Pyruvic Acid → N-(1-Carboxyethyl)-L-alanyl-L-proline

HRID 2418405Notes

Reaction equation

HRID 2418405 reaction equation
[NH2:1][C@H:2]([C:4]([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5])[CH3:3].[C:14]([OH:19])(=[O:18])[C:15]([CH3:17])=O.C([BH3-])#N.[Na+]>O>[C:14]([CH:15]([NH:1][C@H:2]([C:4]([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5])[CH3:3])[CH3:17])([OH:19])=[O:18]

Participants

5

Reactant 3

HCID 1060Pyruvic AcidHCID 83525L-Alanyl-L-prolineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 53882949N-(1-Carboxyethyl)-L-alanyl-L-prolineYield 91.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of L-alanyl-L-proline (372 mg) and pyruvic acid (881 mg) in water is adjusted to pH 7 and treated with 377 mg of sodium cyanoborohydride at room temperature until reaction is complete. The product is absorbed on strong acid ion-exchange resin and then eluted with 2% pyridine in water. Freeze drying gives 472 mg of N-(1-carboxyethyl)-L-alanyl-L-proline. Nmr and mass spectrogram are consistent with structure. The nmr spectrum shows multiplets centered at 4.5, 3.7, and 2.2 ppm, and a pair of doublets at 1.6 ppm.

Workup

  1. customThe product is absorbed on strong acid ion-exchange resin
  2. washeluted with 2% pyridine in water
  3. customFreeze drying

Sources & evidence

ORD record
ord-9e685a2fc2f34c25972bfa4eafb40e51
Source dataset
uspto-grants-1984_09
Patent number
US04472380

Reaction notes

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