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CAS 86123-10-6

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Fmoc-D-Phenylalanine

Description:
Fmoc-D-Phenylalanine is a derivative of the amino acid phenylalanine, characterized by the presence of a 9-fluorenylmethoxycarbonyl (Fmoc) protecting group. This compound is commonly used in peptide synthesis, particularly in solid-phase peptide synthesis (SPPS), due to its ability to protect the amino group of the amino acid while allowing for further reactions. Fmoc-D-Phenylalanine is typically a white to off-white solid and is soluble in organic solvents such as dimethylformamide (DMF) and dimethyl sulfoxide (DMSO), but less soluble in water. The Fmoc group can be removed under basic conditions, facilitating the coupling of the protected amino acid to other amino acids in peptide chains. The D-configuration of phenylalanine in this compound indicates that it is the enantiomer that is not commonly found in natural proteins, making it useful for studying the effects of chirality in biological systems. Overall, Fmoc-D-Phenylalanine is a valuable reagent in the field of synthetic organic chemistry and biochemistry.
Formula:C24H20NO4
InChI:InChI=1/C24H21NO4/c26-23(27)22(14-16-8-2-1-3-9-16)25-24(28)29-15-21-19-12-6-4-10-17(19)18-11-5-7-13-20(18)21/h1-13,21-22H,14-15H2,(H,25,28)(H,26,27)/p-1/t22-/m1/s1
SMILES:c1ccc(cc1)C[C@H](C(=O)[O-])N=C(O)OCC1c2ccccc2c2ccccc12
Synonyms:
  • FMOC-D-Phenylalanine-OH
  • Fmoc-D-Phe-OH
  • N-(9-Fluorenylmethoxycarbonyl)-D-phenylalanine
  • Fmoc-D-Phc-OH
  • NALPHA-9-Fluorenylmethoxycarbonyl-D-phenylalanine
  • FmocAV21690
  • N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-phenylalanine
  • (2R)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-phenylpropanoate
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