epsilon-(Benzyloxycarbonyl)-L-lysine → gamma-benzyl-L-glutamic acid Nepsilon-benzyloxycarbonyl-L-lysine

HRID 64533Notes

Reaction equation

HRID 64533 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@@H:16]([C:18]([OH:20])=[O:19])[NH2:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]([CH:28]([C:35]([OH:37])=[O:36])[CH2:29][C@@H:30]([C:32]([OH:34])=[O:33])[NH2:31])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[CH2:21]([CH:28]([C:35]([OH:37])=[O:36])[CH2:29][C@@H:30]([C:32]([OH:34])=[O:33])[NH2:31])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1.[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@@H:16]([C:18]([OH:20])=[O:19])[NH2:17])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 1715626epsilon-(Benzyloxycarbonyl)-L-lysine3×HCID 22787902gamma-benzyl-L-glutamic acid3×

Product 1

HCID 86718960gamma-benzyl-L-glutamic acid Nepsilon-benzyloxycarbonyl-L-lysine

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 benzyl group of Nε-benzyloxycarbonyl-L-lysine and the benzyl group of γ-benzyl-L-glutamic acid was detected near 5.1 ppm, a peak derived from the proton at the α-position of γ-benzyl-L-glutamic acid was detected near 4.7 ppm, and a peak derived from the proton at the α-position of Nε-benzyloxycarbonyl-L-lysine was detected near 4.4 ppm. When the peak areas near 5.1 ppm, 4.7 ppm, 4.4 ppm are A, B, C, respectively, A/B=4.00, A/C=4.00, and B/C=1.00. Since both B and C represent an area of one proton, the composition of the copolymer is γ-benzyl-L-glutamic acid (50%)/Nε-benzyloxycarbonyl-L-lysine (50%).

Sources & evidence

ORD record
ord-d2361c97e90743c2bd9752cc01be3734
Source dataset
uspto-grants-2016_09
Patent number
US09450174B2

Reaction notes

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