L-Leucinamide hydrochloride

L-Leucinamide hydrochloride Property

Melting point:

254256°C

alpha 

9 º (c=1, H2O)

refractive index 

9.8 ° (C=5, H2O)

storage temp. 

Inert atmosphere,Room Temperature

Water Solubility 

very faint turbidity in Water

form 

Powder

color 

White to off-white

optical activity

[α]25/D +10°, c = 5 in H2O

Sensitive 

Hygroscopic

BRN 

4237021

CAS DataBase Reference

10466-61-2(CAS DataBase Reference)

Safety

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

29241900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H225Highly Flammable liquid and vapour

H317May cause an allergic skin reaction

H318Causes serious eye damage

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.

P403+P235Store in a well-ventilated place. Keep cool.

L-Leucinamide hydrochloride Chemical Properties,Usage,Production

Chemical Properties

Crystalline

Uses

L-Leucinamide Hydrochloride, is a derivative of Leucine, which is an essential amino acid, and acts as a nutrient signal to stimulate protein synthesis. L-Leucinamide Hydrochloride, is shown to be the potential elicitors of insulin secretion in rats.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

The general procedure for the synthesis of L-leucinamide hydrochloride from L-leucine methyl ester hydrochloride is as follows: the synthesis is an improvement on a previously published method. The raw material L-leucine methyl ester hydrochloride can be purchased from Alfa Aesar. L-Leucine methyl ester hydrochloride (1.0 g, 5.5 mmol) and methanol (10 mL) were added to a glass pressure tube, followed by a methanol solution of 7N ammonia (7.9 mL, 55 mmol). The reaction tube was sealed, heated to 50 °C and kept for 2 days. After completion of the reaction, the mixture was concentrated in vacuum. The crude product was suspended in 1,4-dioxane (10 mL) and converted to hydrochloride by addition of 1,4-dioxane solution (1.7 mL, 6.8 mmol) in 4N HCl. Mixing was facilitated by sonication. The solvent and excess HCl were removed using a rotary evaporator, 1,4-dioxane (10 mL) was added during the process to help remove excess HCl.The product was purified by recrystallization from hot isopropanol, allowing crystals to form slowly at room temperature. The recrystallized solid was placed under high vacuum to remove residual solvent. The final yield was 0.55 g (60%). The product had a melting point of 216-218 °C, a specific spin [α]D24 of +12.0° (c 0.50, methanol), and an HPLC purity (200 nm) greater than 99% and significantly lower than 0.5% of the parent leucine.1H NMR ((CD3)2SO) δ 8.29 (broad single peak, 3H), 7.96 (single peak, 1H), 7.48 (single peak, 1H), and 3.66 (multiple peaks, 1H), 1.67 (multiple peaks, 1H), 1.56 (multiple peaks, 2H), 0.92 (double peaks, J=3Hz, 3H), 0.90 (double peaks, J=3Hz, 3H).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 20, p. 5000 - 5006
[2] Journal fur Praktische Chemie - Chemiker - Zeitung, 1996, vol. 338, # 3, p. 251 - 256