FMOC-NLE-OH Chemical Properties

Melting point:

141-144 °C(lit.)

alpha 

-18.5 º (C=1 IN DMF)

Boiling point:

565.6±33.0 °C(Predicted)

Density 

1.209±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

pka

3.91±0.21(Predicted)

form 

Crystalline Powder

color 

White to off-white

optical activity

[α]20/D 18±1°, c = 1% in DMF

BRN 

5305164

CAS DataBase Reference

77284-32-3(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

2924 29 70

HazardClass 

IRRITANT

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

FMOC-NLE-OH Usage And Synthesis

Chemical Properties

White crystalline

Uses

Fmoc-Nle-OH, is an amino acid derivative used in chemical synthesis and peptide chemistry.

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

Synthesis

V-Fmoc allylglycine (100 mg, 0.296 mmol), degassed dichloromethane (6.0 mL), terminal olefins (1.48 mmol, 5 eq.), and HGII catalyst (9.29 mg, 5 mol%) were added to a Schlenk reaction flask equipped with a magnetic stirring bar in a drying oven under nitrogen atmosphere. After sealing the reaction flask, it was removed from the desiccator and connected to a vacuum system. The reaction vial was placed under a stream of nitrogen and the quick assembly stopper was replaced with a sub-seal with a 26-gauge pinhole to ensure a continuous flow of nitrogen across the top of the reaction system. The reaction mixture was stirred overnight at room temperature, followed by evaporation of all dichloromethane. The residue was washed with hexane (2 x 10 mL) and collected by filtration or centrifugation. The resulting residue was redissolved in methanol (10 mL) and transferred to a Fischer-Porter reaction tube. The reaction tube was filled with hydrogen (60 psi), sealed and stirred overnight at room temperature. Upon completion of the reaction, the mixture was concentrated under vacuum and the residual brown solid was purified by column chromatography to give the pure Fmoc amino acid analog. Alternatively, the residual brown solid is dissolved in a small amount of ether, the insoluble material is removed by filtration, and the filtrate is concentrated under vacuum to give an off-white solid.

References

[1] Journal of Peptide Science, 2013, vol. 19, # 8, p. 470 - 476
[2] Patent: WO2014/5197, 2014, A1. Location in patent: Page/Page column 48-49

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