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

HRID 388197Notes

Reaction equation

HRID 388197 reaction equation
[CH3:1][C@H:2]([NH2:6])[C:3]([OH:5])=[O:4].CC(O)=O.[CH:11]1[C:16]([CH2:17][C@H:18]([NH2:22])[C:19]([OH:21])=[O:20])=[CH:15][CH:14]=[C:13]([OH:23])[CH:12]=1.[CH2:24]([CH2:28][C@H:29]([NH2:33])[C:30]([OH:32])=[O:31])[CH2:25][CH2:26][NH2:27].[CH2:34]([C@H:39]([NH2:43])[C:40]([OH:42])=[O:41])[CH2:35][C:36]([OH:38])=[O:37]>B([O-])([O-])[O-]>[CH3:1][C@H:2]([NH2:6])[C:3]([OH:5])=[O:4].[CH:11]1[C:16]([CH2:17][C@H:18]([NH2:22])[C:19]([OH:21])=[O:20])=[CH:15][CH:14]=[C:13]([OH:23])[CH:12]=1.[CH2:24]([CH2:28][C@H:29]([NH2:33])[C:30]([OH:32])=[O:31])[CH2:25][CH2:26][NH2:27].[CH2:34]([C@H:39]([NH2:43])[C:40]([OH:42])=[O:41])[CH2:35][C:36]([OH:38])=[O:37]

Participants

3

Reactant 1

HCID 3081884Glatiramer (acetate)2×

Product 1

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

Reagents, catalysts & solvents 1

HCID 26574BorateSolvent2×

Procedure

4.8 mg of glatiramer acetate (potency 83% as base for reference standard) were weighed into a 10 ml volumetric flask. Approximately 7 ml of 0.1M borate buffer were added to afford dissolution of the glatiramer acetate in ultrasonic bath. The solution was further diluted with 0.1M borate buffer to obtain glatiramer stock solution 400 μg/ml (as base).

Workup

  1. customto afford

Sources & evidence

ORD record
ord-cd0efb693dc24e2f9644063a5636dd9f
Source dataset
uspto-grants-2013_02
Patent number
US08377885B2

Reaction notes

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