| Identification | More | [Name]
FMOC-Arg(Pbf)-OH | [CAS]
154445-77-9 | [Synonyms]
FMOC-(2,2,4,6,7-PENTAMETHYLDIHYDROBENZOFURAN-5-SULFONYL)-L-ARGININE
FMOC-ARGININE(PBF)-OH
FMOC-ARG(PBF)
FMOC-ARG(PBF)-OH
FMOC-L-ARGININE(PBF)
FMOC-L-ARG(PBF)
FMOC-L-ARG(PBF)-OH
FMOC-NG-PBF-L-ARGININE
FMOC-N-OMEGA-(2,2,4,6,7-PENTAMETHYLDIHYDROBENZOFURAN-5-SULFONYL)-L-ARGININE
N-ALPHA-9-FLUORENYLMETHOXYCARBONYL-NG-2,2,4,6,7-PENTAMETHYLDIHYDROBENZOFURAN-5-SULFONYL-L-ARGININE
N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-N-OMEGA-2,2,4,6,7-PENTAMETHYLDIHYDROBENZOFURAN-5-SULFONYL-L-ARGININE
N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-N'-2,2,4,6,7-PENTAMETHYLDIHYDROBENZOFURAN-5-SULFONYL-L-ARGININE
N ALPHA-9-FLUORENYLMETHYLOXYCARBONYL-N OMEGA-2,2,4,6,7-PENTAMETHYLDIHYDROBENZOFURAN-5-SULFONYL-L-ARGININE
N-ALPHA-FMOC-N'-2,2,4,6,7-PENTAMETHYLDIHYDROBENZOFURAN-5-SULFONYL-L-ARGININE
N-ALPHA-FMOC-N-G-2,2,4,6,7-PENTAMETHYLDIHYDROBENZOFURAN-5-SULFONYL-L-ALPHARGININE
N-ALPHA-FMOC-N-G-(2,2,4,6,7-PENTAMETHYLDIHYDROBENZOFURAN-5-SULFONYL)-L-ARGININE
N-ALPHA-FMOC-N-OMEGA-(2,2,4,6,7-PENTAMETHYLDIHYDROBENZOFURAN-5-SULFONYL)-L-ARGININE
N-ALPHA-FMOC-N-OMEGA-PBF-L-ARGININE
na-fmoc-ng-(2,2,4,6,7-pentamethyl-*dihydrobenzofu
Nα-Fmoc-Nω-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-L-arginine | [EINECS(EC#)]
604-954-4 | [Molecular Formula]
C34H40N4O7S | [MDL Number]
MFCD00235804 | [Molecular Weight]
648.77 | [MOL File]
154445-77-9.mol |
| Chemical Properties | Back Directory | [Appearance]
white powde | [Melting point ]
132°C | [alpha ]
-5.5 º (c=1,DMF) | [density ]
1.37±0.1 g/cm3(Predicted) | [storage temp. ]
−20°C
| [solubility ]
DMF (Sparingly), DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
3.83±0.21(Predicted) | [color ]
White to Off-White | [Optical Rotation]
[α]/D -5.5±1.0°, c = 1 in DMF | [Detection Methods]
HPLC,NMR | [BRN ]
8302671 | [Major Application]
peptide synthesis | [InChIKey]
YUMOVWGGELTYES-LJAQVGFWSA-N | [SMILES]
C(O)(=O)[C@H](CCCNC=NNS(C1=C(C)C(C)=C2OC(C)(C)CC2=C1C)(=O)=O)NC(OCC1C2=C(C=CC=C2)C2=C1C=CC=C2)=O | [CAS DataBase Reference]
154445-77-9(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
white powde | [Uses]
Fmoc-Arg(Pbf)-OH, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance. | [Definition]
Fmoc-Arg(Pbf)-OH is the standard derivative for the introduction of Arg in Fmoc SPPS. In the preparation of peptides containing both Arg and Trp, it is recommended that this derivative is used in conjunction with Fmoc-Trp(Boc)-OH. The Pbf side-chain protecting group is removed with TFA approximately 1-2 times faster than Pmc. TFA cleavage is best performed in the presence of a silane scavenger. The Pbf group of Fmoc-Arg(Pbf)-OH can be cleaved under moderate acid conditions. | [General Description]
Fmoc-Arg(Pbf)-OH, which is the most used building block for the introduction of Arg into SPPS, is the most expensive of all protected proteinogenic amino acids currently on the market and, like all Arg derivatives, it undergoes an important side-reaction upon activation. It is a highly problematic amino acid because of its ability to react intramolecularly, leading to its δ-lactam derivative. Arg is the key for the development of the so-called Cell-Penetrating Peptides[1].
| [Reactivity Profile]
The Pbf group of Fmoc-L-Arg(Pbf)-OH can be cleaved under moderate acid conditions. The amount of tryptophan alkylation is significantly reduced compared to other arginine side chain protecting groups, especially in the absence of scavengers. In one example reported in the literature, a peptide containing Arg(Pmc) was cleaved, and deprotected TFA resulted in 46% of the desired peptide.
| [reaction suitability]
reaction type: Fmoc solid-phase peptide synthesis | [Synthesis]
The synthesis method of Fmoc-L-Arg(Pbf)-OH: first esterifies the carboxyl group of arginine, then introduces a Boc group on the amino group to protect the amino group, introduces a Pbf group on the guanidine group, and removes the Boc group , saponification, and finally the introduction of the Fmoc group on the amino group. | [Solubility in organics]
≥64.9 mg/mL in DMSO; insoluble in H2O; ≥2.14 mg/mL in EtOH with ultrasonic | [References]
[1] Torre B, et al. Successful Development of a Method for the Incorporation of Fmoc-Arg(Pbf)-OH in Solid-Phase Peptide Synthesis using N Butylpyrrolidinone (NBP) as Solvent. Green Chemistry, 2020; 22: 3162-3169.
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| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
Alfa Aesar
|
| Telephone: |
400-6106006 |
| Website: |
http://chemicals.thermofisher.cn |
| Company Name: |
Energy Chemical
|
| Telephone: |
400-0056266 |
| Website: |
www.energy-chemical.com |
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