(2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid;(2S)-2-aminopentanedioic acid;(2S)-2-aminopropanoic acid;(2S)-2,6-diaminohexanoic acid → Glatiramer (acetate)

HRID 43231Notes

Reaction equation

HRID 43231 reaction equation
[CH3:1][C@H:2]([NH2:6])[C:3]([OH:5])=[O:4].[CH:7]1[C:12]([CH2:13][C@H:14]([NH2:18])[C:15]([OH:17])=[O:16])=[CH:11][CH:10]=[C:9]([OH:19])[CH:8]=1.[CH2:20]([CH2:24][C@H:25]([NH2:29])[C:26]([OH:28])=[O:27])[CH2:21][CH2:22][NH2:23].[CH2:30]([C@H:35]([NH2:39])[C:36]([OH:38])=[O:37])[CH2:31][C:32]([OH:34])=[O:33]>C([O-])(=O)C.[NH4+]>[CH3:1][C@H:2]([NH2:6])[C:3]([OH:5])=[O:4].[CH3:14][C:15]([OH:17])=[O:16].[CH:7]1[C:12]([CH2:13][C@H:14]([NH2:18])[C:15]([OH:17])=[O:16])=[CH:11][CH:10]=[C:9]([OH:19])[CH:8]=1.[CH2:20]([CH2:24][C@H:25]([NH2:29])[C:26]([OH:28])=[O:27])[CH2:21][CH2:22][NH2:23].[CH2:30]([C@H:35]([NH2:39])[C:36]([OH:38])=[O:37])[CH2:31][C:32]([OH:34])=[O:33]

Participants

3

Reactant 1

HCID 65370(2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid;(2S)-2-aminopentanedioic acid;(2S)-2-aminopropanoic acid;(2S)-2,6-diaminohexanoic acid

Product 1

HCID 3081884Glatiramer (acetate)

Reagents, catalysts & solvents 1

HCID 517165Ammonium AcetateSolvent2×

Procedure

The glatiramer as extract of pH=6 prepared in Example 23 is concentrated in vacuo to dryness and subjected to chromatographic separation. A column for gel filtration, FRACTOGEL TSK HW55 (600×26 mm) is prepared in a Superformance 26 Merck cartridge according to the manufacturer's instructions. The column is equilibrated with 0.2 M ammonium acetate buffer pH 5.0, 30 mL of glatiramer free base solution samples (20 mg/mL, in 0.2 M ammonium acetate pH 5.0) are loaded on the column and fractions are collected. A fraction having an average molecular weight of 7-10 kDa is isolated.

Workup

  1. extractionThe glatiramer as extract of pH=6
  2. customprepared in Example 23
  3. concentrationis concentrated in vacuo to dryness
  4. customsubjected to chromatographic separation
  5. filtrationA column for gel filtration, FRACTOGEL TSK
  6. custom(600×26 mm) is prepared in a Superformance 26 Merck cartridge
  7. customare collected
  8. customis isolated

Sources & evidence

ORD record
ord-8d245810fd944240a9739c51f064fb5e
Source dataset
uspto-grants-2013_09
Patent number
US08536305B2

Reaction notes

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