L-Leucine → L-Tyrosine

HRID 495333

Reaction equation

HRID 495333 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].C(O[C:13](=[O:20])[C@H:14](CC(C)C)N)C.[NH2:21][C@H:22]([C:27]([OH:29])=[O:28])[CH2:23][CH2:24][S:25][CH3:26]>>[NH2:21][C@H:22]([C:27]([OH:29])=[O:28])[CH2:23][CH2:24][S:25][CH3:26].[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4]1[CH:6]=[CH:14][C:13]([OH:20])=[CH:22][CH:5]=1

Participants

5

Reactant 3

HCID 6106L-Leucine2×HCID 6137L-MethionineHCID 75971L-Leucine ethyl ester

Product 2

HCID 6057L-TyrosineHCID 6137L-Methionine

Procedure

The papain-catalyzed synthesis of leucine and HMB co-oligomers was performed. Synthesis of leucine oligomers and HMB-leucine co-oligomers was initiated with leucine ethyl ester and HMB ethyl ester as the substrates. The overall synthesis and purification approach was similar to the one used in the case of methionine and HMB-methionine. Reaction rates similar to those obtained with methionine and tyrosine were achieved. Approximate oligomer yield was 58%. The freeze-dried oligomer precipitates were solubilized in DMSO. The solution concentration was brought to approximately 2 μg/μl The solution was mixed with 1:1 acetonitrile:water mixture containing 0.1% acetic acid. The total fluid volume entering the ESI-MS was maintained at 0.2 mL min.−1 The positive mass spectrum of the leucine oligomers is shown in FIG. 33A.

Workup

  1. customThe overall synthesis and purification approach
  2. customReaction rates similar to

Sources & evidence

ORD record
ord-dc7beefece054ece995580c4f7aab15d
Source dataset
uspto-grants-2005_09
Patent number
US06939693B2

Linked notes

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