DL-Phenylalanine, methyl ester → 33605-76-4

HRID 356570Notes

Reaction equation

HRID 356570 reaction equation
[CH:1]([NH:3][C@H:4]([C:9]([OH:11])=O)[CH2:5][C:6]([OH:8])=[O:7])=[O:2].[CH3:12][O:13][C:14](=[O:24])[C@H:15]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[NH2:16].COC(=O)C(CC1C=CC=CC=1)N>O>[CH3:12][O:13][C:14](=[O:24])[C@H:15]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[NH:16][C:9](=[O:11])[C@H:4]([CH2:5][C:6](=[O:7])[OH:8])[NH:3][CH:1]=[O:2]

Participants

5

Reactant 3

HCID 75737DL-Phenylalanine, methyl ester2×HCID 88052N-formyl-L-aspartic acid2×HCID 736234L-Phenylalanine, methyl ester

Product 1

HCID 1026805633605-76-4

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An enzymatic method for producing N-formyl-α-L-aspartyl-L-phenylalanine methyl ester by a condensation reaction between N-formyl-L-aspartic acid and L-phenylalanine methyl ester or D,L-phenylalanine methyl ester, which comprises: supplying an organic phase comprising a water-immiscible solvent containing N-formyl-L-aspartic acid and L- or D,L-phenylalanine methyl ester onto an aqueous phase comprising a thermolysin-like metalloprotease; proceeding the condensation reaction in the aqueous phase to produce N-formyl-α-L-aspartyl-L-phenylalanine methyl ester; and extracting the N-formyl-α-L-aspartyl-L-phenylalanine methyl ester thus produced from the aqueous phase to the organic phase.

Workup

  1. customthe condensation reaction in the aqueous phase

Sources & evidence

ORD record
ord-b3c63939a8904acf931c8a4fe8f3c568
Source dataset
uspto-grants-1998_11
Patent number
US05837483

Reaction notes

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