Ubenimex → L-Leucine

HRID 972250

Reaction equation

HRID 972250 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

HCID 72172Ubenimex

Product 1

HCID 6106L-Leucine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The hydrolysis of bestatin in 6N 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-d933097c8a2a46e685fa1b46a76d973b
Source dataset
uspto-grants-1977_10
Patent number
US04052449

Linked notes

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