L(+)-allo-Threonine
L(+)-allo-Threonine Basic information
- Product Name:
- L(+)-allo-Threonine
- Synonyms:
-
- l-allothreonin
- O-T-BUTYL-L-ALLO-THREONINE
- H-ALLO-THR(BUT)-OH
- H-ALLO-THR-O
- H-ALLO-THR-OH
- H-ALLO-THR(TBU)-OH
- H-L-ALLO-THR-OH
- L(+)-ALLO-THREONINE
- CAS:
- 28954-12-3
- MF:
- C4H9NO3
- MW:
- 119.12
- EINECS:
- 249-327-2
- Product Categories:
-
- amino acid derivative
- Threonine [Thr, T]
- Amino Acids
- Mol File:
- 28954-12-3.mol
L(+)-allo-Threonine Chemical Properties
- Melting point:
- 272 °C (dec.)(lit.)
- alpha
- 9 º (c=2, H2O)
- Boiling point:
- 222.38°C (rough estimate)
- Density
- 1.3126 (rough estimate)
- refractive index
- 10 ° (C=5, H2O)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- Water (Slightly)
- pka
- pK1: 2.108(+1);pK2: 9.096(0) (25°C)
- form
- Crystalline Powder
- color
- White to off-white
- optical activity
- [α]23/D +9.0°, c = 2 in H2O
- BRN
- 1721645
- InChI
- InChI=1S/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)/t2-,3-/m0/s1
- InChIKey
- AYFVYJQAPQTCCC-HRFVKAFMSA-N
- SMILES
- C(O)(=O)[C@H]([C@@H](O)C)N
- CAS DataBase Reference
- 28954-12-3(CAS DataBase Reference)
Safety Information
- Safety Statements
- 24/25
- WGK Germany
- 3
- RTECS
- BA4055000
- HS Code
- 29225090
MSDS
- Language:English Provider:L(+)-allo-Threonine
- Language:English Provider:SigmaAldrich
- Language:English Provider:ACROS
L(+)-allo-Threonine Usage And Synthesis
Chemical Properties
white to off-white crystalline powder
Uses
L-allo-Threonine is a reactant used in the synthesis of an antibiotic, globomycin, and its congener, SF-1902 A5.
Definition
ChEBI: L-allothreonine is the L-enantiomer of allothreonine. It has a role as an Escherichia coli metabolite and a Saccharomyces cerevisiae metabolite. It is an allothreonine and a L-alpha-amino acid. It is an enantiomer of a D-allothreonine. It is a tautomer of a L-allothreonine zwitterion.
reaction suitability
reaction type: solution phase peptide synthesis
Synthesis
64420-00-4
72-19-5
The general procedure for the synthesis of L-threonine from 5-(1-hydroxyethyl)urea (CAS:64420-00-4) is as follows: in a 1 L autoclave, 144 g (1 mol) of 5-(1-hydroxyethyl)urea, 68 g of 25% ammonia, 110 g of calcium hydroxide (1.5 mol), 500 g of water, and 50 mL of n-butanol were added in sequence. The mixture was heated to 160-170°C and the reaction pressure was maintained at 1.5-2.0 MPa for 4 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the pH was adjusted by passing carbon dioxide to 8. The reaction mixture was filtered and the mother liquor was concentrated under reduced pressure. To the residue, 150 g of methanol was added and refluxed for 2 h. Crystals were precipitated after cooling. The crystals were collected by filtration, and the filter cake was dried under vacuum at 120°C for 4 h. 106.4 g of 2-amino-3-hydroxybutyric acid was obtained with a purity of 96% and a yield of 89.4%.
References
[1] Patent: CN104892521, 2018, B. Location in patent: Paragraph 0069; 0070
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L(+)-allo-Threonine(28954-12-3)Related Product Information
- 4-Aminobutyric acid
- ALTRENOGEST
- L-Threonine
- DL-4-Amino-3-hydroxybutyric acid
- 3-Hydroxybutyric acid
- Glycine
- L-Alanine
- H-PHG-OME HCL
- (S)-(+)-2-Amino-3-hydroxy-3-methylbutanoic acid
- POLYOXIN B
- (2S,3S)-2-Amino-3-methoxybutanoic acid
- TRANS-3-HYDROXY-L-PROLINE
- MYRIOCIN
- (2S,3S)-(2S,3R)-2-AMINO-3-HYDROXY-4-METHYLPENTANOIC ACID
- (2R,3R)-(-)-ALLO-THREONINE,D(-)-ALLO-THREONINE,D-ALLO-THREONINE
- DL-ALLO-THREONINE
- FMOC-ALLO-THR(TBU)-OH
- H-ALLO-THR(TBU)-OH,ALLO-THREONINE(TBU)-OH,O-T-BUTYL-L-ALLO-THREONINE