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

HRID 43232Notes

Reaction equation

HRID 43232 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-cd7b4602388849a2a28b067a224c6e61
Source dataset
uspto-grants-2013_09
Patent number
US08536305B2

Reaction notes

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