D-Homoserine Chemical Properties

Melting point:

205 °C (dec.) (lit.)

alpha 

9 º ((c=5, H2O))

Boiling point:

368.7±32.0 °C(Predicted)

Density 

1.312±0.06 g/cm3(Predicted)

refractive index 

8.0 ° (C=2, H2O)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

pka

2.21±0.10(Predicted)

form 

powder to crystal

color 

White to Orange to Green

Water Solubility 

Soluble

BRN 

1721680

InChI

InChI=1S/C4H9NO3/c5-3(1-2-6)4(7)8/h3,6H,1-2,5H2,(H,7,8)/t3-/m1/s1

InChIKey

UKAUYVFTDYCKQA-GSVOUGTGSA-N

SMILES

C(O)(=O)[C@@H](CCO)N

LogP

-1.289 (est)

CAS DataBase Reference

6027-21-0(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

F 

10

HS Code 

29225090

MSDS

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

D-Homoserine Usage And Synthesis

Chemical Properties

White to lightbyellow crystalline powder

Uses

peptide synthesis

Definition

ChEBI: The D-enantiomer of homoserine.

Biochem/physiol Actions

D-Homoserine is used for the synthesis of bacterial polysaccharids such as the O-antigen of Acinetobacter lwoffii EK30A. D-Homoserine is used to produce atypical serine protease(s) for mechanism studies.

Synthesis

The general procedure for the synthesis of D-homoserine from D-methionine was as follows: D-methionine (1) (25.0 g, 167.5 mmol, 1 eq.) was suspended in a mixed H2O/MeOH solvent (466 mL/66 mL) according to the literature method, followed by the addition of methyl iodide (25.2 mL, 405.4 mmol, 2.4 eq.). The resulting suspension was stirred vigorously at room temperature for 48 hours. Upon completion of the reaction, the volume of the reaction mixture was concentrated to one-third of the original volume by vacuum evaporation, while the excess methyl iodide was removed. To the remaining reaction mixture was added water (155 mL) followed by NaHCO3 (14.07 g, 167.5 mmol, 1 equiv). The resulting solution was refluxed for 15 hours and then cooled to room temperature. The solvent was removed under vacuum to give a thick syrupy substance. The syrupy substance was dissolved in water (45 mL) under heating, followed by sequential addition of acetone (90 mL) and ethanol (1000 mL), and a white solid precipitate was observed. The precipitate was filtered and dried under vacuum to give a white solid of the target product D-homoserine (2). Yield: 9.9 g (83 mmol, 50% yield). Melting point: 202°C. 1H NMR (300 MHz, D2O): δ = 1.92-1.78 (m, 1H, 3-CH), 2.09-2.92 (m, 1H, 3-CH), 3.65-3.58 (m, 2H, 4-CH2), 3.68 (dd, 3JH,H = 4.8, 3JH,H = 7.5 Hz, 1H, 2-CH ).13C NMR (75 MHz, D2O): δ = 32.1 (s, 3-C), 53.3 (s, 2-C), 58.5 (s, 4-C), 174.5 (s, 1-C).HRMS (ESI+, MeOH): m/z = 142.0468 [M + Na]+ with a calculated value of 142.0475 for C4H9NO3Na.

References

[1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 19, p. 5168 - 5181
[2] Tetrahedron, 1988, vol. 44, # 2, p. 637 - 642

D-Homoserine(6027-21-0)Related Product Information

• L-CYCLOSERINE
• L-Threonine
• 4-Aminobutyric acid
• DL-Serine
• 4-Cyanophenol
• L-ALPHA-PHOSPHATIDYLSERINES, BRAIN, BOVINE
• Glycine
• 6-Aminocaproic acid
• MCPB
• D-Glucosamic acid
• D-ASPARTIC ACID(OBZL)-OBZL P-TOSYLATE
• cis-4-Hydroxy-D-proline
• H-D-ASP-OBZL
• D-ASPARTIC ACID DIMETHYL ESTER HYDROCHLORIDE
• D-Aspartic acid
• Boc-D-aspartic acid 4-cyslohexyl ester
• trans-4-Hydroxy-D-proline
• H-HOMOSERINE,HOMOSERINE,HOMOSERINE-L