| Identification | More | [Name]
FMOC-L-Leucine | [CAS]
35661-60-0 | [Synonyms]
2-[[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]AMINO]-4-METHYLPENTANOIC ACID
9-FLUORENYLMETHOXYCARBONYL-L-LEUCINE
F-L-LEU
FMOC-LEU
FMOC-LEUCINE
FMOC-LEU-OH
FMOC-L-LEU
FMOC-L-LEUCINE
FMOC-L-LEU-OH
N-(9-FLUORENYLMETHOXYCARBONYL)-L-LEUCINE
N-9-FLUORENYLMETHYLOXYCARBONYL-L-LEUCINE
N-[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]-L-LEUCINE
N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-L-LEUCINE
N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-L-LEUCINE
N-ALPHA-FMOC-L-LEUCINE
N-FMOC-LEU-OH
N-FMOC-L-LEU
N-FMOC-L-LEUCINE
NPC 15199
PPAR-GAMMA ACTIVATOR | [EINECS(EC#)]
252-662-7 | [Molecular Formula]
C21H23NO4 | [MDL Number]
MFCD00037133 | [Molecular Weight]
353.41 | [MOL File]
35661-60-0.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powde | [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. ]
2-8°C
| [solubility ]
DMF (Slightly), DMSO (Slightly) | [form ]
Solid | [pka]
3.91±0.21(Predicted) | [color ]
White to Off-White | [Optical Rotation]
[α]20/D 25±2°, c = 1% in DMF | [Detection Methods]
T,NMR,HPLC,Rotation | [BRN ]
2178254 | [Stability:]
Hygroscopic | [Major Application]
peptide synthesis | [InChI]
1S/C21H23NO4/c1-13(2)11-19(20(23)24)22-21(25)26-12-18-16-9-5-3-7-14(16)15-8-4-6-10-17(15)18/h3-10,13,18-19H,11-12H2,1-2H3,(H,22,25)(H,23,24)/t19-/m0/s1 | [InChIKey]
CBPJQFCAFFNICX-IBGZPJMESA-N | [SMILES]
CC(C)C[C@H](NC(=O)OCC1c2ccccc2-c3ccccc13)C(O)=O | [CAS DataBase Reference]
35661-60-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302-H315-H319-H335 | [Precautionary statements ]
P261-P280-P301+P312-P302+P352-P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S27:Take off immediately all contaminated clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [REACH Registrations]
Active | [HS Code ]
29242990 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [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 | [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. | [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. | [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. | [Biochem/physiol Actions]
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 |
|
| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
Alfa Aesar
|
| Telephone: |
400-6106006 |
| Website: |
http://chemicals.thermofisher.cn |
|