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Fmoc-norArg(pbf)-OH

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Fmoc-norArg(pbf)-OH Basic information

Product Name:
Fmoc-norArg(pbf)-OH
Synonyms:
  • (2S)-4-[[amino-[(2,2,4,6,7-pentamethyl-3~{H}-1-benzofuran-5-yl)sulfonylamino]methylidene]amino]-2-(9~{H}-fluoren-9-ylmethoxycarbonylamino)butanoic acid
  • (2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-{N'-[(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)sulfonyl]carbamimidamido}butanoic acid
  • Fmoc-norArg(pbf)-OH
  • Butanoic acid, 4-[[[[(2,3-dihydro-2,2,4,6,7-pentamethyl-5-benzofuranyl)sulfonyl]amino]iminomethyl]amino]-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-, (2S)-
  • (2S)-4-[[[[(2,3-Dihydro-2,2,4,6,7-pentamethyl-5-benzofuranyl)sulfonyl]amino]iminomethyl]amino]-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]butanoic acid
  • (S,E)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-(N'-((2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-yl)sulfonyl)formohydrazonamido)butanoic acid
  • (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-(3-((2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-yl)sulfonyl)guanidino)butanoic acid
  • (S)-2-(Fmoc-amino)-4-[[amino(2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-sulfonamido)methylene]amino]butanoic Acid
CAS:
1313054-32-8
MF:
C33H38N4O7S
MW:
634.74
Product Categories:
  • amino acid
  • amino acids
Mol File:
1313054-32-8.mol
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Fmoc-norArg(pbf)-OH Chemical Properties

Density 
1.38±0.1 g/cm3(Predicted)
storage temp. 
under inert gas (nitrogen or Argon) at 2–8 °C
pka
3.75±0.10(Predicted)
InChIKey
FWOIXFWITXCUKI-NDEPHWFRSA-N
SMILES
C(O)(=O)[C@@H](NC(OCC1C2=C(C=CC=C2)C2=C1C=CC=C2)=O)CCNC=NNS(C1=C(C)C(C)=C2OC(C)(C)CC2=C1C)(=O)=O
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Fmoc-norArg(pbf)-OH Usage And Synthesis

Chemical Properties

The IUPAC Name of Fmoc-norArg(pbf)-OH is rac-(R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(3-((2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-yl)sulfonyl)guanidino)propanoic acid. Pbf is 2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl.
In addition, conjugation of Arg-containing peptides is difficult due to the steric hindrance of Pbf in a side chain as a protecting group, resulting in low peptide yield or even synthesis failure[1].

References

[1] Keiichi Yamada . “Efficient solid-phase synthesis of cyclic RGD peptides under controlled microwave heating.” Tetrahedron Letters 53 9 (2012): Pages 1066-1070.

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