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Fmoc amino acids

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Fmoc-amino acids are a class of amino acid derivatives commonly used in solid-phase peptide synthesis. They serve as building blocks for the construction of peptide and protein molecules. Fmoc-amino acids provide a protected amino group, enabling controlled peptide chain assembly. The Fmoc (fluorenylmethyloxycarbonyl) group serves to temporarily block the amino terminus, facilitating stepwise addition of amino acids during the synthesis process.

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Lab products found in correlation

Triisopropylsilane, by Merck Group (3 mentions) Rink amide resin, by Merck Group (3 mentions) Zncl2, by Fujifilm (2 mentions) Tris hydroxymethyl aminomethane tris, by Nacalai Tesque (2 mentions) Fmoc rink amide mbha resin, by Merck Group (2 mentions) Piperidine, by Merck Group (2 mentions) Methanol, by Thermo Fisher Scientific (2 mentions) Triisopropylsilane, by Tokyo Chemical Industry (1 mentions) Milli q integral 3 system, by Merck Group (1 mentions) Piperazine, by Merck Group (1 mentions) O 7 azabenzotriazol 1 yl n n n n tetramethyluronium hexafluorophosphate hatu, by Merck Group (1 mentions) N dimethylformamide dmf, by Merck Group (1 mentions) 6410 agilent lc ms triple quadrupole mass spectrometer, by Agilent Technologies (1 mentions) Acetonitrile mecn, by Merck Group (1 mentions) Dichloromethane, by Merck Group (1 mentions) Trifluoroacetic acid, by Merck Group (1 mentions) Ch3cn, by Merck Group (1 mentions) Ch2cl2, by Merck Group (1 mentions) Ascorbic acid, by Merck Group (1 mentions) N n dimethylformamide (dmf), by Merck Group (1 mentions)

13 protocols using fmoc amino acids

1

Fmoc-Strategy Peptide Synthesis

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Peptide synthesis was carried out using a conventional Fmoc-strategy with Fmoc-amino acids (Merck Ltd. Darmstadt, Germany) and Fmoc-NH-SAL-MBHA resin (100–200 mesh, Watanabe Chemical Industries Ltd. Hiroshima, Japan). Other reagents used for peptide synthesis, namely, N,N-diisopropylethylamine and trifluoroacetic acid, were purchased from Watanabe Chemical Industries Ltd., and 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate and 1-hydroxybenzotriazole were purchased from Kokusan Chemical Co., Ltd. (Tokyo, Japan). Triisopropylsilane and xylenol orange (XO) were purchased from Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan). Hydrochloric acid (HCl), 1,2-ethanedithiol, CdCl2⋅2H2O, and tris(hydroxymethyl)aminomethane (Tris) were purchased from Nacalai Tesque Co. Ltd. (Kyoto, Japan). ZnCl2 was purchased from FUJIFILM Wako Pure Chemical Corporation (Osaka, Japan). Water for the experiments was purified using a Milli-Q Integral 3 system (Merck Millipore, Darmstadt, Germany). Other solvents and reagents were obtained from commercial suppliers and used without further purification.
Sumiyoshi S., Suyama K., Tanaka N., Andoh T., Nagata A., Tomohara K., Taniguchi S., Maeda I, & Nose T. (2022). Development of truncated elastin-like peptide analogues with improved temperature-response and self-assembling properties. Scientific Reports, 12, 19414.
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2

Solid-Phase Peptide Synthesis Protocol

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Trifluoroacetic acid (TFA), Triisopropylsilane (TIS), Fmoc amino acids and coupling reagent O-(7-Azabenzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (HATU) and benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (PyBop) were supplied by the Merck Co, Germany. Solvents, acetonitrile (MeCN), Piperazine, N, N-diisopropylethylamine (DIPEA), diethylether, Dichloromethane (DCM), N, N-dimethylformamide (DMF), and methanol (MeOH) were purchased from the Merck Co, Germany. 2-Chlorotritylchloride(2-CTC) resin (1% DVB, 200-400 mesh, 1 mmol/g) was from the Santa Cruz Biotechnology Co, USA. Commercially available chemicals were used as received unless otherwise stated. Fourier Transform Infrared spectra were obtained by the Shimadzu recording spectrometer, Japan. The mass spectral measurements were performed using a 6410 Agilent LCMS triple quadrupole mass spectrometer (LCMS) with an electrospray ionization (ESI) interface, USA. The cell lines were purchased from Iranian Biological Resource Center (IBRC), Tehran, Iran.
Tehrani M.H., Bamoniri A, & Gholibeikian M. (2018). The toxicity study of synthesized inverse carnosine peptide analogues on HepG2 and HT-29 cells. Iranian Journal of Basic Medical Sciences, 21(1), 39-46.
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3

