D-Threonine Chemical Properties

Melting point:

274 °C

alpha 

28 º (c=6, water)

Boiling point:

222.38°C (rough estimate)

Density 

1.3126 (rough estimate)

refractive index 

28 ° (C=3, H2O)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

H2O: soluble

pka

2.19±0.10(Predicted)

form 

Crystals or Crystalline Powder

color 

White

Water Solubility 

soluble

Merck 

9380

BRN 

1721643

InChIKey

AYFVYJQAPQTCCC-STHAYSLISA-N

CAS DataBase Reference

632-20-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-37/39-26

WGK Germany 

3

RTECS 

XO8580000

HS Code 

29225000

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

D-Threonine Usage And Synthesis

Description

D-threonine is the D-form of threonine, which is a kind of amino acids. It can be used for the preparation of enantiomerically pure 1, 3-butanediol. It is also used as the intermediate during the preparation of chiral compounds such as antibiotics. D-threonine is an effective chiral pool reagent which contains an extra stereo-center. For example, people has recently used it as the starting material for total synthesis of protected legionaminic acid.

Chemical Properties

white crystalline powder or crystals

Uses

D-Threonine is the unnatural isomer of L-Threonine (T405500) and is known to inhibit growth and cell wall synthesis of Mycobacterium smegmatis. D-Threonine is also used as a synthetic intermediate for the production of chiral antibiotics. It is a steroisomer of the proteinogenic amino acid L-threonine. It has the potential to treat hypostatic leg ulceration.

Definition

ChEBI: D-threonine is an optically active form of threonine having D-configuration. It has a role as a Saccharomyces cerevisiae metabolite. It is a threonine and a D-alpha-amino acid. It is a conjugate base of a D-threoninium. It is a conjugate acid of a D-threoninate. It is an enantiomer of a L-threonine. It is a tautomer of a D-threonine zwitterion.

Application

D-Threonine is a steroisomer of the proteinogenic amino acid L-threonine. D-threonine is an important organic chiral source, mainly used in the fields of chiral drugs, chiral additives, chiral auxiliaries, etc., as a chiral source for chiral synthesis in the pharmaceutical industry. As an optically active organic acid, it has an irreplaceable role in the asymmetric synthesis of certain chiral compounds. It is mainly used to produce new broad-spectrum antibiotics, D-threonine, and threonine protection in peptide synthesis.

benefits

Threonine, pronounced three-uh-neen is one of nine essential amino acids your body needs to function properly. Aiding in maintaining healthy skin, teeth, collagen, elastin, and muscle tissue, it also helps with digestion, metabolism and preventing fat buildup in the liver. Threonine has been used to treat intestinal disorders and indigestion and can be used to help those suffering from depression and anxiety. Recently it has been shown to have promising sleep-promoting effects, which may prove helpful for those who have insomnia and other sleep disorders

General Description

D-Threonine is sweet and toxic in nature.It acts as an inhibitor of L-threonine dehydratase. L-Threonine orientations differ from D-Threonine, specifically in their angles. The L-Threonine tended to self assemble with other L-Threonine molecules while D-Threonine tended to self assemble with other D-Threonine molecules.

References

https://www.alfa.com/zh-cn/catalog/B21177/
Ikemi, Masahisa, et al. "D-Threonine Aldolase and Its Application to D -β-Hydroxy-£-Amino Acid Synthesis." (1992).
Paek SM, et al. "Recent Advances in Substrate-Controlled Asymmetric Induction Derived from Chiral Pool α-Amino Acids for Natural Product Synthesis." Molecules 21.7(2016):951.

D-Threonine (632-20-2)Related Product Information

• 3-Hydroxybutyric acid
• Glycine
• 6-Aminocaproic acid
• DL-4-Amino-3-hydroxybutyric acid
• ALTRENOGEST
• 4-Aminobutyric acid
• Tris(hydroxymethyl)aminomethane
• 3-Aminopyridine
• 3-Aminophenol
• DL-Threonine
• FMOC-O-TERT-BUTYL-D-THREONINE,FMOC-O-T-BUTYL-D-THREONINE,FMOC-D-THREONINE(TBU)-OH
• Z-D-THR-OH
• (2R,3S)-(-)-2-Amino-3-hydroxy-4-methylpentanoic acid
• L-Threonine
• N-(tert-Butoxycarbonyl)-O-benzyl-D-threonine
• D-beta-Hydroxyvaline
• BOC-D-THR-OH
• D-Glucosamic acid