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HomeProduct name listL-Isoserine

L-Isoserine

Synonym(s):(S)-2-Hydroxy-β-alanine;(S)-3-Amino-2-hydroxypropionic acid

L-Isoserine Structural

What is L-Isoserine?

The Uses of L-Isoserine

It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuffs.

Biological Activity

Research has found that L-isoserine showed the ability to inhibit Aminopeptidase N (APN) at a half-maximal inhibitory concentration (IC50 ) value of 563 μM, which could serve as a new lead compound for further chemical modification and optimization. In addition, it has been reported that L-isoserine-L-leucine dipeptide shows moderate aminopeptidase B inhibitory activity (IC50 of 140 μM). This evidence indicates that the incorporation of an amino acid to L-isoserine may contribute to its inhibitory activity against APN.  L-isoserine induces long-lasting effects by increasing the expression of GAT3 (glial GABA transporte) in peri-infarct regions[1-2].

References

[1] Yang K , et al. Synthesis of a novel series of L-isoserine derivatives as aminopeptidase N inhibitors. Journal of Enzyme inhibition and Medicinal Chemistry, 2011; 27: 302-310.
[2] Lie M , et al. GAT3 selective substrate l-isoserine upregulates GAT3 expression and increases functional recovery after a focal ischemic stroke in mice. Journal of Cerebral Blood Flow & Metabolism, 2017; 39.

Properties of L-Isoserine

Melting point: 199~201℃
Boiling point: 386.6±27.0 °C(Predicted)
Density  1.415±0.06 g/cm3(Predicted)
storage temp.  under inert gas (nitrogen or Argon) at 2-8°C
form  powder to crystal
pka pK1:2.72(+1);pK2:9.25(0) (25°C,μ=0.16)
color  White to Almost white
Water Solubility  Slightly soluble in water.
Sensitive  Moisture Sensitive
InChI InChI=1S/C3H7NO3/c4-1-2(5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1
CAS DataBase Reference 632-13-3(CAS DataBase Reference)

Safety information for L-Isoserine

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.

Computed Descriptors for L-Isoserine

InChIKey BMYNFMYTOJXKLE-REOHCLBHSA-N
SMILES C(O)(=O)[C@@H](O)CN

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