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CAS 478183-67-4

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N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-3-iodo-D-phenylalanine

Description:
N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-3-iodo-D-phenylalanine, commonly referred to as Fmoc-3-iodo-D-Phe, is a synthetic amino acid derivative used primarily in peptide synthesis and research. This compound features a fluorenylmethoxycarbonyl (Fmoc) protecting group, which is widely utilized in solid-phase peptide synthesis due to its stability under basic conditions and ease of removal under acidic conditions. The presence of the iodine atom at the 3-position of the phenylalanine side chain enhances its reactivity and can facilitate various coupling reactions. The Fmoc group also contributes to the compound's hydrophobic characteristics, influencing solubility and interaction with other molecules. This compound is typically used in the synthesis of peptides that require specific stereochemistry or functionalization, making it valuable in the development of pharmaceuticals and bioconjugates. Its unique structural features allow for the exploration of peptide properties and functions in biological systems.
Formula:C24H20INO4
InChI:InChI=1S/C24H20INO4/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
InChI key:InChIKey=SSKOJXLIQFVOGC-JOCHJYFZSA-N
SMILES:C(OC(N[C@H](CC1=CC(I)=CC=C1)C(O)=O)=O)C2C=3C(C=4C2=CC=CC4)=CC=CC3
Synonyms:
  • D-Phenylalanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-3-iodo-
  • N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-3-iodo-D-phenylalanine
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