Fmoc d phe oh

Manufactured by Iris Biotech

Sourced in Germany

Fmoc–D–Phe–OH is a chemical compound used as a building block in solid-phase peptide synthesis. It is a protected amino acid with the Fmoc (fluorenylmethyloxycarbonyl) protecting group on the amino terminus and the carboxylic acid functional group on the side chain.

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3 protocols using fmoc d phe oh

Synthesis and Characterization of c(RGDfC) Peptide

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Ultrapure water (Mili-Q, r > 18 MΩ·cm) was used in all the experiments. Acetonitrile (ACN), acetic acid (AcOH), dicholoromethane (DCM), diethyl ether (Et₂O), dimethylformamide (DMF), chloroform (CHCl₃), and methanol (MeOH) were obtained from Sigma-Aldrich (Saint-Quentin Fallavier, France) and were used without further purification.
The synthesis of c(RGDfC) peptide required N,N,N′,N′-tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate (HBTU) (Iris Biotech GmbH, Germany) and acetic anhydride (Sigma-Aldrich, Saint-Quentin Fallavier, France), and N–methylmorpholine (NMM), N–methylpyrrolidinone (NMP), N,N-diisopropylethylamine (DIPEA), piperidine and tetrakis(triphenylphosphine)palladium(0) (Pd(PPh₃)₄) (Alfa Aesar, Haverhill, MA, USA) as reagents. Fmoc–L–Asp–OAll, Fmoc–Gly–OH, Fmoc–L–Arg(Pbf)–OH, Fmoc–L–Cys (Trt)–OH, Fmoc–D–Phe–OH and 2CTC resin (2-chlorotrityl chloride resin, 100–200 mesh, 1.0–2.0 mmol/g loading) were obtained from Iris Biotech GmbH (Marktredwitz, Germany). Trifluoroacetic acid (TFA) was purchased from Sigma-Aldrich (Saint-Quentin Fallavier, France) and triisopropylsilane (TIPS) from Alfa Aesar (Haverhill, MA, USA).
The synthesis of DSPE-PEG₅₀₀₀-c(RGDfC) required DSPE-PEG₅₀₀₀-Mal (≥95%, Biochempeg Scientific Inc., Watertown, MA, USA), and phosphate-buffered saline (pH 7.4) and 1 kDa dialysis membrane (Sigma-Aldrich, Saint-Quentin Fallavier, France).

Ben Mihoub A., Elkhoury K., Nel J., Acherar S., Velot E., Malaplate C., Linder M., Latifi S., Kahn C., Huguet M., Yen F.T, & Arab-Tehrany E. (2023). Neuroprotective Effect of Curcumin-Loaded RGD Peptide-PEGylated Nanoliposomes. Pharmaceutics, 15(12), 2665.

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Synthesis and Characterization of Peptide Derivatives

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TFA was from Alfa Aesar (Haverhill, MA, USA); ACCA from Bruker (Ettlingen, Germany); butanoic acid, hexanoic acid, octanoic acid, and decanoic acid (C₁₀) were from Fluka Analytical (Buchs, Switzerland); and HOAt and HATU were from GLS Biochem (Shanghai, China). DTT, Fmoc-D-Arg(Pbf)-OH, Fmoc-D-Ile-OH, Fmoc-D-Lys(Boc)-OH, Fmoc-D-Lys(Mtt)-OH, Fmoc-D-Phe-OH, Fmoc-D-Tyr(tBu)-OH, piperidine, and TentaGel^® S RAM (loading 0.24 mmol/g) were from Iris Biotech GmbH (Marktredwitz, Germany). Bromoacetic acid (BrAcOH), lauric acid (C₁₂), myristic acid (C₁₄), DIC, DIEA, DMSO, Fmoc-D-Asn(Trt)-OH, and TIS were from Sigma-Aldrich (St. Louis, MO, USA). ACN, DCM, diethyl ether, DMF, ethanol, and methanol were from VWR International (Radnor, PA, USA).

Andersen I.K., Thomsen T.T., Rashid J., Bobak T.R., Oddo A., Franzyk H., Løbner-Olesen A, & Hansen P.R. (2022). C-Locked Analogs of the Antimicrobial Peptide BP214. Antibiotics, 11(8), 1080.

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Synthesis of Triazolyl-Containing MT-II Analogues

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The ω-alkynyl-alcohols
were purchased from Alfa Aesar; Fmoc-l-Trp-(Boc)-OH, Fmoc-d-Phe-OH, and Fmoc-l-Pra-OH amino acids, Fmoc-Rink
amide resin, and HOBt were purchased from Iris Biotech GmbH (Marktredwitz,
Germany); Fmoc-l-Arg(Pbf)-OH and Fmoc-l-His(Trt)-OH
amino acids were purchased from CBL (Patras, Greece); Fmoc-l-Nle was purchased from NeoMPS (Strasbourg, France); TBTU from Advanced
Biotech Italy (Milan, Italy). Peptide-synthesis grade N,N-dimethylformamide (DMF) was purchased from Scharlau
(Barcelona, Spain); acetonitrile from Carlo Erba (Milan, Italy); dichloromethane
(DCM), trifluoroacetic acid (TFA), piperidine, acetic anhydride (Ac₂O), and N-methyl morpholine (NMM) were purchased
from Sigma-Aldrich (Milan, Italy). The scavengers for cleavage of
peptides from resin, 1,2-ethanedithiol (EDT), thioanisole, and phenol
(PhOH), were purchased from Acros Organics (Geel, Belgium), Jansenn
Chimica (Beerse, Belgium), and Carlo Erba (Milan, Italy).
The
purity of the final linear precursors (I′–X′)
and the [1,2,3]triazolyl-containing MT-II analogues (I–X) was
established by analytical RP-HPLC and exceeded 95%, their structural
integrity was established by ESI-MS.

Testa C., Scrima M., Grimaldi M., D’Ursi A.M., Dirain M.L., Lubin-Germain N., Singh A., Haskell-Luevano C., Chorev M., Rovero P, & Papini A.M. (2014). 1,4-Disubstituted-[1,2,3]triazolyl-Containing Analogues of MT-II: Design, Synthesis, Conformational Analysis, and Biological Activity. Journal of Medicinal Chemistry, 57(22), 9424-9434.

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