Identification | Back Directory | [Name]
D-LYSINE METHYL ESTER DIHYDROCHLORIDE | [CAS]
67396-08-1 | [Synonyms]
D-Lys-OMe 2HCl D-LysineMethylEsterDihydrochloride> METHYL 2,6-DIAMINOHEXANOATE DIHYDROCHLORIDE (R)-Methyl 2,6-diaminohexanoate dihydrochloride D-LYSINE METHYL ESTER DIHYDROCHLORIDE USP/EP/BP methyl (2R)-2,6-diaminohexanoate dihydrochloride D-Lysine Methyl Ester Dihydrochloride | [Molecular Formula]
C7H16N2O2.2HCl | [MDL Number]
MFCD00039067 | [MOL File]
67396-08-1.mol |
Chemical Properties | Back Directory | [Melting point ]
205 °C | [refractive index ]
-17 ° (C=5, H2O) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
Methanol (Slightly), Water (Slightly) | [Water Solubility ]
Soluble in water | [form ]
powder to crystal | [color ]
White to Almost white | [Stability:]
Hygroscopic | [CAS DataBase Reference]
67396-08-1 |
Hazard Information | Back Directory | [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, |
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