198544-60-4

Basic information

• Product Name: FMOC-D-LEU-CL
• Synonyms: FMOC-D-LEU-CL;FMOC-D-LEUCYL CHLORIDE;Fmoc-D-leucyl chloride99%
• CAS NO: 198544-60-4
• Molecular Formula: C₂₁H₂₂ClNO₃
• Molecular Weight: 371.86
• Product Categories: Amino Acids
• Mol File: 198544-60-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 518.8±33.0 °C(Predicted)
• Appearance: /
• Density: 1.213±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 10.36±0.46(Predicted)
• CAS DataBase Reference: FMOC-D-LEU-CL(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-D-LEU-CL(198544-60-4)
• EPA Substance Registry System: FMOC-D-LEU-CL(198544-60-4)

Safety Data

• Hazardous Substances Data: 198544-60-4(Hazardous Substances Data)

Usage

General Description

FMOC-D-LEU-CL, also known as 9-Fluorenylmethyl chloroformate-D-Leucine, is a chemical compound used in the synthesis of peptides and proteins. It is a derivative of leucine, an essential amino acid, and is commonly used as a reagent for protecting the amino group during peptide synthesis. FMOC-D-LEU-CL is a white to off-white crystalline powder that is soluble in organic solvents such as dimethylformamide and dichloromethane. It is primarily used in the field of biochemistry and pharmaceutical research for the production of synthetic peptides and small proteins. FMOC-D-LEU-CL is also utilized in the development of new drugs and pharmaceuticals.

Upstream product

• 35661-60-0 N-(9-fluorenylmethoxycarbonyl)-D-leucine 

Downstream Products

• 264282-01-1 N-(2-phenylethyl)-N-(hydroxy)-N_α-Fmoc-D-leucinamide 
• 264281-98-3 N-(2-phenylethyl)-N-(benzoyloxy)-N_α-Fmoc-D-leucinamide 

Relevant articles and documents

Synthesis of N-(hydroxy)amide- and N-(hydroxy)thioamide-containing peptides

Methods developed with N-(benzoyloxy)amines and hydroxamic acids were used in the synthesis of N-(hydroxy)amide-containing pseudopeptides. Acylation of N-(benzoyloxy)phenethylamine with the acid chloride of N(α)- Fmoc-L-leucine provided a N(α)-Fmoc-N-(benzoyloxy)-L-leucinamide in 90% yield. Deprotection of the benzoyl group (using 10 vol % NH4OH/MeOH) provided the N(α)-Fmoc-N-(hydroxy)-L-leucinamide in 87% yield. In general, the appended Fmoc group allowed for further elaboration of the N-hydroxy-N- (alkyl)amides using classic peptide-coupling methods. A practical synthetic strategy was developed, and racemization issues were addressed using diastereomeric Val-Leu derivatives. In addition, N-(hydroxy)thioamides were generated from the corresponding N-(benzoyloxy)thioamides. N- (Benzoyloxy)thioamides were obtained in moderate yields (53-76%) from the reaction of the corresponding N-(benzoyloxy)amides with Lawesson's reagent (i.e., 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide). In summary, this new technology allows for the introduction of either N- hydroxyamide or N-(hydroxy)thioamide linkages into pseudopeptide chains without racemization.