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CAS 211637-74-0

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Fmoc-3-methyl-L-phenylalanine

Description:
Fmoc-3-methyl-L-phenylalanine is a derivative of the amino acid phenylalanine, modified with a 9-fluorenylmethoxycarbonyl (Fmoc) protecting group at the amino terminus. This compound is characterized by its incorporation of a methyl group at the 3-position of the phenyl ring, which influences its hydrophobicity and steric properties. The Fmoc group serves as a protective moiety that facilitates the synthesis of peptides by preventing unwanted reactions at the amino group during coupling reactions. Fmoc-3-methyl-L-phenylalanine is typically utilized in solid-phase peptide synthesis (SPPS) due to its stability under basic conditions and ease of removal under mild acidic conditions. The presence of the methyl group can enhance the conformational flexibility of peptides, potentially affecting their biological activity and interactions. This compound is of interest in the fields of medicinal chemistry and peptide research, where modifications to amino acids can lead to novel therapeutic agents or improved peptide-based drugs.
Formula:C25H23NO4
InChI:InChI=1/C25H23NO4/c1-16-7-6-8-17(13-16)14-23(24(27)28)26-25(29)30-15-22-20-11-4-2-9-18(20)19-10-3-5-12-21(19)22/h2-13,22-23H,14-15H2,1H3,(H,26,29)(H,27,28)/t23-/m1/s1
InChI key:InChIKey=NJXPSSISZLAXRE-QHCPKHFHSA-N
SMILES:C(OC(N[C@@H](CC1=CC(C)=CC=C1)C(O)=O)=O)C2C=3C(C=4C2=CC=CC4)=CC=CC3
Synonyms:
  • <span class="text-smallcaps">L</span>-Phenylalanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-3-methyl-
  • Fmoc-L-3-Methylphe
  • Fmoc-L-3-Methylphenylalanine
  • N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-3-methyl-<span class="text-smallcaps">L</span>-phenylalanine
  • N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-3-methyl-L-phenylalanine
  • L-Phenylalanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-3-methyl-
  • Fluorenylmethoxycarbonyl-L-3-methylphenylalanine
  • N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-(3-METHYL)-L-PHENYLALANINE
  • RARECHEM BK PT 0063
  • Fmoc-L-3-Me-Phe-OH
  • See more synonyms
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