ChemicalBook > CAS DataBase List > Fmoc-L-Arg(Pbf)-OH

Fmoc-L-Arg(Pbf)-OH

Product Name
Fmoc-L-Arg(Pbf)-OH
CAS No.
154445-77-9
Chemical Name
Fmoc-L-Arg(Pbf)-OH
Synonyms
FMOC-ARG(PBF);FMOC-L-ARG(PBF)-OH;Fomc-Arg(pbf)-OH;-[(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)sulfonyl]carbamimidamido}pentanoic acid;FMOC-L-ARG(PBF);FMOC-ARG(PBF)-OH;Fmoc-Arq(Pbf)-OH;Fmoc Pbf Arginine;Fmoc-Arg(Pbf) ,98%;Fmoc-Pbf-L-arginine
CBNumber
CB7764987
Molecular Formula
C34H40N4O7S
Formula Weight
648.77
MOL File
154445-77-9.mol
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Fmoc-L-Arg(Pbf)-OH Property

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)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
1
HS Code 
2935 90 90
HazardClass 
IRRITANT
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P322Specific measures (see …on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.52067
Product name
Fmoc-Arg(Pbf)-OH
Purity
Novabiochem?
Packaging
5G
Price
$65.6
Updated
2024/03/01
Sigma-Aldrich
Product number
8.52067
Product name
Fmoc-Arg(Pbf)-OH
Purity
Novabiochem?
Packaging
25g
Price
$219
Updated
2024/03/01
Sigma-Aldrich
Product number
8.52067
Product name
Fmoc-Arg(Pbf)-OH
Purity
Novabiochem?
Packaging
100g
Price
$583
Updated
2024/03/01
Sigma-Aldrich
Product number
8.52067
Product name
Fmoc-Arg(Pbf)-OH
Purity
Novabiochem?
Packaging
250g
Price
$1170
Updated
2024/03/01
Sigma-Aldrich
Product number
8.52067
Product name
Fmoc-Arg(Pbf)-OH
Purity
Novabiochem?
Packaging
1kg
Price
$3070
Updated
2024/03/01
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Fmoc-L-Arg(Pbf)-OH Chemical Properties,Usage,Production

Chemical Properties

white powde

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 Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Fmoc-L-Arg(Pbf)-OH manufacturers

Sichuan HongRi Pharma-Tech Co.,Ltd
Product
Fmoc-L-Arg(Pbf)-OH 154445-77-9
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
1T+
Release date
2023-09-27
HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
Fmoc-L-Arg(Pbf)-OH 154445-77-9
Price
US $999.00-800.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000
Release date
2024-08-22
HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
Fmoc-L-Arg(Pbf)-OH 154445-77-9
Price
US $100.00-75.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000
Release date
2024-08-22

154445-77-9, Fmoc-L-Arg(Pbf)-OHRelated Search:

FMOC-b-Ala-OH ARGINASE Fmoc-Asp(OtBu)-OH N-(9-Fluorenylmethoxycarbonyloxy)succinimide Fmoc-Lys(Boc)-OH 9-Fluorenylmethyl chloroformate Fmoc-Phe-OH N-Boc-N'-nitro-L-arginine Sulfuryl chloride Nalpha-Fmoc-Ndelta-trityl-L-glutamine L(+)-Arginine L-Fmoc-Aspartic acid alpha-tert-butyl ester FMOC-ASU-OH FMOC-ARG(ME,PBF)-OH FMOC-THR(TBU)-OL FMOC-N-METHYL-TRANEXAMIC ACID Fmoc-L-Tyr(propargyl)-OH Fmoc-Gly-OH

