D-Homoserine

White to lightbyellow crystalline powder

D-homoserine is the D-enantiomer of homoserine. It is a homoserine and a D-alpha-amino acid. It is an enantiomer of a L-homoserine. It is a tautomer of a D-homoserine zwitterion.

According to a literature procedure, 19D-methionine (1) (25.0 g, 167.5 mmol, 1 equiv) was suspended in H2O/MeOH (466 mL/66 mL), and methyl iodide (25.2 mL, 405.4 mmol, 2.4 equiv) wasadded. The resulting suspension was stirred vigorously at roomtemperature for 48 h. Then the volume of the reaction mixturewas reduced to one-third by evaporation under vacuo and alongwith this, excess of methyl iodide was also removed. Water(155 mL) was added to the remaining reaction mixture followedby NaHCO3 (14.07 g, 167.5 mmol, 1 equiv). The resulting solutionwas refluxed for 15 h and cooled to room temperature. Solventwas removed under vacuo to yield thick syrup. This was dissolvedin water (45 mL) with heating. Addition of acetone (90 mL) followedby ethanol (1000 mL) resulted in the precipitation of a whitesolid, which was filtered and dried under vacuum to give 2 aswhite solid. Yield: 9.9 g (83 mmol, 50percent). Mp 202 C. 1H NMR(300 MHz, D2O): d = 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): d = 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]+ calcd for C4H9NO3Na+ 142.0475.According to a literature procedure, 19D-methionine (1) (25.0 g, 167.5 mmol, 1 equiv) was suspended in H2O/MeOH (466 mL/66 mL), and methyl iodide (25.2 mL, 405.4 mmol, 2.4 equiv) wasadded. The resulting suspension was stirred vigorously at roomtemperature for 48 h. Then the volume of the reaction mixturewas reduced to one-third by evaporation under vacuo and alongwith this, excess of methyl iodide was also removed. Water(155 mL) was added to the remaining reaction mixture followedby NaHCO3 (14.07 g, 167.5 mmol, 1 equiv). The resulting solutionwas refluxed for 15 h and cooled to room temperature. Solventwas removed under vacuo to yield thick syrup. This was dissolvedin water (45 mL) with heating. Addition of acetone (90 mL) followedby ethanol (1000 mL) resulted in the precipitation of a whitesolid, which was filtered and dried under vacuum to give 2 aswhite solid. Yield: 9.9 g (83 mmol, 50percent). Mp 202 C. 1H NMR(300 MHz, D2O): d = 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): d = 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]+ calcd for C4H9NO3Na+ 142.0475.

Molecular Weight:119.12
XLogP3:-4.4
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:119.058243149
Monoisotopic Mass:119.058243149
Topological Polar Surface Area:83.6
Heavy Atom Count:8
Complexity:83.4
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes