D(-)-allo-Threonine Chemical Properties

Melting point:

276 °C (dec.)(lit.)

alpha 

-33.5 º (c=1, 1N HCl 24 ºC)

Boiling point:

222.38°C (rough estimate)

Density 

1.3126 (rough estimate)

refractive index 

-10 ° (C=5, H2O)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Water (Slightly)

form 

Solid

pka

2.19±0.10(Predicted)

color 

White to Off-White

optical activity

-32.201°(C=0.01g/ml 1N HCl)

Water Solubility 

soluble

BRN 

1721644

InChIKey

AYFVYJQAPQTCCC-PWNYCUMCSA-N

CAS DataBase Reference

24830-94-2(CAS DataBase Reference)

NIST Chemistry Reference

D-allothreonine(24830-94-2)

Safety Information

Safety Statements 

24/25

WGK Germany 

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.

MSDS

• Language:English Provider:D(-)-allo-Threonine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

D(-)-allo-Threonine Usage And Synthesis

Description

D(-)-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. 

References

https://www.alfa.com/en/catalog/H27050/
http://www.sigmaaldrich.com/catalog/product/sigma/t9643?lang=en&region=US

Chemical Properties

white crystalline powder

Uses

They 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.

Definition

ChEBI: 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.

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 solution, 110 g of calcium hydroxide (1.5 mol), 500 g of deionized water and 50 mL of n-butanol were added in sequence. The reaction mixture was heated to 160-170°C and the reaction pressure was maintained at 1.5-2.0 MPa for 4 hours. After completion of the reaction, the reaction was cooled to room temperature, and carbon dioxide gas was introduced to adjust the pH of the reaction solution to 8. The insoluble material was removed by filtration, and the mother liquor was concentrated under reduced pressure. To the concentrated residue, 150 g of methanol was added and refluxed for 2 hours, then cooled to room temperature and crystals were precipitated. 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 (L-threonine) was obtained with a purity of 96% and a yield of 89.4%.

Purification Methods

Recrystallise D-allothreonine from aqueous EtOH or 50% EtOH. [Elliot J Chem Soc 62 1950, Birnbaum et al. J Biol Chem 194 455 1952, IR: Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 1961, Beilstein 4 IV 3170.]

References

[1] Patent: CN104892521, 2018, B. Location in patent: Paragraph 0069; 0070

D(-)-allo-Threonine(24830-94-2)Related Product Information

• 3-Hydroxybutyric acid
• DL-4-Amino-3-hydroxybutyric acid
• Glycine
• D-3-HYDROXYBUTYRATE DEHYDROGENASE
• L-Threonine
• 4-Aminobutyric acid
• ALTRENOGEST
• (2S,3S)-(+)-ALLO-THREONINE,ALLO-THREONINE,ALLO-THREONINE(TBU)-OH,L-ALLO-THREONINE,L(+)-ALLO-THREONINE,O-T-BUTYL-L-ALLO-THREONINE,H-allo-Thr-OH(L-Allo-Threonine)
• DL-ALLO-THREONINE
• D-beta-Hydroxyvaline
• (2R,3R)-2-Amino-3-methyloxybutanoic acid
• 3-hydroxybutyric acid
• Ammonia
• (2R,3R)/(2S,3S)-RACEMIC FMOC-BETA-HYDROXY-PHENYLALANINE
• DL-ERYTHRO-3-PHENYLSERINE
• FMOC-(R)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID
• ETHYL-D-ERYTHRO-SPHINGOSINATE HYDROCHLORIDE
• N-BOC-(R)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID