L-Tyrosine ethyl ester → HCID 12136556, compound

HRID 1464236Notes

Reaction equation

HRID 1464236 reaction equation
[NH2:1][C@H:2]([C:11]([O:13]CC)=O)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[NH2:16][C@H:17]([C:22]([O:24]CC)=[O:23])[CH2:18][CH2:19][CH2:20][NH2:21].Cl.Cl>>[NH2:1][C@H:2]([C:11]([NH:16][C@H:17]([C:22]([OH:24])=[O:23])[CH2:18][CH2:19][CH2:20][NH2:21])=[O:13])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 70364L-Tyrosine ethyl esterHCID 44151258Ethyl L-ornithine dihydrochloride

Product 1

HCID 12136556HCID 12136556, compound

Procedure

It is also possible according to the present invention to employ a non-proteinogenic amino acid as a nucleophile. Mal-Tyr-OEt, an electrophile, and Orn-OEt.2HCl, a nucleophile, were reacted using α-CT as a catalyst. After a reaction time of 20 minutes, the solution was concentrated, the enzyme was separated off by ultrafiltration with a membrane with MWCO 10,000, and the dissolved fraction was lyophilized. Both Mal-Tyr-Orn and the Orn delta-lactam cyclization product were isolated by preparative HPLC and identified by 1H-NMR. The combined yield of the two products (about 1:1) was about 45-50%.

Workup

  1. concentrationAfter a reaction time of 20 minutes, the solution was concentrated
  2. customthe enzyme was separated off by ultrafiltration with a membrane with MWCO 10,000

Sources & evidence

ORD record
ord-0bca59d7e6cf4e388a35835e90f152f0
Source dataset
uspto-grants-1994_04
Patent number
US05304470

Reaction notes

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