(2R,3R)-2-azaniumyl-3-hydroxybutanoate
Basic information
- CAS
24830-94-2- Standard SMILES
C[C@@H](O)[C@@H]([NH3+])C(=O)[O-]- InChIKey
AYFVYJQAPQTCCC-PWNYCUMCSA-N- Molecular formula
- C4H9NO3
- Average molar mass
- 119.12 g/mol
- Monoisotopic mass
- 119.05824315
Overview
D-allothreonine zwitterion is a D-alpha-amino acid zwitterion that is D-allothreonine in which a proton has been transferred from the carboxy group to the amino group. It is the major species at pH 7.3. It is a tautomer of a D-allothreonine.
Names & identifiers
- Preferred name
- (2R,3R)-2-azaniumyl-3-hydroxybutanoate
- IUPAC
- (2R,3R)-2-azaniumyl-3-hydroxybutanoate
- English name
- D(-)-allo-Threonine
- Molecular formula
- C4H9NO3
- Molecular weight
- 119.12
Names & synonyms
(2R,3R)-2-azaniumyl-3-hydroxybutanoateD-allothreonine zwitterionCHEBI:58645H-D-ALLO-THR-OHD-ALLO-THREONINE(2R,3R)-2-Amino-3-hydroxybutanoic acid(2R,3R)-2-AMINO-3-HYDROXYBUTYRIC ACIDd-allothreoninallo-D-ThreonineAllothreonine, D-(r)-allothreonineD(-)-ALLO-THREONINE
Show more names
D-Allothreonine >
Database identifiers
- CAS
24830-94-2、632-20-2- PubChem CID
- 6971050
- ChEBI
CHEBI:58645
Properties
Computed structural properties
- XLogP
- -2.3
- Topological polar surface area
- 88 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 87.8
Physicochemical properties
- Melting point
- 276 °C · 276 °C (dec.)(lit.)
- alpha
- -33.5 · -33.5 º (c=1, 1N HCl 24 ºC)
- Boiling point
- 222.38 °C · 222.38°C (rough estimate)
- Density
- 1.3126 · 1.3126 (rough estimate)
- refractive index
- -10 ° · -10 ° (C=5, H2O)
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
- solubility
- Water (Slightly)
- form
- Solid
- pka
- 2.19 · 2.19±0.10(Predicted)
- color
- White to Off-White
- optical activity
- -32.201 ° · -32.201°(C=0.01g/ml 1N HCl)
- Water Solubility
- soluble
- BRN
- 1721644 · 1721644
- InChIKey
- AYFVYJQAPQTCCC-PWNYCUMCSA-N
- CAS DataBase Reference
- 24830 · 24830-94-2(CAS DataBase Reference)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- rtecs
- BA4050000
- hs_code
- 29225090
- Toxicity
- rat,LD50,intraperitoneal,6910mg/kg (6910mg/kg),BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)LUNGS, THORAX, OR RESPIRATION: DYSPNEA,Archives of Biochemistry and Biophysics. Vol. 64, Pg. 319, 1956.
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 24/25
- Hazard statements
- H315-H319
- Precautionary statements
- P305+P351+P338
Chemistry & industry
Applications
DescriptionD(-)-allo-Threonine is an isomer of threonine. It is found as a constituent of an increasing group of biologically active peptides. Stereocontrolled syntheses of chiral and racemic key intermediates to thienamycin can be achieved from d-allo-threonine and trans-crotonic acid.
UsesThey are found as constituents of an increasing group of biologically active peptides. Stereocontrolled syntheses of chiral and racemic key intermediates to thienamycin from d-allo-threonine and trans-crotonic acid.
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: D-allothreonine is the D-enantiomer of allothreonine. It occurs as a component of peptido-lipids in certain bacteria. It has a role as a bacterial metabolite. It is an allothreonine and a D-alpha-amino acid. It is an enantiomer of a L-allothreonine. It is a tautomer of a D-allothreonine zwitterion.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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