8.52034

Fmoc-Arg(Pmc)-OH

Novabiochem^®

• Synonym(s): Fmoc-Arg(Pmc)-OH, N-α-Fmoc-N ^G-(2,2,5,7,8-pentamethylchroman-6-sulfonyl)-L-arginine
• Empirical Formula (Hill Notation): C₃₅H₄₂N₄O₇S
• CAS Number: 119831-72-0
• Molecular Weight: 662.80
• MDL number: MFCD00065618
• UNSPSC Code: 12352209
• NACRES: NA.22

Properties

• Quality Segment: 200
• product line: Novabiochem^®
• assay: ≥85.0% (acidimetric), ≥98% (TLC), ≥98.0% (HPLC)
• form: powder
• reaction suitability: reaction type: Fmoc solid-phase peptide synthesis
• manufacturer/tradename: Novabiochem^®
• mp: 70-120 °C (decomposition)
• application(s): peptide synthesis
• functional group: amine
• storage temp.: 15-25°C
• SMILES string: [S](=O)(=O)(\N=C(\NCCC[C@H](NC(=O)OCC3c4c(cccc4)c5c3cccc5)C(=O)O)/N)c1c(c2c(c(c1C)C)OC(CC2)(C)C)C
• InChI: 1S/C35H42N4O7S/c1-20-21(2)31(22(3)23-16-17-35(4,5)46-30(20)23)47(43,44)39-33(36)37-18-10-15-29(32(40)41)38-34(42)45-19-28-26-13-8-6-11-24(26)25-12-7-9-14-27(25)28/h6-9,11-14,28-29H,10,15-19H2,1-5H3,(H,38,42)(H,40,41)(H3,36,37,39)/t29-/m0/s1
• InChI key: QTWZCODKTSUZJN-LJAQVGFWSA-N

Description

General description

An excellent derivative for the introduction of Arg in Fmoc SPPS. The Pmc group is removed by TFA in 1-3 hours ^[1,2,3]. For discussions on the side-reactions associated with the use of sulfonyl-based arginine protection, see ^{[4,5,6,7,8,9,10,11]}. In the synthesis of peptides containing both Arg and Trp, it is recommended that this derivative is used in conjunction with Fmoc-Trp(Boc)-OH (852050) ^[5,6,11].

Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS


Literature references

^[1] R. Ramage, et al. (1987) Tetrahedron Lett., 28, 2287.
^[2] J. Green, et al. (1988) Tetrahedron Lett., 29, 4341.
^[3] R. Ramage, et al. (1991) Tetrahedron Lett., 47, 6353.
^[4] P. Sieber (1987) Tetrahedron Lett., 28, 1637.
^[5] C. G. Fields, et al. (1993) Tetrahedron Lett., 34, 6661.
^[6] H. Choi, et al. (1993) Int. J. Peptide Protein Res., 42, 58.
^[7] A. Stierandova, et al. (1994) Int. J. Peptide Protein Res., 43, 31.
^[8] P. M. Fischer, et al. (1992) Int. J. Peptide Protein Res., 40, 19.
^[9] S. A. G. Beck, et al. (1991) Int. J. Peptide Protein Res., 38, 25.
^[10] E. Jaeger, et al. (1993) Biol. Chem. Hoppe-Seyler, 374, 349.
^[11] P. White in ′Peptides, Chemistry & Biology, Proc. 12th American Peptide Symposium′, J. A. Smith & J. E. Rivier (Eds), ESCOM, Leiden, 1992, pp. 537.

Analysis Note

Color (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Enantiomeric purity: ≥ 99.5 % (a/a)
Purity (TLC(011C)): ≥ 98 %
Purity (TLC(157B)): ≥ 98 %
Assay (HPLC, area%): ≥ 98.0 % (a/a)
Solubility (12,5 mmol in 25 ml DMF): clearly soluble
Assay (acidimetric): ≥ 85.0 %
Water (K. F.): ≤ 1.50 %

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

Other Notes

Replaces: 04-12-1073

Legal Information

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

Safety Information

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