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CAS 115520-21-3

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N(alpha)-fmoc-S-trityl-L-cysteine penta-fluorophenyl ester

Description:
N(alpha)-Fmoc-S-trityl-L-cysteine penta-fluorophenyl ester is a protected derivative of the amino acid cysteine, commonly used in peptide synthesis and research. This compound features a phenyl ester group, which enhances its stability and solubility, making it suitable for various chemical reactions. The Fmoc (9-fluorenylmethoxycarbonyl) group serves as a temporary protective group for the amino functionality, allowing for selective reactions at the thiol group of cysteine. The trityl group provides additional protection for the thiol, preventing unwanted reactions during synthesis. The presence of the penta-fluorophenyl ester moiety contributes to the compound's reactivity and solubility in organic solvents. This compound is typically utilized in the synthesis of peptides where cysteine residues are involved, particularly in the formation of disulfide bonds or in the introduction of specific functionalities. Its unique structural features make it a valuable intermediate in the field of medicinal chemistry and peptide design.
Formula:C43H30F5NO4S
InChI:InChI=1/C43H30F5NO4S/c44-35-36(45)38(47)40(39(48)37(35)46)53-41(50)34(49-42(51)52-24-33-31-22-12-10-20-29(31)30-21-11-13-23-32(30)33)25-54-43(26-14-4-1-5-15-26,27-16-6-2-7-17-27)28-18-8-3-9-19-28/h1-23,33-34H,24-25H2,(H,49,51)/t34-/m0/s1
InChI key:FDAUCYDVXIPBDR-UMSFTDKQSA-N
SMILES:c1ccc(cc1)C(c1ccccc1)(c1ccccc1)SC[C@@H](C(=O)Oc1c(c(c(c(c1F)F)F)F)F)N=C(O)OCC1c2ccccc2c2ccccc12
Synonyms:
  • Fmoc-Cys(Trt)-OPfp
  • N-alpha-(9-fluorenylmethyloxycarbonyl)-S-trityl-L-cysteine pentafluorphenyl ester
  • pentafluorophenyl N-[(9H-fluoren-9-ylmethoxy)carbonyl]-S-trityl-L-cysteinate
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