Fmoc-L-Arg(Pbf)-OH Chemical Properties

Melting point:

132°C

alpha 

-5.5 º (c=1,DMF)

Density 

1.37±0.1 g/cm3(Predicted)

storage temp. 

Store at -15°C to -25°C.

solubility 

DMF (Sparingly), DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

3.83±0.21(Predicted)

color 

White to Off-White

optical activity

[α]/D -5.5±1.0°, c = 1 in DMF

BRN 

8302671

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)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

1

HS Code 

2935 90 90

HazardClass 

IRRITANT

MSDS

• Language:English Provider:SigmaAldrich

Fmoc-L-Arg(Pbf)-OH Usage And Synthesis

Chemical Properties

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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.

Uses

Fmoc-Arg(Pbf)-OH is a Fmoc-protected amino acid derivative that can be used to create arginine-containing peptides. The 2,2,4,6,7-pentamethyIdlhydrobenzofuran-5-sulfonyl group (Pbf) can be easily cleaved by trifluoroacetic acid (TFA).

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.

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.

Fmoc-L-Arg(Pbf)-OH(154445-77-9)Related Product Information

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