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

HRID 1026377Notes

Reaction equation

HRID 1026377 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 acetate solution prepared in Example 31 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. concentrationThe glatiramer acetate solution prepared in Example 31 is concentrated in vacuo to dryness
  2. customsubjected to chromatographic separation
  3. filtrationA column for gel filtration, FRACTOGEL TSK
  4. custom(600×26 mm) is prepared in a Superformance 26 Merck cartridge
  5. customare collected
  6. customis isolated

Sources & evidence

ORD record
ord-3a3506b07dc5430aa9fbf724c33f4b67
Source dataset
uspto-grants-2014_05
Patent number
US08729229B2

Reaction notes

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