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CAS 220497-81-4

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(R)-N-FMOC-3-Bromophenylalanine

Description:
(R)-N-FMOC-3-Bromophenylalanine is a derivative of the amino acid phenylalanine, modified to include a 3-bromo substituent on the aromatic ring and a fluorenylmethyloxycarbonyl (FMOC) protecting group on the amino group. This compound is typically used in peptide synthesis, particularly in solid-phase peptide synthesis (SPPS), where the FMOC group serves as a protective group that can be selectively removed under basic conditions. The presence of the bromine atom can enhance the compound's reactivity and facilitate further chemical modifications. As a chiral molecule, (R)-N-FMOC-3-Bromophenylalanine exhibits specific optical activity, which is important in the synthesis of biologically active peptides. Its structural characteristics contribute to its utility in research and pharmaceutical applications, particularly in the development of peptide-based drugs. The compound is generally handled with standard laboratory safety precautions, as with other chemical substances, to mitigate any potential hazards associated with its use.
Formula:C24H20BrNO4
InChI:InChI=1/C24H20BrNO4/c25-16-7-5-6-15(12-16)13-22(23(27)28)26-24(29)30-14-21-19-10-3-1-8-17(19)18-9-2-4-11-20(18)21/h1-12,21-22H,13-14H2,(H,26,29)(H,27,28)/t22-/m1/s1
SMILES:c1ccc2c(c1)c1ccccc1C2COC(=N[C@H](Cc1cccc(c1)Br)C(=O)O)O
Synonyms:
  • Fmoc-D-3-Bromophenylalanine
  • Fmoc-3-Bromo-D-phenylalanine
  • Fmoc-D-Phe(3-Br)-OH
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