| Identification | More | [Name]
L-Isoserine | [CAS]
632-13-3 | [Synonyms]
L-ISOSERINE
(S)-2-HYDROXY-B-ALANINE
(S)-2-HYDROXY-BETA-ALANINE
(S)-3-AMINO-2-HYDROXYPROPIONIC ACID
(S)-ISOSERINE
(s)-2-hydroxy-β-alanine
(S)-LSOSERINE
(2S)-3-AMINO-2-HYDROXY-PROPANOIC ACID
(S)-2-Hydroxy-β-alanine, (S)-3-Amino-2-hydroxypropionic acid
(-)-3-Amino-L-lactic acid
(S)-3-Amino-2-hydroxypropanoic acid | [Molecular Formula]
C3H7NO3 | [MDL Number]
MFCD03428326 | [Molecular Weight]
105.09 | [MOL File]
632-13-3.mol |
| Chemical Properties | Back Directory | [Melting point ]
199~201℃ | [Boiling point ]
386.6±27.0 °C(Predicted) | [density ]
1.415±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,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 | [Optical Rotation]
Consistent with structure | [Water Solubility ]
Slightly soluble in water. | [Sensitive ]
Moisture Sensitive | [Major Application]
peptide synthesis | [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) |
| Hazard Information | Back Directory | [Uses]
It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuffs. | [reaction suitability]
reaction type: solution phase peptide synthesis | [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. |
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