86060-88-0

Basic information

• Product Name: FMOC-LEU-OPFP
• Synonyms: N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-L-LEUCINE PENTAFLUORPHENYL ESTER;N-ALPHA-FMOC-L-LEUCINE PENTAFLUOROPHENYL ESTER;FMOC-LEUCINE-OPFP;FMOC-LEU-OPFP;FMOC-L-LEU-OPFP;FMOC-L-LEUCINE PENTAFLUOROPHENYL ESTER;NALPHA-9-Fluorenylmethoxycarbonyl-L-leucine pentafluorophenyl ester;N-(9-fluorenylmethoxycarbonyl)-L-leucine pentafluorophenyl
• CAS NO: 86060-88-0
• Molecular Formula: C₂₇H₂₂F₅NO₄
• Molecular Weight: 519.46
• Product Categories: Amino Acid Derivatives;Amino Acids;Fmoc-Amino Acids and Derivatives;Fmoc-Amino acid series
• Mol File: 86060-88-0.mol

Chemical Properties

• Melting Point: 101-115°C
• Boiling Point: 596.3 °C at 760 mmHg
• Flash Point: 314.5 °C
• Appearance: White/Powder
• Density: 1.35 g/cm³
• Refractive Index: 1.549
• Storage Temp.: 2-8°C
• PKA: 10.32±0.46(Predicted)
• BRN: 4731726
• CAS DataBase Reference: FMOC-LEU-OPFP(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-LEU-OPFP(86060-88-0)
• EPA Substance Registry System: FMOC-LEU-OPFP(86060-88-0)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 86060-88-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Chemistry:
Fmoc-Leu-OPfp is used as a building block for peptide synthesis, allowing for the stepwise construction of complex peptide structures. The protective Fmoc group ensures that the Leucine amino acid does not react prematurely, while the OPfp group facilitates the coupling process, making it an essential component in the synthesis of various pharmaceutical compounds.
Used in Biological Research:
In the field of biological research, Fmoc-Leu-OPfp is used as a reagent for the synthesis of peptides that can be used as probes, inhibitors, or therapeutic agents. The controlled synthesis of these peptides is vital for understanding their biological functions and potential applications in medicine.
Used in Drug Development:
Fmoc-Leu-OPfp is used as a key component in the development of new drugs, particularly in the synthesis of peptide-based drugs. Fmoc-Leu-OPfp's ability to facilitate the coupling of amino acids in a controlled manner is crucial for the creation of novel therapeutic agents with specific biological activities.
Used in Diagnostic Applications:
Fmoc-Leu-OPfp can be used in the synthesis of diagnostic peptides, which are essential for the development of diagnostic tests and assays. These peptides can serve as markers or probes, helping to identify and measure the presence of specific biological molecules in samples.
Used in Agricultural Biotechnology:
In agricultural biotechnology, Fmoc-Leu-OPfp may be used in the synthesis of peptides that can be employed as plant growth regulators, pest control agents, or in the development of genetically modified crops with enhanced traits. Fmoc-Leu-OPfp's role in peptide synthesis is crucial for creating these innovative agricultural products.

InChI:InChI=1/C27H22F5NO4/c1-13(2)11-19(26(34)37-25-23(31)21(29)20(28)22(30)24(25)32)33-27(35)36-12-18-16-9-5-3-7-14(16)15-8-4-6-10-17(15)18/h3-10,13,18-19H,11-12H2,1-2H3,(H,33,35)/t19-/m0/s1

Upstream product

• 35661-60-0 Fmoc-Leu-OH 
• 96157-57-2 bis(pentafluorophenyl)sulfite 
• 61-90-5 L-leucine 
• 88744-04-1 (9-fluorenyl)methyl pentafluorophenyl carbonate 
• 771-61-9 2,3,4,5,6-pentafluorophenol 

Downstream Products

• 86061-08-7 (S)-N-((S)-1-Carbamoyl-2-phenyl-ethyl)-3-[(S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methyl-pentanoylamino]-succinamic acid tert-butyl ester 
• 137565-20-9 Lys-Asp-Ser-Phe-Val-Gly-Leu-Met-NH₂ 
• 139551-83-0 (S)-(9H-fluoren-9-yl)methyl (1-hydroxy-4-methylpentan-2-yl)carbamate 
• 252570-73-3 C₆₉H₁₀₄N₁₈O₁₅S 
• 252570-79-9 C₈₂H₁₁₅N₂₁O₁₆S 
• 252570-74-4 C₇₁H₁₀₅N₁₉O₁₅S 
• 252570-75-5 C₆₆H₁₀₅N₁₉O₁₆S 
• 252570-77-7 C₇₄H₁₁₀N₂₀O₁₆S 
• 252570-76-6 C₇₄H₁₁₀N₂₀O₁₆S 
• 1207188-92-8 N-(9-fluorenylmethoxycarbonyl)-L-leucyl-N-ethyl-S-triphenylmethyl-L-cysteine 
• 1146758-19-1 C₅₃H₇₁Cl₆N₉O₂₂S₂ 
• 86091-60-3 (S)-N-((S)-1-Carbamoyl-2-phenyl-ethyl)-3-{(S)-2-[(S)-2-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-acetylamino]-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoylamino}-succinamic acid tert-butyl ester 
• 86091-61-4 9-Fluorenylmethyloxycarbonyl-glycyl-L-tryptophyl-L-leucyl-L-aspartyl-L-phenylalaninamide 
• 86061-09-8 (S)-N-((S)-1-Carbamoyl-2-phenyl-ethyl)-3-{(S)-2-[(S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoylamino}-succinamic acid tert-butyl ester 

Relevant articles and documents

A new facile one-pot preparation of pentafluorophenyl (Pfp) and 3,4-dihydro-4-oxo-1,2,3-benzotriazine-3-yl (Dhbt) esters of Fmoc amino acids

A new one-pot procedure for the preparation of pentafluorophenyl and 3,4-dihydro-4-oxo-1,2,3-benzotriazine-3-yl esters of Nα-9-fluorenylmethyloxycarbonyl amino acids bearing no side chain protecting groups is described. The method gives the desired activated esters in high yield and purity without use of the highly allergenic DCC.

Bis(pentaluorophenyl) sulfite - A new reagent for the synthesis of activated pentafluorophenyl esters of N-protected amino acids

A method was proposed for the preparation of bis(perfluorophenyl) sulfite, an effective new reagent for the synthesis of pentafluorophenyl esters of N-protected amino acids without racemization.

9-Fluorenylmethyl Pentafluorophenyl Carbonate as a Useful Reagent for the Preparation of N-9-Fluorenylmethyloxycarbonylamino Acids and their Pentafluorophenyl Esters

9-Fluorenylmethyl pentafluorophenyl carbonate is a useful reagent for the efficient, side reaction-free introduction of N-9-fluorenylmethyloxycarbonyl protecting group into amino acids and for the subsequent preparation of their pentafluorophenyl esters.Some new compounds of both types are described.