  • na-fmoc-ng-(2,2,4,6,7-pentamethyl-*dihydrobenzofu
  • -[(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)sulfonyl]carbamimidamido}pentanoic acid
  • FMOC-N-OMEGA-(2,2,4,6,7-PENTAMETHYLDIHYDROBENZOFURAN-5-SULFONYL)-L-ARGININE
  • FMOC-NG-PBF-L-ARGININE
  • FMOC-ARG(PBF)
  • FMOC-ARGININE(PBF)-OH
  • FMOC-ARG(PBF)-OH
  • FMOC-(2,2,4,6,7-PENTAMETHYLDIHYDROBENZOFURAN-5-SULFONYL)-L-ARGININE
  • FMOC-L-ARGININE(PBF)
  • FMOC-L-ARG(PBF)
  • FMOC-L-ARG(PBF)-OH
  • FMOC-L-ARG(PBF)-OH(154445-77-9)
  • pentaMethyldihydrobenzofuran-5-sulfonyl)-L-arginine
  • Nalpha-Fmoc-Nomega-Pbf-L-arginine Fmoc-Arg(Pbf)-OH
  • N^a-FMoc-N^w-(2,2,4,6,7-pentaMethyl-2,3-dihydrobenzo[b]furan-5-ylsulfonyl)-L-arginine, 98%
  • Na-FMoc-Nw-Pbf-L-arginine
  • N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-N-OMEGA-2,2,4,6,7-PENTAMETHYLDIHYDROBENZOFURAN-5-SULFONYL-L-ARGININE
  • N-ALPHA-9-FLUORENYLMETHOXYCARBONYL-NG-2,2,4,6,7-PENTAMETHYLDIHYDROBENZOFURAN-5-SULFONYL-L-ARGININE
  • N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-N'-2,2,4,6,7-PENTAMETHYLDIHYDROBENZOFURAN-5-SULFONYL-L-ARGININE
  • N-ALPHA-FMOC-N'-2,2,4,6,7-PENTAMETHYLDIHYDROBENZOFURAN-5-SULFONYL-L-ARGININE
  • N-ALPHA-FMOC-N-G-2,2,4,6,7-PENTAMETHYLDIHYDROBENZOFURAN-5-SULFONYL-L-ALPHARGININE
  • N-ALPHA-FMOC-N-G-(2,2,4,6,7-PENTAMETHYLDIHYDROBENZOFURAN-5-SULFONYL)-L-ARGININE
  • N-ALPHA-FMOC-N-OMEGA-PBF-L-ARGININE
  • N-ALPHA-FMOC-N-OMEGA-(2,2,4,6,7-PENTAMETHYLDIHYDROBENZOFURAN-5-SULFONYL)-L-ARGININE
  • N ALPHA-9-FLUORENYLMETHYLOXYCARBONYL-N OMEGA-2,2,4,6,7-PENTAMETHYLDIHYDROBENZOFURAN-5-SULFONYL-L-ARGININE
  • N<sup>α</sup>-FMoc-N<sup>ω</sup>-(2,2,4,6,7-pentaMethyldihydrobenzofuran-5-sulfonyl)-L-arginine
  • (S)-2-((((9H-Fluoren-9-yl)Methoxy)carbonyl)aMino)-5-(3-((2,2,4,6,7-pentaMethyl-2,3-dihydrobenzofuran-5-yl)sulfonyl)guanidino)pentanoic acid
  • L-Ornithine, N5-[[[(2,3-dihydro-2,2,4,6,7-pentamethyl-5-benzofuranyl)sulfonyl]amino]iminomethyl]-N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-
  • Nα-Fmoc-Nω-(2,2,4,6,7-pentamethyldihydro-benzofuran-5-sulfonyl)-L-arginine≥ 99.5% (HPLC, Chiral purity)
  • Nalpha-Fmoc-Nomega-(2,2,4,6,7-pentamethyl-2,3-dihydrobenzo[b]furan-5-ylsulfonyl)-L-arginine
  • Nα-[(9H-Fluoren-9-ylmethoxy)carbonyl]-Nω-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-L-arginine
  • (9H-Fluoren-9-yl)MethOxy]Carbonyl Arg(Pbf)-OH
  • Fomc-Arg(pbf)-OH
  • N5-[[[(2,3-Dihydro-2,2,4,6,7-pentamethyl-5-benzofuranyl)sulfonyl]amino]iminomethyl]-N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-ornithine
  • FMoc-Arg(Pbf)-OH >=98.0% (HPLC)
  • Nalpha-Fmoc-Nomega-(2,2,4,6,7-pentamethyl-2,3-dihydrobenzo[b]furan)-5-sulfonyl-L-arginine
  • (2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-5-{N'-[(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)sulfonyl]carbamimidamido}pentanoic acid
  • N<SUB>α</SUB>-Fmoc-Nω-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-L-arginine
  • N<SUB>α</SUB>-Fmoc-Nω-Pbf-L-arginine
  • Na-Fmoc-Ng-2,2,4,6,7-pentamethyl-dihydrobenzofuran-5-sulfonyl-L-arginine
  • N-α-Fmoc-N-ω-2,2,4,6,7-pentamethyldihydro
  • NA-FMOC-NG-(2,2,4,6,7-PENTAMETHYL-*DIHYD ROBENZOFURA
  • Fmoc-Arq(Pbf)-OH
  • Nα-Fmoc-Nω-Pbf-L-Arginine
  • NALPHA-9-Fluorenylmethoxycarbonyl-NOMEGA-(2,2,4,6,7-pentamethyldihydrobenzo
  • N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine
  • N-Fmoc-Ng-2,2,4,6,7-pentamethyldihydrobenzofuran-5- sulfonyl-D-Arginine
  • FMOC-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine
  • Nα-Fmoc-Nω-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-L-arginine, Nα-Fmoc-Nω-Pbf-L-arginine
  • Nα-Fmoc-Nω-Pbf-L-arginine ,98%
  • Fmoc-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-L-argin
  • fmoc-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfon
  • FMoc-Arg(Pbf)-OH N-α-FMoc-N-ω-2,2,4,6,7-pentaMethyldihydro
  • Nalpha-[(9H-Fluoren-9-ylMethoxy)carbonyl]-NoMega-(2,2,4,6,7-pentaMethyldihydrobenzofuran-5-sulfonyl)-L-arginine
  • Fmoc-Arg(Pbf) ,98%
  • nα-fmoc-nω-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-l-arginine
  • Nalpha-9-Fluorenylmethyloxycarbonyl-Nw-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine
  • L-ARGININE-N-FMOC, PBF (CHEMICAL PURITY 90-95%)