4-Methyl-L-glutamate → gamma-methyl-L-glutamic acid gamma-hexyl-L-glutamic acid
Reaction equation
[CH3:1][CH:2]([C:9]([OH:11])=[O:10])[CH2:3][C@@H:4]([C:6]([OH:8])=[O:7])[NH2:5].[CH2:12]([CH:18]([C:25]([OH:27])=[O:26])[CH2:19][C@@H:20]([C:22]([OH:24])=[O:23])[NH2:21])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>>[CH3:1][CH:2]([C:9]([OH:11])=[O:10])[CH2:3][C@@H:4]([C:6]([OH:8])=[O:7])[NH2:5].[CH2:12]([CH:18]([C:25]([OH:27])=[O:26])[CH2:19][C@@H:20]([C:22]([OH:24])=[O:23])[NH2:21])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]Participants
3
Procedure
The synthesized copolymer (10 mg) was dissolved in deuterated trifluoroacetic acid, and the 1H NMR was measured. As a result, a peak derived from the methyl group of γ-methyl-L-glutamic acid was detected near 3.8 ppm, and a peak derived from the proton at the α-position of γ-methyl-L-glutamic acid and γ-hexyl-L-glutamic acid was detected near 4.7 ppm. When peak area near 3.8 ppm is A and that near 4.7 ppm is B, A/B=1.17. Since A/B=3.00 for poly-γ-methyl-L-glutamic acid, the decreased portion is considered to be substituted by a hexyl group. Therefore, the content percentage of the hexyl group is 61% since 1.83/3.00=0.61. Hence, the composition of the copolymer is γ-methyl-L-glutamic acid (39%)/γ-hexyl-L-glutamic acid (61%).
Sources & evidence
- ORD record
- ord-2421fb0b2bf94f1195d8862a868d39a2
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09450174B2
Reaction notes
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