Fmoc-Orn(Boc)-OH Chemical Properties

Melting point:

111-115℃

Boiling point:

679.0±55.0 °C(Predicted)

Density 

1.226±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

soluble in Methanol

form 

powder to crystal

pka

3.85±0.21(Predicted)

color 

White to Almost white

BRN 

4772025

InChIKey

JOOIZTMAHNLNHE-NRFANRHFSA-N

SMILES

C(O)(=O)[C@H](CCCNC(OC(C)(C)C)=O)NC(OCC1C2=C(C=CC=C2)C2=C1C=CC=C2)=O

CAS DataBase Reference

109425-55-0(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29242990

MSDS

• Language:English Provider:SigmaAldrich

Fmoc-Orn(Boc)-OH Usage And Synthesis

Description

Fmoc-Orn(Boc)-OH is an ornithine-containing amino acid building block. It has been used to conjugate ornithine to GFP-labeled peptides, enhancing cell permeability when compared to unconjugated GFP-labeled peptides. This compound is useful in preparing cyclic peptides and special arginine derivates.

Chemical Properties

White powder

Uses

Fmoc-Orn(Boc)-OH is a biochemical reagent. It can be used as a biomaterial or organic compound in life science-related research.

Preparation

2 mmol L-Orn was weighted and dissolved in 15 ml of acetonitrile; 16 mmol Boc2O was dissolved in acetonitrile and added dropwise to an acetonitrile solution of ornithine, to react and generate a complex; 10 ml 20% sodium bicarbonate aqueous solution was added, and 2 g of anhydrous sodium carbonate and an appropriate amount of 8-hydroxyquinoline were added in batches; the mixture was stirred and reacted at room temperature for 4 hours to remove copper ions in the complex; then 2 mmol Fmoc-OSu was added to the aforesaid solution, followed by stirring at room temperature for 2 hours; the resultant was recrystallized with an ethyl acetate/petroleum ether mixed solvent, to obtain a peptide head intermediate Fmoc-Orn(Boc)-OH.

reaction suitability

Reaction type: Fmoc solid-phase peptide synthesis

Solubility in organics

DMF: 20 mg/ml, DMF:PBS (pH 7.2) (1:5): 0.16 mg/ml, DMSO: 10 mg/ml, Ethanol: 10 mg/ml

Fmoc-Orn(Boc)-OH(109425-55-0)Related Product Information

• Nalpha-Fmoc-Ndelta-trityl-L-glutamine
• Fmoc-Lys(Boc)-OH
• N-(tert-Butoxycarbonyl)-L-alanine
• 9-Fluorenylmethyl chloroformate
• Fmoc-O-trityl-L-serine
• Boc-Aib-OH
• L-Fmoc-Aspartic acid alpha-tert-butyl ester
• N-(9-Fluorenylmethoxycarbonyloxy)succinimide
• L(+)-Ornithine hydrochloride
• L-Ornithine
• Fmoc-Asp(OtBu)-OH
• Fmoc-Phe-OH
• N-Boc-N'-nitro-L-arginine
• 1,1'-Carbonyldiimidazole
• Fmoc-OrnMe(Alloc)-OH
• FMOC-ORN(ALOC)-OH
• FMOC-ORN(BOC)-OPFP
• Fmoc