Fmoc-L-leucine

Base Information

• Chemical Name: Fmoc-L-leucine
• CAS No.: 35661-60-0
• Molecular Formula: C21H23NO4
• Molecular Weight: 353.418
• Hs Code.: 2922.49
• European Community (EC) Number: 252-662-7
• UNII: KF18F70UF3
• DSSTox Substance ID: DTXSID0040751
• Nikkaji Number: J256.549H
• Wikidata: Q27282223
• ChEMBL ID: CHEMBL149394
• Mol file: 35661-60-0.mol

Synonyms:N-(fluorenyl-9-methoxycarbonyl)leucine;NPC 15199;NPC 15199, (D)-isomer;NPC-15199

Chemical Property of Fmoc-L-leucine

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 2.28E-13mmHg at 25°C
• Melting Point: 152-156 °C(lit.)
• Refractive Index: -25 ° (C=1, DMF)
• Boiling Point: 559.8 °C at 760 mmHg
• PKA: 3.91±0.21(Predicted)
• Flash Point: 292.4 °C
• PSA: 75.63000
• Density: 1.207 g/cm³
• LogP: 4.41530
• Storage Temp.: 2-8°C
• Solubility.: DMF (Slightly), DMSO (Slightly)
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 353.16270821
• Heavy Atom Count: 26
• Complexity: 484

Purity/Quality:

99%, ^*data from raw suppliers

NPC 15199 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36/37/39-27-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: CC(C)CC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: CC(C)C[C@@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• 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. 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.

Technology Process of Fmoc-L-leucine

There total 40 articles about Fmoc-L-leucine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

N-Fmoc-leucine benzyl ester → Fmoc-Leu-OH (35661-60-0)

Guidance literature:

With hydrogen; In ethanol; for 0.75h;

DOI:10.1039/c0ob00962h

Reference yield: 92.0%

(2S)-N-<(fluoren-9-yl)methoxycarbonyl>leucine prop-2-enyl ester (146549-16-8) → Fmoc-Leu-OH (35661-60-0)

Guidance literature:

With water; chlortris(triphenylphosphine)rhodium; In ethanol; for 2h;

DOI:10.1002/hlca.19920750812

Reference yield: 91.0%

L-leucine (61-90-5,21675-61-6,25248-98-0,70-45-1) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → Fmoc-Leu-OH (35661-60-0)

Guidance literature:

With sodium hydrogencarbonate; In acetone; Ambient temperature;

upstream raw materials:

L-leucine

(fluorenylmethoxy)carbonyl chloride

9-fluorenylmethyl N-succinimidyl carbonate

(9-fluorenyl)methyl pentafluorophenyl carbonate

Downstream raw materials:

H-Tyr-Gly-Gly-Phe-Leu-NH₂

Refernces

• 1、 -. "Kras inhibitory cyclic peptide compound". Paragraph 0682; 0821; 0824. . Retrieved 2021/06/03.
• 2、 Islam, Md. Fokhrul,Adhikari, Suraj,Paik, Man-Jeong,Lee, Wonjae. "Determination of Chemical and Enantiomeric Purity of α-Amino Acids and their Methyl Esters as N-Fluorenylmethoxycarbonyl Derivatives Using Amylose-derived Chiral Stationary Phases". . p. 332 - 338. Retrieved 2019/04/13.