GLPBio

Fmoc-Arg(Pbf)-OH

Catalog No.: GA11082Purity:>99.50%
Fmoc-Arg(Pbf)-OH is a protected amino acid derivative of arginine.

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Fmoc-Arg(Pbf)-OH
Cas No.: 154445-77-9
25gIn Stock
$70.00
1
100gIn Stock
$280.00
1

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    610, 366–372 (2022)
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    187(9):2288-2304 (2024)
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    183(7):1867-1883 (2020)
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Beschreibung (Description)

Fmoc-Arg(Pbf)-OH is a protected amino acid derivative of arginine [1]. Fmoc-Arg(Pbf)-OH is a similar compound to Gly-Pro and Arg(Pbf)-OH, both of which are dipeptide structural units. The Pbf group of Fmoc-Arg(Pbf)-OH can be cleaved under moderately acidic conditions [2]. Fmoc-Arg(Pbf)-OH has been used in the solid-phase synthesis of peptides containing L-arginine [3].

References:
[1] Beatriz G, 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(10): 3162-3169.
[2] Fields C G, Fields G B. Minimization of tryptophan alkylation following 9-fluorenylmethoxycarbonyl solid-phase peptide synthesis[J]. Tetrahedron letters, 1993, 34(42): 6661-6664.
[3] Boullet H, Bentot F, Hequet A, et al. Small antimicrobial peptide with in vivo activity against sepsis[J]. Molecules, 2019, 24(9): 1702.
[4] Karlsen, E.A.; Stensen, W.; Juskewitz, E.; Svenson, J.; Berglin, M.; Svendsen, J.S.M. Anti-Colonization Effect of Au Surfaces with Self-Assembled Molecular Monolayers Functionalized with Antimicrobial Peptides on S. epidermidis. Antibiotics 2021, 10, 1516.

Protokoll (Protocol)

Loading and coupling of Rink Amide resin[1]:

1. Rink Amide HL (0.98mmol/g) is expanded at 70°C for 20 minutes.

2. 20% piperidine solution is added in DMF to remove the Fmoc groups from the resin.

3. Fmoc amino acids (4.00eq.) are coupled with O-(benzotriazol-1-yl)-N,N,N′,N′-tetrafluorophosphorodimethylurea (HBTU, 3.92eq.), 1-hydroxybenzotriazole hydrate (HOBt, 4.00eq.), and N,N-dipropylacetamide (DIPEA, 8.0eq.).

4. Before coupling the next amino acid, the N-terminal Fmoc is removed with piperidine (20%) in DMF.

5. Fmoc-Phe-OH (4.0eq.) and Fmoc-Trp(Boc)-OH (4.0eq.) are coupled at 70°C for 5 minutes, Fmoc-Bip-OH (4.0eq.) is coupled at 75°C. Fmoc-Arg(Pbf)-OH (4.0eq.) is coupled at room temperature for 60 minutes, and Fmoc-Lys(N3) is coupled at room temperature for 16 hours. N3-PEG200-COOH (4.0eq.) or N3-PEG400-COOH (4.0eq.) is coupled with HBTU (3.92eq.) and HOBt (4.0eq.) for 16 hours at room temperature.

6. After the final coupling, the non-PEGylated peptide is removed from the Fmoc groups, the resin is washed with MeOH and DCM, and then placed in a drying machine overnight.

This protocol only provides a guideline, and should be modified according to your specific needs

References:
[1] Karlsen, E.A.; Stensen, W.; Juskewitz, E.; Svenson, J.; Berglin, M.; Svendsen, J.S.M. Anti-Colonization Effect of Au Surfaces with Self-Assembled Molecular Monolayers Functionalized with Antimicrobial Peptides on S. epidermidis. Antibiotics 2021, 10, 1516.

Produktdokumente (Product Documents)

Purity:>99.50%Appearance:A solid

Chemische Eigenschaften (Chemical Properties)

CAS-Nr.
154445-77-9
Chemischer Name
(2S)-5-[[amino-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonylamino]methylidene]amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic acid
SMILES
CC1=C2C(=C(C(=C1C)S(=O)(=O)NC(=NCCCC(C(=O)O)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35)N)C)CC(O2)(C)C
Summenformel
C34H40N4O7S
Molekulargewicht
648.8
Löslichkeit
≥ 64.9mg/mL in DMSO, ≥ 2.14 mg/mL in EtOH with ultrasonic
Lagerung
Desiccate at -20°C
Allgemeine Hinweise
Wählen Sie anhand der Löslichkeitsdaten des Produkts ein geeignetes Lösungsmittel. Aliquotieren Sie die Stammlösung nach der Herstellung, um wiederholte Gefrier-Auftau-Zyklen zu vermeiden.
Verwenden Sie Stammlösungen bei Lagerung bei -80°C innerhalb von 6 Monaten bzw. bei -20°C innerhalb von 1 Monat.
Zur Verbesserung der Löslichkeit das Röhrchen auf 37°C erwärmen und für eine angemessene Dauer beschallen.
Versandbedingungen
Evaluierungsmuster werden mit Kühlakkus versandt. Andere verfügbare Größen werden bei Raumtemperatur oder auf Anfrage mit Kühlakkus versandt.

Rechner (Calculators)Molarität / Verdünnung / Molekulargewicht / Einheitenumrechnung / In-vivo-Formulierung / Löslichkeit

g/mol

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