Fmoc-Leu-OH Chemical Properties

Melting point:

152-156 °C(lit.)

alpha 

-26 º (c=1,DMF 24 ºC)

Boiling point:

486.83°C (rough estimate)

Density 

1.2107 (rough estimate)

refractive index 

-25 ° (C=1, DMF)

storage temp. 

Store below +30°C.

solubility 

DMF (Slightly), DMSO (Slightly)

form 

Solid

pka

3.91±0.21(Predicted)

color 

White to Off-White

optical activity

[α]20/D 25±2°, c = 1% in DMF

BRN 

2178254

Stability:

Hygroscopic

InChIKey

CBPJQFCAFFNICX-IBGZPJMESA-N

CAS DataBase Reference

35661-60-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-36/37/39-27-26

WGK Germany 

3

HS Code 

2924 29 70

MSDS

• Language:English Provider:N-(9-Fluorenylmethoxycarbonyl)-L-leucine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Fmoc-Leu-OH Usage And Synthesis

Description

Fmoc-Leu-OH is isomeric with Fmoc-Ile-OH. Like isoleucine, leucine has branching in the sidechain. The branching is at the gamma carbon instead of the beta carbon as in isoleucine. It is used in chemical and peptide syntheses.

Chemical Properties

white to light yellow crystal powde

Uses

Fmoc-L-Leu-OH, is an amino acid derivative, used in peptide chemistry. It is also one of the novel PPARγ ligands that can activate PPARγ in different ways, that reduces osteoclasts differentiation, and thus are better therapeutic targets in diabetes than traditional antidiabetic drugs.

Application

Fmoc-Leu-OH can be used as a reactant to synthesize:
Various oligopeptides by reacting with functionalized α-amino acid hydrochloride salts.
A cyclic depsipeptide sansalvamide A, a natural product found in marine fungus.
Streptocidin A?D, decapeptide antibiotics naturally found in Streptomyces?sp. Tü 6071.
Coumaroyl dipeptide amide that can be used for cosmetic applications.

Preparation

Fmoc-L-leucine is prepared by reacting L-leucine with 9-fluorenylmethoxycarbonyl chloride.

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

Biological Activity

Anti-inflammatory agent; increases intracellular Ca 2+ levels. PPARγ ligand that induces insulin sensitization, but not adipogenesis.

Synthesis

The general procedure for the synthesis of Fmoc-L-leucine and compound (CAS:139551-97-6) using compound (CAS:103321-59-1) as starting material was as follows:Example 22 Synthesis of N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-leucine amide (NPC 15528). To a 10 mL THF solution containing 3.5 mL (10 mmol) of N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-leucine chloride, 1.26 mL (20 mmol) of a 29.6% ammonia solution was slowly added at room temperature. The reaction mixture was stirred for 30 min, then diluted with 100 mL of water and extracted with ethyl acetate (5 x 20 mL). The organic layers were combined and washed sequentially with 10% potassium carbonate solution, water and brine, then dried and concentrated. The product was recrystallized by ethanol to give 1.26 g (36% yield) of N-(9-fluorenylmethoxycarbonyl)-L-leucine amide as a colorless solid with a melting point of 79-80 °C.

References

[1] Patent: US5079260, 1992, A

Fmoc-Leu-OH(35661-60-0)Related Product Information

• L-Leucine
• N-CARBOBENZOXY-DL-LEUCINE
• L-tert-Leucine
• Glycine
• Fmoc-Aib-OH
• 9-Fluorenylmethyl chloroformate
• FMOC-Ala-OH
• Fmoc-Lys(Boc)-OH
• FMOC-N-METHYL-TRANEXAMIC ACID
• Fmoc-L-Tyr(propargyl)-OH
• Fmoc-Gly-OH
• FMOC-O-tert-Butyl-L-serine
• Fmoc-Asn(Trt)-OH
• FMOC-TRANEXAMIC ACID
• Nalpha-Fmoc-Ndelta-trityl-L-glutamine
• Fmoc-Tyr(tBu)-OH
• Fmoc-OSu
• FMOC-METRP-OH