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CAS 138775-05-0

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Fmoc-N-methyl-D-phenylalanine

Description:
Fmoc-N-methyl-D-phenylalanine is a derivative of the amino acid phenylalanine, modified with a fluorenylmethyloxycarbonyl (Fmoc) protecting group and a methyl group on the nitrogen of 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 easily removed under basic conditions. The presence of the N-methyl group enhances the compound's lipophilicity and can influence the conformation and biological activity of the resulting peptides. Fmoc-N-methyl-D-phenylalanine is characterized by its stability under standard laboratory conditions, although it is sensitive to strong acids and bases. Its structure contributes to the overall hydrophobicity of peptides, making it useful in the design of bioactive compounds. Additionally, the D-configuration of phenylalanine can impart unique properties in terms of receptor binding and enzymatic resistance, making it a valuable building block in medicinal chemistry and peptide research.
Formula:C25H23NO4
InChI:InChI=1/C25H23NO4/c1-26(23(24(27)28)15-17-9-3-2-4-10-17)25(29)30-16-22-20-13-7-5-11-18(20)19-12-6-8-14-21(19)22/h2-14,22-23H,15-16H2,1H3,(H,27,28)/t23-/m1/s1
SMILES:CN([C@H](Cc1ccccc1)C(=O)O)C(=O)OCC1c2ccccc2c2ccccc12
Synonyms:
  • Fmoc-N-Me-D-Phe-Oh
  • Fmoc-N-Alpha-Methyl-D-Phenylalanine
  • Fmoc-D-Mephe-Oh
  • N-Alpha-(9-Fluorenylmethyloxycarbonyl)-N-Alpha-Methyl-D-Phenylalanine
  • N-Alpha-(9-Fluorenylmethoxycarbonyl)-N-Alpha-Methyl-Phenylalanine
  • N-Alpha-(9-Fluorenylmethoxycarbonyl)-N-Alpha-Methyl-D-Phenylalanine
  • N-Alpha-Fmoc-N-Alpha-Methyl-D-Phenylalanine
  • (2R)-2-(9H-fluoren-9-ylmethoxycarbonyl-methyl-amino)-3-phenyl-propanoic acid
  • Fmoc-D-N-Me-Phe-OH
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