L-Isoserine Chemical Properties

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

InChIKey

BMYNFMYTOJXKLE-REOHCLBHSA-N

SMILES

C(O)(=O)[C@@H](O)CN

CAS DataBase Reference

632-13-3(CAS DataBase Reference)

Safety Information

WGK Germany 

3

F 

10-21

HS Code 

2922500090

MSDS

• Language:English Provider:SigmaAldrich

L-Isoserine Usage And Synthesis

Uses

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.

L-Isoserine(632-13-3)Related Product Information

• DL-2-AMINOPROPIONIC ANHYDRIDE
• DL-ISOSERINE,DL-ISOSERINE 99+%
• (2r,3s)-n-tert-butoxycarbonyl-3-phenyl-isoserine methyl ester,METHYL (2R,3S)-N-BOC-3-PHENYL ISOSERINE
• FMOC-DL-ISOSERINE,N-BETA-(9-FLUORENYLMETHOXYCARBONYL)-DL-ISOSERINE
• (S)-IsoserineL-Isoserine,(R)-ISOSERINE
• ISOSERINE,
• N-BETA-T-BUTOXYCARBONYL-DL-ISOSERINE
• N-(T-BOC)-3-PHENYL ISOSERINE ETHYL ESTER
• D-Isoserine
• Isoserine, N,N-dimethyl- (6CI)
• FMOC-ISOSERINE
• 2R,3S-N-BENZOYLPHENYL ISOSERINE ( TAXOL SIDE CHAI
• Isoserine, N-glycyl- (3CI)
• BOC-ISOSERINE
• ISOSERINE
• BOC-ISOSERINE,
• Isoserine, N-2-pyridyl-, methyl ester, DL- (6CI)
• N-boca mino phenyl isoserine