| Identification | More | [Name]
L(+)-allo-Threonine | [CAS]
28954-12-3 | [Synonyms]
(2S 3S)-(+)-2-AMINO-3-HYDROXYBUTYRIC ACID
(2S,3S)-2-AMINO-3-HYDROXYBUTYRIC ACID
(2S,3S)-(+)-ALLO-THREONINE
ALLO-THREONINE
ALLO-THREONINE(TBU)-OH
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
L-ALLO-THREONINE
O-T-BUTYL-L-ALLO-THREONINE
allo-l-threonine
l-allothreonin
(2S
H-allo-Thr-OH(L-Allo-Threonine)
Allo-Thr-OH
(2S 3S)-(+)-2-AMINO-3-HYDROXYBUTYRIC ACID 99%
H-L-allo-Thr(tBu)-OH | [EINECS(EC#)]
249-327-2 | [Molecular Formula]
C4H9NO3 | [MDL Number]
MFCD00237373 | [Molecular Weight]
119.12 | [MOL File]
28954-12-3.mol |
| Chemical Properties | Back Directory | [Appearance]
white to off-white crystalline powder | [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. ]
Store at RT. | [solubility ]
Water (Slightly) | [form ]
Crystalline Powder | [pka]
pK1: 2.108(+1);pK2: 9.096(0) (25°C) | [color ]
White to off-white | [Optical Rotation]
[α]23/D +9.0°, c = 2 in H2O | [BRN ]
1721645 | [Major Application]
peptide synthesis | [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) |
| Hazard Information | Back Directory | [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]
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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