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8.52107

Sigma-Aldrich

Fmoc-ADMA(Pbf)-OH

≥98% (TLC), for peptide synthesis, Novabiochem®

Synonym(s):

Fmoc-ADMA(Pbf)-OH, N-α-Fmoc-N,N-ω-dimethyl-N-ωÆ-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-L-arginine

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About This Item

Empirical Formula (Hill Notation):
C36H44N4O7S
Molecular Weight:
676.82
UNSPSC Code:
12352209
NACRES:
NA.22

product name

Fmoc-ADMA(Pbf)-OH, Novabiochem®

Quality Level

200

product line

Novabiochem®

Assay

≥96.0% (HPLC)
≥98% (TLC)

form

powder

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

manufacturer/tradename

Novabiochem®

application(s)

peptide synthesis

functional group

Fmoc

storage temp.

15-25°C

General description

A derivative for the introduction of asymmetric dimethyl-arginine during Fmoc SPPS. Coupling can be carried out using any standard activation method. Removal of the Pbf protecting group occurs during the course of the TFA-mediated cleavage reaction. Ref [1] contains methods and protocols for the synthesis of arrays of histone-related peptides containing methylated arginine and lysine-residues.

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

Literature references

[1] S. Rothbart, et al. (2012) Methods Enzymol., 512, 107.

Application

  • Effect of arginine methylation on the RNA recognition and cellular uptake of Tat-derived peptides: Studies the use of Fmoc-ADMA(Pbf)-OH in modifying peptides to enhance their cellular uptake, relevant for drug delivery systems and therapeutic molecule development (JH Li et al., 2015).
  • Advances in Fmoc solid-phase peptide synthesis: Reviews the role of Fmoc-ADMA(Pbf)-OH in advancing peptide synthesis techniques, impacting the field of material science through the development of novel synthetic strategies and applications in biomaterials (R Behrendt, J Offer, 2016).

Linkage

Replaces: 04-12-1264

Analysis Note

Color (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Purity (TLC(157A)): ≥ 98 %
Enantiomeric purity: ≥ 99.0 % (a/a)
Assay (HPLC, area%): ≥ 96.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble
Water (K. F.): ≤ 2.0 %

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

Legal Information

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Articles

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Unnatural amino acids, the non-proteinogenic amino acids that either occur naturally or are chemically synthesized, are becoming more and more important as tools for modern drug discovery research.

Protocols

Building Blocks for Introducing Post-translational Modified Amino Acids

We provide an overview of our available reagents, together with recommendations and details of their use for synthesis of peptides containing post-translationally modified amino acids.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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