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4-[(AMinocarbonyl)aMino]-N-[(9H-fluoren-9-ylMethoxy)carbonyl]-D-phenylalanine

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4-[(AMinocarbonyl)aMino]-N-[(9H-fluoren-9-ylMethoxy)carbonyl]-D-phenylalanine Basic information

Product Name:
4-[(AMinocarbonyl)aMino]-N-[(9H-fluoren-9-ylMethoxy)carbonyl]-D-phenylalanine
Synonyms:
  • Fmoc-D-Aph(Cbm)-OH
  • 4-[(AMinocarbonyl)aMino]-N-[(9H-fluoren-9-ylMethoxy)carbonyl]-D-phenylalanine
  • FMoc-D-4-Aph(CbM)-OH
  • (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-ureidophenyl)propanoic acid
  • Fmoc-4-Aph(Trt)-OH
  • (9H-Fluoren-9-yl)MethOxy]Carbonyl D-Aph(Cbm)-OH
  • Fmoc-D-4-Aph(cbm)
  • (2R)-3-[4-(carbamoylamino)phenyl]-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanoic acid
CAS:
324017-22-3
MF:
C25H23N3O5
MW:
445.47
Mol File:
324017-22-3.mol
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4-[(AMinocarbonyl)aMino]-N-[(9H-fluoren-9-ylMethoxy)carbonyl]-D-phenylalanine Chemical Properties

Melting point:
163℃ (decomposition)
Boiling point:
699.1±55.0 °C(Predicted)
Density 
1.376±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
pka
3.82±0.10(Predicted)
form 
Solid
color 
White to Off-White
Stability:
Hygroscopic
InChIKey
HFPDOFBZCSQAEJ-JOCHJYFZSA-N
SMILES
C(O)(=O)[C@@H](CC1=CC=C(NC(N)=O)C=C1)NC(OCC1C2=C(C=CC=C2)C2=C1C=CC=C2)=O
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4-[(AMinocarbonyl)aMino]-N-[(9H-fluoren-9-ylMethoxy)carbonyl]-D-phenylalanine Usage And Synthesis

Uses

Fmoc-D-4-Aph(cBm)-OH is an amino acid derivative with an Fmoc protecting group, which can be used to synthesize biologically active peptide mimetics, such as Ac-D2Nal-D4Cpa-D3Pal-Ser-4Aph/4Amf(P)-D4Aph/D4Amf(Q)-Leu-ILys-Pro-DAla-NH2 with gonadotropin-releasing hormone (GnRH) antagonist activity[1].

References

[1] Guangcheng Jiang, et al. "GnRH antagonists: a new generation of long acting analogues incorporating p-ureido-phenylalanines at positions 5 and 6." Journal of medicinal chemistry 44.3 (2001): 453-467. DOI:10.1021/jm0003900

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