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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

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About This Item

Empirical Formula (Hill Notation):
C35H42N4O7S
CAS Number:
119831-72-0
Molecular Weight:
662.80
MDL number:
MFCD00065618
UNSPSC Code:
12352209
NACRES:
NA.22
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Quality Level

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

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Global Trade Item Number

SKUGTIN
852034010004027269086435
852034000504027269086411
852034002504027269086428