Ubenimex → L-Leucine
Reaction equation
[CH3:1][CH:2]([CH2:4][C@H:5]([NH:9]C([C@@H](O)[C@H](N)CC1C=CC=CC=1)=O)[C:6]([OH:8])=[O:7])[CH3:3]>Cl>[NH2:9][C@H:5]([C:6]([OH:8])=[O:7])[CH2:4][CH:2]([CH3:3])[CH3:1]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
The hydrolysis of bestatin in 6 N HCl at 100° C. for 18 hours yields L-leucine and an unusual amino acid. The ratio of these amino acids is 1:1. Bestatin gives positive Rydon-Smith and ninhydrin reactions. The amino acid sequence of bestatin shown in the structure was elucidated by fragmentation pattern in mass spectrum of bestatin methyl ester hydrochloride. Thus, the structure of bestatin is (2S,3R)-3-amino-2-hydroxy-4-phenylbutyryl-L-leucine.
Sources & evidence
- ORD record
- ord-40fb644ac47b47518b3d1cc593b69f10
- Source dataset
- uspto-grants-1979_12
- Patent number
- US04179573
Reaction notes
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