Dimethylformamide → Benzyloxycarbonyl-L-phenylalanine

HRID 1646836Notes

Reaction equation

HRID 1646836 reaction equation
[CH3:1][O:2][C:3]([C:5](=[N:18][OH:19])[CH2:6][CH2:7][CH2:8][C@H:9]1[C@@H:17]2[C@@H:12]([NH:13][C:14]([NH:16]2)=[O:15])[CH2:11][S:10]1)=[O:4].[C:20]([NH:30][C@H:31]([C:39]([OH:41])=[O:40])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21].CN(C=O)C>O>[C:20]([NH:30][C@H:31]([C:39]([OH:41])=[O:40])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21].[CH3:1][O:2][C:3]([C:5](=[N:18][OH:19])[CH2:6][CH2:7][CH2:8][C@H:9]1[C@@H:17]2[C@@H:12]([NH:13][C:14]([NH:16]2)=[O:15])[CH2:11][S:10]1)=[O:4]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 131717718HCID 131717718, compound

Product 2

HCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 131717717HCID 131717717, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of N-CBZ-phenylalanine oximinobiotin methyl ester (10.0 mg, 0.018 mmol) in distilled H2O (0.99 mL)/DMF (0.01 mL) was treated with lipase (candida cylindracea, 3 mg, ca. 2000 units) and analyzed by HPLC. After 1 H, the probiotin was cleaved to form N-CBZ-phenylalanine and oximinobiotin methyl ester. Control samples containing no lipase did not show evidence of cleavage. The crude reaction mixture caused a displacement of HABA from the HABA/avidin or HABA/streptavidin complexes, confirming that the oximinobiotin methyl ester was produced by the hydrolysis. Control reactions which did not contain lipase failed to displace the HABA from the HABA/avidin or HABA/streptavidin complexes. This shows that probiotin did not bind to avidin or streptavidin until activated, that is until it was converted to oximinobiotin methyl ester, by lipase.

Sources & evidence

ORD record
ord-9330c4b1201d4ce2ae062fd2b354ca38
Source dataset
uspto-grants-1993_01
Patent number
US05182203

Reaction notes

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