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HomeProduct name listN-Benzyloxycarbonyl-L-proline

N-Benzyloxycarbonyl-L-proline

Synonym(s):Z-L-Proline

  • CAS NO.:1148-11-4
  • Empirical Formula: C13H15NO4
  • Molecular Weight: 249.26
  • MDL number: MFCD00003170
  • EINECS: 214-557-4
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-10-31 21:04:56
N-Benzyloxycarbonyl-L-proline Structural

What is N-Benzyloxycarbonyl-L-proline?

Chemical properties

white to light yellow crystal powder

The Uses of N-Benzyloxycarbonyl-L-proline

N-(Benzyloxycarbonyl)-L-proline is a potent in vitro and in vivo inhibitor of prolidase; a specific peptidase that cleaves dipeptides with a C-terminal prolyl and hydroxylprolyl residue. It is also used in the synthesis of N-(L-Prolyl)-β-alanine which is a derivative of the naturally occurring beta amino acid β-Alanine.

Preparation

Caution! All procedures must be carried out in an efficient fume cupboard, wearing latex gloves and chemical-proof safety goggles. ι-Proline (10.0 g, 8.7 mmol) was dissolved in 2 m sodium hydroxide solution (40 mL), and the solution was cooled to ice-water temperature. Z-Cl (20.5 g, 12 mmol) was added portionwise, with vigorous stirring or occasional shaking, over a period of 30 min at 0–5 °C to the solution of l-proline. The ice bath was then removed and stirring or occasional shaking was continued for 30 min while the reaction mixture warmed to room temperature. The mixture was then acidified to Congo red by the gradual addition of concentrated hydrochloric acid, and the oil was extracted into ethyl acetate. The extract was dried over magnesium sulfate, the mixture was filtered, and the filtrate was concentrated in vacuo. The residue was extracted/triturated with warm tetrachloromethane. The washings were decanted and the residue was further purified by recrystallization from ethyl acetate/petroleum ether.

Effects

Results demonstrated that N-benzyloxycarbonyl-l-proline (Cbz-Pro) is a potent inhibitor of prolidase in cultured fibroblasts and it can be used in vivo to better characterize the prolidase enzyme and further investigate PD physiopathology.

Properties of N-Benzyloxycarbonyl-L-proline

Melting point: 75-77 °C
Boiling point: 392.36°C (rough estimate)
alpha  -60 º (c=2,AcOH)
Density  1.1952 (rough estimate)
refractive index  -40 ° (C=2, EtOH)
storage temp.  Sealed in dry,Room Temperature
solubility  Solubility in methanol, almost transparency.
form  Crystalline Powder or Crystals
pka 3.99±0.20(Predicted)
color  White to off-white
optical activity [α]20/D 42°, c = 2 in ethanol
BRN  88579
CAS DataBase Reference 1148-11-4(CAS DataBase Reference)

Safety information for N-Benzyloxycarbonyl-L-proline

Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.

Computed Descriptors for N-Benzyloxycarbonyl-L-proline

InChIKey JXGVXCZADZNAMJ-NSHDSACASA-N

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