D-LYSINE METHYL ESTER DIHYDROCHLORIDE Chemical Properties

Melting point:

205 °C

refractive index 

-17 ° (C=5, H2O)

storage temp. 

Inert atmosphere,Room Temperature

Water Solubility 

Soluble in water

solubility 

Methanol (Slightly), Water (Slightly)

form 

powder to crystal

color 

White to Almost white

Stability:

Hygroscopic

CAS DataBase Reference

67396-08-1

Safety Information

HS Code 

2922.41.0090

D-LYSINE METHYL ESTER DIHYDROCHLORIDE Usage And Synthesis

Uses

D-Lysine Methyl Ester is a protected form of D-Lysine (L468930). D-Lysine is the unnatural isomer of L-Lysine (L468895) that has the ability to reduce non-enzymatic glycation in vitro. D-Lysine also exists as polypeptide chains of poly-D-lysine, a nonspecific adhesion-promoting molecule that has the potential to be a polymeric drug carrier.

Synthesis

L-lysine hydrochloride (2, 5.00 g, 27.4 mmol, 1.0 eq.) and methanol (30 mL, 0.9 M) were added to a round bottom flask. The suspension was heated to reflux to completely dissolve the solid. Thionyl chloride (2.59 mL, 35.6 mmol, 1.3 eq.) was added slowly and dropwise over 15 min. The reaction mixture was kept under reflux conditions for 17 hours. Removal of most of the volatiles (~25 mL) by distillation followed by azeotropic removal of the remaining volatiles by toluene under reduced pressure afforded pure lysine methyl ester dihydrochloride (3, quantitative mass recovery, white solid), which was used directly in the next step of the reaction without further purification. The product was analyzed and the data were consistent with those reported in the literature.

References

[1] Tetrahedron Letters, 2016, vol. 57, # 4, p. 502 - 504
[2] Journal of Medicinal Chemistry, 2002, vol. 45, # 17, p. 3669 - 3683
[3] Heterocycles, 2017, vol. 94, # 5, p. 964 - 978
[4] Journal of Polymer Science, Part A: Polymer Chemistry, 2015, vol. 53, # 17, p. 2036 - 2049
[5] Molecules, 2016, vol. 21, # 1,

D-LYSINE METHYL ESTER DIHYDROCHLORIDE(67396-08-1)Related Product Information

• D-Lysine
• D-Lysine hydrochloride
• L-Tyrosine Ethyl Ester Hydrochloride
• D-Leucine methyl ester hydrochloride
• H-D-TYR-OME HCL
• METHYL D-HOMOALANINATE HCL
• (S)-3-Amino-3-phenyl propionic acid methylester HCl
• Methyl 4-aminobutyrate hydrochloride
• D-Ornithine monohydrochloride
• L-Valine methyl ester hydrochloride
• D-allo-Isoleucine Ethyl Ester Hydrochloride
• 2-AMINO-2-METHYL-BUTYRIC ACID METHYL ESTER HYDROCHLORIDE
• H-D-ALLO-THR-OME HCL
• ETHYL 4-AMINOBUTYRATE HYDROCHLORIDE
• H-ABU-OME HCL
• N-Benzylglycine ethyl ester
• H-D-LYS(Z)-OH
• H-D-LYS(Z)-OBZL HCL