86060-90-4

Basic information

• Product Name: FMOC-PRO-OPFP
• Synonyms: N-(9-fluorenylmethoxycarbonyl)-L-proline pentafluorophenyl;Fmoc-L-proline pentafluorophenyl ester, N-(9-Fluorenylmethoxycarbonyl)-L-proline pentafluorophenyl ester;N-(9-Fluorenylmethoxycarbonyl)-L-proline pentafluorophenyl ester,97%;N-(Fluorenylmethoxycarbonyl)proline pentafluorophenyl ester;1,2-Pyrrolidinedicarboxylicacid, 1-(9H-fluoren-9-ylmethyl) 2-(pentafluorophenyl) ester, (2S)-;Fmoc-Pro-OP;(S)-Fmoc-pyrrolidine-2-carboxylic acid pentafluorophenyl ester;Fmoc-L-proline pentafluorophenyl ester≥ 99% (HPLC)
• CAS NO: 86060-90-4
• Molecular Formula: C₂₆H₁₈F₅NO₄
• Molecular Weight: 503.42
• Product Categories: Fmoc-Amino acid series;Amino Acids;Fmoc-Amino Acids and Derivatives
• Mol File: 86060-90-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: 127-129 °C(lit.)
• Boiling Point: 573.3 °C at 760 mmHg
• Flash Point: 300.5 °C
• Appearance: /Solid
• Density: 1.455 g/cm³
• Vapor Pressure: 3.77E-13mmHg at 25°C
• Refractive Index: 1.582
• Storage Temp.: 2-8°C
• BRN: 4731096
• CAS DataBase Reference: FMOC-PRO-OPFP(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-PRO-OPFP(86060-90-4)
• EPA Substance Registry System: FMOC-PRO-OPFP(86060-90-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 86060-90-4(Hazardous Substances Data)

Usage

Chemical Properties

White powder

InChI:InChI=1/C26H18F5NO4/c27-19-20(28)22(30)24(23(31)21(19)29)36-25(33)18-10-5-11-32(18)26(34)35-12-17-15-8-3-1-6-13(15)14-7-2-4-9-16(14)17/h1-4,6-9,17-18H,5,10-12H2/t18-/m0/s1

Upstream product

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

Downstream Products

• 482598-87-8 (S)-2-[(S)-1-((3R,4S)-1-Methoxycarbonylmethyl-2-oxo-4-phenyl-azetidin-3-yl)-3-methyl-butylcarbamoyl]-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester 
• 1334511-54-4 N-(9-fluorenylmethoxycarbonyl)-L-prolyl-N-ethyl-S-triphenyl-methyl-L-cysteine 
• 252570-76-6 C₇₄H₁₁₀N₂₀O₁₆S 
• 252570-77-7 C₇₄H₁₁₀N₂₀O₁₆S 
• 252570-75-5 C₆₆H₁₀₅N₁₉O₁₆S 
• 252570-74-4 C₇₁H₁₀₅N₁₉O₁₅S 
• 252570-79-9 C₈₂H₁₁₅N₂₁O₁₆S 
• 252570-73-3 C₆₉H₁₀₄N₁₈O₁₅S 
• 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.