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CAS 206060-41-5

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N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-2-methoxy-L-phenylalanine

Description:
N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-2-methoxy-L-phenylalanine, commonly referred to as Fmoc-2-methoxy-L-phenylalanine, is a derivative of the amino acid phenylalanine, modified with a fluorenylmethoxycarbonyl (Fmoc) protecting group. This compound is characterized by its use in peptide synthesis, particularly in solid-phase peptide synthesis (SPPS), where the Fmoc group serves as a temporary protecting group for the amino functionality. The presence of the methoxy group on the phenylalanine side chain enhances the compound's hydrophobicity and can influence the overall conformation of peptides. The Fmoc group is stable under basic conditions, allowing for selective deprotection under mild acidic conditions, which is advantageous in multi-step synthesis. Additionally, the compound exhibits good solubility in organic solvents, making it suitable for various synthetic applications. Its structural features contribute to its utility in the development of peptide-based therapeutics and research in biochemistry and molecular biology.
Formula:C25H23NO5
InChI:InChI=1S/C25H23NO5/c1-30-23-13-7-2-8-16(23)14-22(24(27)28)26-25(29)31-15-21-19-11-5-3-9-17(19)18-10-4-6-12-20(18)21/h2-13,21-22H,14-15H2,1H3,(H,26,29)(H,27,28)/t22-/m0/s1
InChI key:InChIKey=CBCSNZJHURMDMO-QFIPXVFZSA-N
SMILES:C(OC(N[C@@H](CC1=C(OC)C=CC=C1)C(O)=O)=O)C2C=3C(C=4C2=CC=CC4)=CC=CC3
Synonyms:
  • L-Phenylalanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-2-methoxy-
  • N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-2-methoxy-L-phenylalanine
  • (s)-Fmoc-2-methoxyphenyLalanine
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