N'-Cbz-L-ornithine Chemical Properties

Melting point:

248-252℃

Boiling point:

492.2±45.0 °C(Predicted)

Density 

1.234±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

Acidic Alcohol (Sparingly), Aqueous Acid (Slightly)

pka

2.51±0.24(Predicted)

form 

Solid

color 

White

CAS DataBase Reference

3304-51-6(CAS DataBase Reference)

Safety Information

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

N'-Cbz-L-ornithine Usage And Synthesis

Chemical Properties

White powder

Uses

L-Orn(Z)-OH is used as a reactant in the synthesis of cyclic aminohexapeptides which showed antifungal activity.

Synthesis

The general procedure for the synthesis of (S)-2-amino-5-(((benzyloxy)carbonyl)amino)pentanoic acid from L-ornithine hydrochloride and benzyl chloroformate was as follows: 7.5 g of L-ornithine hydrochloride was dissolved in 89 mL of 0.5 mol/L sodium hydroxide solution, 5.55 g of anhydrous copper sulfate was added, and the reaction was carried out for 15 minutes. Subsequently, 6.15 g of anhydrous potassium carbonate and 8.2 mL of benzyl chloroformate were added and the reaction mixture was stirred at room temperature overnight. After completion of the reaction, the filtrate was washed to give a blue solid. The solid was treated with saturated disodium ethylenediaminetetraacetic acid solution, which was first heated to reflux for 2 hours and then left at room temperature overnight. Finally, the filtrate was filtered and dried to give a white solid product in 83% yield.

References

[1] Patent: CN104788431, 2017, B. Location in patent: Paragraph 0055; 0056
[2] Journal of Labelled Compounds and Radiopharmaceuticals, 2009, vol. 52, # 2, p. 29 - 32
[3] Tetrahedron, 1999, vol. 55, # 33, p. 10201 - 10220
[4] Journal of the Chemical Society [Section] C: Organic, 1971, p. 3743 - 3748
[5] Journal of Agricultural and Food Chemistry, 1999, vol. 47, # 3, p. 939 - 944

N'-Cbz-L-ornithine(3304-51-6)Related Product Information

• L-Ornithine
• Trimethoprim
• N-Carbobenzyloxyglycine
• N-δ-Boc-L-Ornithine
• H-Orn(2-Cl-Z)-OH
• N-Cbz-L-Leucine
• N-Cbz-L-histidine
• N-Cbz-L-Phenylalanine
• N-CBZ-L-glutamyl-L-tyrosine USP/EP/BP
• N-Cbz-L-Isoleucine
• H-Orn(Boc)-OBzl·HCl
• H-ORN(FMOC)-OH
• H-Orn(Tfa)-OH
• H-Orn(Trt)-OH
• H-Orn(Boc)-OtBu.HCl
• N(delta)-acetylornithine
• Ethyl L-ornithine dihydrochloride
• H-ORN(BOC)-OME HCL