8.52067

Fmoc-Arg(Pbf)-OH

Novabiochem^®

• Synonym(s): Fmoc-Arg(Pbf)-OH, N-α-Fmoc-N ^G-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-L-arginine
• Empirical Formula (Hill Notation): C₃₄H₄₀N₄O₇S
• CAS Number: 154445-77-9
• Molecular Weight: 648.77
• UNSPSC Code: 12352209
• NACRES: NA.22
• MDL number: MFCD00235804

Properties

• Quality Segment: 400
• product line: Novabiochem^®
• assay: ≥98% (TLC), ≥99.0% (HPLC)
• form: powder
• reaction suitability: reaction type: Fmoc solid-phase peptide synthesis
• manufacturer/tradename: Novabiochem^®
• mp: >65 °C
• application(s): peptide synthesis
• functional group: Fmoc
• storage temp.: 2-8°C
• SMILES string: [S](=O)(=O)(N\C(=N\CCC[C@H](NC(=O)OCC3c4c(cccc4)c5c3cccc5)C(=O)O)\N)c1c(c2c(c(c1C)C)OC(C2)(C)C)C
• InChI: 1S/C34H40N4O7S/c1-19-20(2)30(21(3)26-17-34(4,5)45-29(19)26)46(42,43)38-32(35)36-16-10-15-28(31(39)40)37-33(41)44-18-27-24-13-8-6-11-22(24)23-12-7-9-14-25(23)27/h6-9,11-14,27-28H,10,15-18H2,1-5H3,(H,37,41)(H,39,40)(H3,35,36,38)/t28-/m0/s1
• InChI key: HNICLNKVURBTKV-NDEPHWFRSA-N

Description

General description

High purity Fmoc-protected amino acid for research and process production of peptides, with very low levels of dipeptide, free-amino acids and acetic acid impurities.
The standard derivative for the introduction of Arg in Fmoc SPPS ^[1,2]. The Pbf side-chain protecting group is removed with TFA approximately 1-2 times faster than Pmc.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 (852050).

Associated Protocols and Technical Articles
Fmoc-amino acids for Peptide Production
Cleavage and Deprotection Protocols for Fmoc SPPS


Literature references

^[1] L. A. Carpino, et al. (1993) Tetrahedron Lett., 34, 7829.
^[2] C. G. Fields, et al. (1993) Tetrahedron Lett., 34, 6661.

Application

• Syntheses of cyanophycin segments for investigations of cell-penetration: Describes the synthesis process and overall yields for steps from Fmoc-Arg(Pbf)-OH to Adp building blocks. (M Grogg, D Hilvert, D Seebach, 2019).
• Revisiting NO2 as Protecting Group of Arginine in Solid-Phase Peptide Synthesis: Compares the stability of Fmoc-Arg(Boc) 2 -OH with Fmoc-Arg(Pbf)-OH in solvents over time. (M Alhassan, A Kumar, J Lopez, F Albericio, 2020).
• Gene delivery of PAMAM dendrimer conjugated with the nuclear localization signal peptide originated from fibroblast growth factor 3: Discusses a conjugation reaction involving Fmoc-Arg(pbf)-OH in gene delivery systems. (J Lee, J Jung, YJ Kim, E Lee, JS Choi, 2014).

Analysis Note

Colour (visual): white to off white
Appearance of substance (visual): powder
Colour index (0,5 M in DMF): ≤ 150 Hazen
Identity (IR): passes test
Enantiomeric purity: ≥ 99.8 % (a/a)
Purity (HPLC): ≥ 99.0 % (a/a)
Fmoc-ß-Ala-OH (HPLC): ≤ 0.1 % (a/a)
Fmoc-ß-Ala-Arg(Pbf)-OH (HPLC): ≤ 0.1 % (a/a)
Fmoc-Arg(Pbf)-Arg(Pbf)-OH (HPLC): ≤ 0.1 % (a/a)
Fmoc-Arg-OH (HPLC): ≤ 0.1 % (a/a)
Assay free amino acid (HPLC): ≤ 0.2 %
Purity (TLC(011C)): ≥ 98 %
Purity (TLC(157B)): ≥ 98 %
Solubility (12,5 mmol in 25 ml DMF): clearly soluble
Assay (acidimetric): ≥ 90.0 %
Water (K. F.): ≤ 2.0 %
Ethyl acetate (HS-GC): ≤ 1.0 %
Acetate (IC): ≤ 0.02 %

To see the solvent systems used for TLC of Novabiochem^® products please click here.

Other Notes

Replaces: 04-12-1145

Legal Information

Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable