A68, or PHF-tau, is an abnormally phosphorylated form of the microtubule-associated protein tau, which is a primary protein constituent of paired helical filaments (PHFs) and, ultimately, of Alzheimer's disease-associated neurofibrillary tangles (NFTs). Previously, we have shown that in heat-shocked neuronal
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