N-Benzyloxycarbonyl-L-proline Chemical Properties

Melting point:

75-77 °C

alpha 

-60 º (c=2,AcOH)

Boiling point:

392.36°C (rough estimate)

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

InChI

InChI=1S/C13H15NO4/c15-12(16)11-7-4-8-14(11)13(17)18-9-10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2,(H,15,16)/t11-/m0/s1

InChIKey

JXGVXCZADZNAMJ-NSHDSACASA-N

SMILES

N1(C(OCC2=CC=CC=C2)=O)CCC[C@H]1C(O)=O

CAS DataBase Reference

1148-11-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

62-36/37/38-20/21/22

Safety Statements 

22-24/25-36-26

WGK Germany 

3

RTECS 

UY0745000

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:Z-Pro-OH
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

N-Benzyloxycarbonyl-L-proline Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

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.

reaction suitability

reaction type: solution phase peptide synthesis

N-Benzyloxycarbonyl-L-proline(1148-11-4)Related Product Information

• L-PROLINE-(4-3H(N))
• Trimethoprim
• cis-4-Hydroxy-L-proline
• L-Proline
• D-Proline
• N-Carbobenzyloxyglycine
• Z-PRO-GLY-OH
• N-Cbz-L-Serine
• Z-PRO-PHE-OH
• N-alpha-Benzyloxycarbonyl-L-proline amide
• N-Cbz-L-Tryptophan
• N-Cbz-L-Threonine
• N-Cbz-L-Phenylalanine
• N-Cbz-L-glutamic acid
• Z-PRO-GLY-NH2
• Z-PRO-BETANA
• Z-PRO-PRO-OH
• Z-PRO-ONP