L-Glutamine → Glycine methyl ester

HRID 1182018Notes

Reaction equation

HRID 1182018 reaction equation
[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6].B([O-])([O-])[O-].C([N:26]([CH2:31][C:32]([OH:34])=[O:33])CC(O)=O)C[N:17](CC(O)=O)[CH2:18][C:19](O)=[O:20]>>[NH2:17][CH2:18][C:19]([NH:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6])=[O:20].[CH3:2][O:34][C:32](=[O:33])[CH2:31][NH2:26]

Participants

5

Reactant 3

HCID 5961L-GlutamineHCID 6049Ethylenediaminetetraacetic AcidHCID 26574Borate

Product 2

HCID 69221Glycine methyl esterHCID 123913Glycylglutamine

Procedure

The synthesis reaction was carried out by incubating a reaction liquid containing 100 mM test amino acid methyl ester, 150 mM L-glutamine, 100 mM borate buffer (pH 9.0), 10 mM EDTA and enzyme (0.05 U/ml) for 3 hours at 25° C., followed by determination of the quantity of the produced peptides by HPLC. As a result, 52.19 mM glycyl-L-glutamine was produced in the case of using glycine methyl ester as the L-amino acid methyl ester, 5.94 mM L-valyl-L-glutamine was produced in the case of using L-valine methyl ester, 0.59 mM L-isoleucyl-L-glutamine was produced in the case of using L-isoleucyl-L-glutamine, 4.31 mM L-methionyl-L-glutamine was produced in the case of using L-methionine methyl ester, 3.67 mM L-phenylalanyl-L-glutamine was produced in the case of using L-phenylalanine methyl ester, 40.44 mM L-seryl-L-glutamine was produced in the case of using L-serine methyl ester, 3.85 mM L-threonyl-L-glutamine was produced in the case of using L-threonine methyl ester, 0.23 mM L-glutaminyl-L-glutamine was produced in the case of using L-glutamine methyl ester, 1.24 mM L-tyrosyl-L-glutamine was produced in the case of using L-tyrosine methyl ester, 6.52 mM L-arginyl-L-glutamine was produced in the case of using L-arginine methyl ester, and 8.22 mM L-aspartyl-α-L-glutamine was produced in the case of using L-aspartic acid-α-methyl ester. In addition, peptides composed of the corresponding amino acids and L-glutamines were also confirmed to be produced in the case of using L-leucine methyl ester, L-asparagine methyl ester, L-lysine methyl ester, L-aspartic acid-β-methyl ester, L-aspartic acid-α,β-dimethyl ester or L-glutamic acid-γ-methyl ester as the amino acid methyl ester (determination of quantity of these was not performed since no standard preparation was available).

Workup

  1. customThe synthesis reaction
  2. customa reaction liquid
  3. additioncontaining 100 mM
  4. customfor 3 hours
  5. customat 25° C.

Sources & evidence

ORD record
ord-c6a94f239a694866821baa367a31718a
Source dataset
uspto-grants-2007_10
Patent number
US07288388B2

Reaction notes

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