Hydrochloric Acid → 89319-60-8

HRID 552051Notes

Reaction equation

HRID 552051 reaction equation
[Na+].[C:2]([O:21][CH2:22][C@H:23]([CH2:44][O:45][P:46]([O:49][CH2:50][C@@H:51]([C:53]([O-:55])=[O:54])[NH2:52])([OH:48])=[O:47])[O:24]C(=O)CCCCCCC/C=C\CCCCCCCC)(=[O:20])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].C(O)C(N)(CO)CO.Cl.[Cl-].[K+].Cl>O>[C:2]([O:21][CH2:22][C@H:23]([CH2:44][O:45][P:46]([O:49][CH2:50][C@@H:51]([C:53]([OH:55])=[O:54])[NH2:52])([OH:48])=[O:47])[OH:24])(=[O:20])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4873Potassium ChlorideHCID 93573Tromethamine hydrochlorideHCID 88111507HCID 88111507, compound

Product 1

HCID 954709989319-60-8

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After 1,2-dioleoyl-sn-glycero-3-phospho-L-serine sodium salt (SIGMA, P1060) (85 mg) was dissolved in distilled water (25 ml), 200 mM Tris-HCl buffer (pH 8.0) (1.5 ml) and 100 mM potassium chloride (1.5 ml) were added to the solution, and phospholipase A2 (0.3 ml) (10 mg/ml, 5 mM sodium acetate buffer (pH 5.0)) was further added thereto. The mixture was reacted at room temperature for 20 hours, and the pH was rendered 2 to 3 with 5M hydrochloric acid to terminate the reaction. After the reaction solution was concentrated to dryness, the residue was dissolved in a chloroform-methanol solvent mixture and the solution was adsorbed on silica gel column chromatography. Elution was performed with a chloroform-methanol solvent mixture to give 1-oleoyl-sn-glycero-3-phospho-L-serine. Subsequently, 1-oleoyl-sn-glycero-3-phospho-L-serine was catalytically hydrogenated with gaseous tritium (3H2) in the presence of palladium, in accordance with publicly known methods (e.g., the methods described in R. F. Glascock, Isotopic Gas Analysis for Biochemists, 227, Academic Press, New York, 1954) to introduce tritium into the double bond. Thus, the objective product, 1-[9,10-3H2]-stearoyl-sn-glycero-3-phospho-L-serine was obtained.

Workup

  1. additionwas further added
  2. customThe mixture was reacted at room temperature for 20 hours
  3. customto terminate
  4. customthe reaction
  5. concentrationAfter the reaction solution was concentrated to dryness
  6. dissolutionthe residue was dissolved in a chloroform-methanol solvent mixture
  7. washElution

Sources & evidence

ORD record
ord-030d34d530384bac9fb53c943903ea51
Source dataset
uspto-grants-2011_05
Patent number
US07951548B2

Reaction notes

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