286338
DL-Isoserine
98%
Synonym(s):
(±)-3-Amino-2-hydroxypropionic acid
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About This Item
Linear Formula:
H2NCH2CH(OH)CO2H
CAS Number:
Molecular Weight:
105.09
Beilstein:
1721413
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
98%
form
powder
reaction suitability
reaction type: solution phase peptide synthesis
mp
235 °C (dec.) (lit.)
application(s)
peptide synthesis
SMILES string
NCC(O)C(O)=O
InChI
1S/C3H7NO3/c4-1-2(5)3(6)7/h2,5H,1,4H2,(H,6,7)
InChI key
BMYNFMYTOJXKLE-UHFFFAOYSA-N
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Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Mei-Xiang Wang et al.
The Journal of organic chemistry, 70(7), 2439-2444 (2005-03-25)
[reaction: see text] Biotransformations of a number of differently substituted and configured oxiranecarbonitriles using Rhodococcus sp. AJ270, a microbial whole-cell catalyst that contains nitrile hydratase/amidase, were studied. While almost all trans-configured 3-aryl-2-methyloxiranecarbonitriles and 2,3-dimethyl-3-phenyloxiranecarbonitrile were efficiently hydrated by the action
Jan Cz Dobrowolski et al.
Physical chemistry chemical physics : PCCP, 12(36), 10818-10830 (2010-07-10)
The IR low-temperature Ar and Kr matrix spectra of l-isoserine were registered for the first time and interpreted by means of the anharmonic DFT frequencies calculated at the B3LYP/aug-cc-pVTZ and B3LYP/aug-cc-pVDZ levels. 54 l-isoserine conformers were predicted to be stable
Microbial resolution of 2-hydroxy-3-nitropropionic acid for synthesis of optically active isoserine.
Y Yasohara et al.
Bioscience, biotechnology, and biochemistry, 65(5), 1258-1260 (2001-07-07)
The biocatalytic stereoselective hydrolysis of 2-hydroxy-3-nitropropionic acid esters was studied. Forty enzymes and three hundred microorganism strains were examined for their ability to hydrolyze ethyl 2-hydroxy-3-nitropropionic acid. Nocardia globerula IFO13150 gave n-butyl (R)-2-hydroxy-3-nitropropionate with a 92% enantiomeric excess (ee) and
Nagarjuna Palyam et al.
The Journal of organic chemistry, 74(11), 4390-4392 (2009-05-02)
We report a new protocol for synthesis of L-1-deoxymannojirimycin, L-1-deoxyidonojirimycin, and the N-isopropyl derivative of the latter compound from the readily available precursors (S)-isoserinal hydrate and 2-tert-butyl-2-methyl-1,3-dioxan-5-one. The key steps include diastereoselective proline-catalyzed syn aldol transformation and a reductive amination/cyclization.
B S Coller et al.
The Journal of biological chemistry, 268(28), 20741-20743 (1993-10-05)
Peptides containing sequences derived from the new NH2 terminus of the seven-transmembrane domain thrombin receptor after thrombin cleavage can activate platelets directly. We recently demonstrated that such peptides are readily cleaved and inactivated by plasma, serum, and endothelial cell-associated aminopeptidase
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