L-Valine → L-Alanine

HRID 1382180Notes

Reaction equation

HRID 1382180 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 0.6M Valine-0.1M KCl-1 mM EDTA, pH 9.8 was mixed with 100 μl (0.1 mmole) of a 1M 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 0.5M 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 6M 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 6M 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-42a9b3357a2b4e55a852306386a0160b
Source dataset
uspto-grants-1989_02
Patent number
US04806473

Reaction notes

Loading…