L-Valine → L-Alanine

HRID 1759235Notes

Reaction equation

HRID 1759235 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3](C)C.N(C(C1C=CC=CC=1)=O)[C@H](C(OC)=O)C.[OH-].[Na+].N(C(C1C=CC=CC=1)=O)[C@H](C([NH:31][C@H:32]([C:36]([OH:38])=[O:37])[CH:33]([CH3:35])[CH3:34])=O)C>Cl>[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH3:3].[NH2:31][C@H:32]([C:36]([OH:38])=[O:37])[CH:33]([CH3:35])[CH3:34]

Participants

7

Reactant 4

HCID 6287L-ValineHCID 14798Sodium HydroxideHCID 63646177244-67-9HCID 54510848HCID 54510848, compound

Product 2

HCID 5950L-AlanineHCID 6287L-Valine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

A solution of 2 ml of 0.6 M Valine-0.1 M KCl-1 mM EDTA, pH 9.8 was mixed with 100 μl (0.1 mmole) of a 1 M Bz-Ala-OMe (dissolved in 96% ethanol) solution. The reaction was carried out in a pH-stat at 35° C. and pH 9.8, the pH-value being kept constant by automatic addition of 0.5 M NaOH. The reaction was initiated by adding 0.7 mg of carboxypeptidase Y (150 U/mg, prepared by De Forenede Bryggerier). After a reaction time of 30 minutes, the reaction was discontinued by adjusting pH to about pH=1 with 6 M HCl. The reaction product was purified and isolated by means of high pressure chromatography. The yield of Bz-Ala-Val-OH was 40%. Quantitative amino acid analysis after hydrolysis of the product in 6 M HCl for 24 hours gave relatively 1.0 mole of Alanine and 1.0 mole of Valine.

Workup

  1. customwas carried out in a pH-stat at 35° C.
  2. additionby adding
  3. custom0.7 mg of carboxypeptidase Y (150 U/mg, prepared by De Forenede Bryggerier)
  4. customAfter a reaction time of 30 minutes
  5. customThe reaction product was purified
  6. customisolated by means of high pressure chromatography

Sources & evidence

ORD record
ord-6df290a14e314d5ba3cb489998302b57
Source dataset
uspto-grants-1982_07
Patent number
US04339534

Reaction notes

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