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CAS 86069-87-6

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fmoc-L-tryptophan pentafluorophenyl ester

Description:
Fmoc-L-tryptophan pentafluorophenyl ester is a chemical compound that serves as a protected form of the amino acid tryptophan, commonly used in peptide synthesis. The "Fmoc" (9-fluorenylmethoxycarbonyl) group is a widely utilized protective group that allows for selective deprotection during the synthesis process. The pentafluorophenyl ester moiety enhances the reactivity of the carboxylic acid, facilitating the formation of peptide bonds. This compound is characterized by its stability under basic conditions and its ability to undergo cleavage under mild acidic conditions, making it suitable for various synthetic applications. It is typically a white to off-white solid and is soluble in organic solvents such as dichloromethane and dimethylformamide. The presence of fluorine atoms in the pentafluorophenyl group contributes to its unique electronic properties, which can influence the reactivity and selectivity in chemical reactions. Overall, Fmoc-L-tryptophan pentafluorophenyl ester is an important intermediate in the field of organic and medicinal chemistry, particularly in the synthesis of bioactive peptides.
Formula:C32H21F5N2O4
InChI:InChI=1/C32H21F5N2O4/c33-25-26(34)28(36)30(29(37)27(25)35)43-31(40)24(13-16-14-38-23-12-6-5-7-17(16)23)39-32(41)42-15-22-20-10-3-1-8-18(20)19-9-2-4-11-21(19)22/h1-12,14,22,24,38H,13,15H2,(H,39,41)/t24-/m0/s1
SMILES:c1ccc2c(c1)c1ccccc1C2COC(=N[C@@H](Cc1c[nH]c2ccccc12)C(=O)Oc1c(c(c(c(c1F)F)F)F)F)O
Synonyms:
  • Fmoc-Trp-OPfp
  • pentafluorophenyl N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-tryptophanate
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