FMOC-D-Valine Chemical Properties

Melting point:

143-144 °C(lit.)

alpha 

17 º (c=1, DMF)

Boiling point:

551.8±33.0 °C(Predicted)

Density 

1.229±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), DMF (Slightly), DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

3.90±0.10(Predicted)

color 

White

optical activity

Consistent with structure

Water Solubility 

Solubility in methanol (almost transparency). Slightly soluble in water.

BRN 

6489548

CAS DataBase Reference

84624-17-9(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

2924 29 70

MSDS

• Language:English Provider:SigmaAldrich

FMOC-D-Valine Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

N-Fmoc-D-valine is an N-Fmoc-protected form of D-Valine (V094200). D-Valine (an isomer of the essential amino acid L-Valine [V094205])exhibited inhibitory effects on fibroblasts that contaminated mammalian kidney cultures, allowing for selective growth epithelial cells. D-Valine is also known for its presence in the structure of Actinomycin D, an antitumour drug. D-Valine is naturally synthesized by Streptomyces antibioticus.

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

Synthesis

General procedure for the synthesis of Fmoc-D-valine from D-valine and chloroformic acid-9-fluorenylmethyl ester: A 500 mL three-necked flask was taken, and D-valine (4.5 g, 38.9 mmol), dioxane (40 mL), and 10% aqueous sodium carbonate (100 mL) were added sequentially. The reaction system was placed in an ice bath and mechanical stirring was initiated. A dioxane solution (100 mL) of methyl chloroformate-9-fluorenyl (10.0 g, 38.8 mmol) was prepared in a dropping funnel and slowly added dropwise to the reaction vial. After the dropwise addition was completed, it was gradually brought to room temperature and stirring was continued overnight. After completion of the reaction, 100 mL of water was added to the reaction mixture and extracted three times with 50 mL of ether and the organic phase was discarded. The aqueous phase was cooled in an ice bath, and the pH was adjusted to 1 by slowly adding 1 M dilute hydrochloric acid, followed by extracting the aqueous phase with 50 mL ethyl acetate three times, combining the organic phases and drying with anhydrous magnesium sulfate. The desiccant was removed by filtration and the organic phase was concentrated under reduced pressure to give the white solid product Fmoc-D-valine (12.6 g, 96% yield).

References

[1] Patent: CN106588987, 2017, A. Location in patent: Paragraph 0172; 0173; 0174
[2] Chemistry - A European Journal, 2014, vol. 20, # 21, p. 6526 - 6531

FMOC-D-Valine(84624-17-9)Related Product Information

• L-Valine
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• Fmoc-D-Ile-OH
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• NICKEL CARBONYL