125281-38-1

Basic information

• Product Name: FMOC-PRO-OPFP
• Synonyms: FMOC-PROLINE-OPFP;FMOC-PRO-OPFP;FMOC-L-PROLINE PENTAFLUOROPHENYL ESTER;FMOC-L-PRO-OPFP;N-ALPHA-FMOC-L-PROLINE PENTAFLUOROPHENYL ESTER;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-L-PROLINE PENTAFLUORPHENYL ESTER;N-(9-FLUORENYLMETHOXYCARBONYL)-L-PROLINE PENTAFLUOROPHENYL ESTER;(R)-1,2-Pyrrolidinedicarboxylic acid 1-(9H-fluoren-9-ylmethyl) 2-(pentafluorophenyl) ester
• CAS NO: 125281-38-1
• Molecular Formula: C₂₆H₁₈F₅NO₄
• Molecular Weight: 503.42
• Mol File: 125281-38-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 127-129 °C(lit.)
• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: FMOC-PRO-OPFP(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-PRO-OPFP(125281-38-1)
• EPA Substance Registry System: FMOC-PRO-OPFP(125281-38-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 125281-38-1(Hazardous Substances Data)

Usage

General Description

FMOC-PRO-OPFP is a chemical compound used in organic synthesis and peptide chemistry as a protecting group for the amino acid proline. It consists of an FMOC (9-fluorenylmethoxycarbonyl) group, which functions as a temporary protecting group for the amine group of proline, and an OPFP (orthogonal pentafluorophenyl) group, which provides additional protection for the carboxyl group. FMOC-PRO-OPFP is commonly used in peptide synthesis to control the reactivity of the proline amino acid, allowing for selective deprotection and subsequent functionalization. FMOC-PRO-OPFP is a valuable tool in the development of complex peptides and pharmaceuticals.

Upstream product

• 147-85-3 L-proline 
• 88744-04-1 (9-fluorenyl)methyl pentafluorophenyl carbonate 
• 771-61-9 2,3,4,5,6-pentafluorophenol 
• 103321-52-4 (S)-N-(fluoren-9-ylmethoxycarbonyl)prolyl chloride 
• 71989-31-6 Fmoc-Pro-OH 

Downstream Products

• 252570-73-3 C₆₉H₁₀₄N₁₈O₁₅S 
• 252570-79-9 C₈₂H₁₁₅N₂₁O₁₆S 
• 252570-74-4 C₇₁H₁₀₅N₁₉O₁₅S 
• 252570-75-5 C₆₆H₁₀₅N₁₉O₁₆S 
• 252570-77-7 C₇₄H₁₁₀N₂₀O₁₆S 
• 252570-76-6 C₇₄H₁₁₀N₂₀O₁₆S 
• 1334511-54-4 N-(9-fluorenylmethoxycarbonyl)-L-prolyl-N-ethyl-S-triphenyl-methyl-L-cysteine 
• 136553-76-9 cyclo-(D-Trp-D-Glu-Pro-D-Val-Leu-) 
• 248243-49-4 Fmoc-Pro-Thr(Ψ^Me,Mepro)-OH 
• 901139-37-5 N-9-fuorenylmethoxycarbonyl-(2S)-prolyl-(2S,4S)-4-methylprolyl-glycine benzyl ester 

Relevant articles and documents

Pseudo-prolines in cyclic peptides: Conformational stabilisation of cyclo[Pro-Thr(Ψ(Me,Me)pro)-Pro]

Linear peptide H-Pro-Thr(Ψ(Me,Me)pro)-Pro-OH containing a preformed cis-Pro-Thr(Ψ(Me,Me)pro) tertiary amide bond cyclises instantaneously and free of formation of oligomeric structures to the cyclic tripeptide cyclo- [Pro-Thr(Ψ(Me,Me)pro)-Pro]. Even at concentrations up to 10-1 M peptide, no oligomeric structures are detected by mass spectroscopy and HPLC. 2D 1H NMR studies of purified cyclotripeptide reveal the compound to exist in one single conformation with all peptide bonds in the cis conformation. These results indicate enhanced cyclisation tendencies of cis-amide bond containing peptides of short chain length.

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.