Solid-Phase Peptide Synthesis Protocols

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All
reagents and solvents were obtained from
commercial suppliers and used without further purification. Fmoc-Rink-MBHA-Polystyrene
and Fmoc-Rink-ChemMatrix resins were prepared by reaction of Fmoc-Rink-OH
linker with commercial MBHA-Polystyrene or ChemMatrix resins following
controlled acetylation after 0.53 or 0.43 mmol/g substitution, respectively.
All the Fmoc-amino acids, DIEA, I2, ascorbic acid, Ac2O, and resins were purchased from Merck. Organic solvents
(analytical grade) (DMF, CH2Cl2, MeOH, Et2O, and CH3CN) were purchased from Merck. RP-HPLC
quality acetonitrile (CH3CN) and ultrapure water quality
were used for RP-HPLC analysis and purification.
Vicente F.E., González-Garcia M., Diaz Pico E., Moreno-Castillo E., Garay H.E., Rosi P.E., Jimenez A.M., Campos-Delgado J.A., Rivera D.G., Chinea G., Pietro R.C., Stenger S., Spellerberg B., Kubiczek D., Bodenberger N., Dietz S., Rosenau F., Paixão M.W., Ständker L, & Otero-González A.J. (2019). Design of a Helical-Stabilized, Cyclic, and Nontoxic Analogue of the Peptide Cm-p5 with Improved Antifungal Activity. ACS Omega, 4(21), 19081-19095.
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4

Lipid-based Nanoparticle Synthesis

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Fmoc-amino acids and Rink Amide AM resin were obtained from Merck (Darmstadt, Germany). NBD-DOPE, rhodamine-DOPE, and 1,2-distearoyl-sn-glycero-3-phosphocholine (DSPC) were obtained from Avanti Polar Lipids (Alabaster, AL). 1,2-Distearoyl-sn-glycero-3-phosphoethanolamine- N-[methoxy (polyethylene glycol)-2000] (mPEG2000-DSPE) and DLin-MC3-DMA were purchased from NOF (Tokyo, Japan) and MedChemExpress (Monmouth Junction, NJ, USA), respectively. All other chemicals were reagent-grade, commercially obtained products.
Sugimoto Y., Suga T., Umino M., Yamayoshi A., Mukai H, & Kawakami S. (2023). Investigation of enhanced intracellular delivery of nanomaterials modified with novel cell-penetrating zwitterionic peptide-lipid derivatives. Drug Delivery, 30(1), 2191891.
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5

Synthesis and Purification of Peptide Derivatives

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Acetonitrile (ACN), 2-chlorotrityl chloride resin (0.8 mmol g–1, Bachem dichloromethane (DCM) (Chem-supply), hydrazine monohydrate 64–65% (Sigma-Aldrich), methanol (Scharlau), N,N′-diisopropylethylamine (DIEA) (Sigma-Aldrich), Fmoc-amino acids (Merck), l-3,5-dihydroxyphenylglycine (Dpg) (Sigma Aldrich), (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate (COMU) (Merck), formic acid (FA), triethylamine (TEA) (Sigma-Aldrich), 2,6-lutidine (Sigma-Aldrich), 1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU) (Sigma-Aldrich), N,N-dimethylformamide (DMF) (Ajax Finechem), trifluoroacetic acid (TFA) (Sigma-Aldrich), triisopropylsilane (TIS) (Sigma-Aldrich), urea (Sigma-Aldrich), NaH2PO4 (Sigma-Aldrich), NaNO2 (Sigma-Aldrich), coenzyme A (Affymetrix).
Schoppet M., Peschke M., Kirchberg A., Wiebach V., Süssmuth R.D., Stegmann E, & Cryle M.J. (2018). The biosynthetic implications of late-stage condensation domain selectivity during glycopeptide antibiotic biosynthesis †Electronic supplementary information (ESI) available. See DOI: 10.1039/c8sc03530j. Chemical Science, 10(1), 118-133.
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6

Organic Synthesis of Thiazole Derivatives

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All solvents used in this study were of analytical grade. Reagents and solvents were purchased from Novabiochem (Fmoc-amino acids and Fmoc-Rink Amide MBHA resin), Merck (TFA and other solvents), Sigma–Aldrich (coupling agents, piperidine, N-ethyl-N,N-diisopropylamine (DIEA) and all thiazole derivatives).
Duarte D, & Vale N. (2021). Synergistic Interaction of CPP2 Coupled with Thiazole Derivates Combined with Clotrimazole and Antineoplastic Drugs in Prostate and Colon Cancer Cell Lines. International Journal of Molecular Sciences, 22(21), 11984.
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7

Peptide Synthesis Reagents and Materials

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Fmoc-amino acids were purchased from Merck Ltd. (Darmstadt, Germany). Fmoc-NH-SAL-MBHA resin (100–200 mesh); N,N-diisopropylethylamine (DIPEA); and trifluoroacetic acid (TFA) were purchased from Watanabe Chemical Industries Ltd. (Hiroshima, Japan). 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate (HBTU) and 1-hydroxybenzotriazole (HOBt) were purchased from Kokusan Chemical Co., Ltd. (Tokyo, Japan). Triisopropylsilane (TIS) and xylenol orange were purchased from Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan). Hydrochloric acid (HCl); nitric acid; 1,2-ethanedithiol (EDT); CdCl2·2.5H2O; NiCl2·6H2O; MnSO4·5H2O; and tris(hydroxymethyl)aminomethane (Tris) were purchased from Nacalai Tesque Co. Ltd (Kyoto, Japan). ZnCl2 and Multielement Standard Solution W-V were purchased from FUJIFILM Wako Pure Chemical Corporation (Osaka, Japan). Water for the experiments was purified by Milli-Q Integral 3 (Merck Millipore, Darmstadt, Germany). Other solvents and reagents were obtained from commercial suppliers and used without further purification.
Sumiyoshi S., Suyama K., Tatsubo D., Tanaka N., Tomohara K., Taniguchi S., Maeda I, & Nose T. (2022). Metal ion scavenging activity of elastin-like peptide analogues containing a cadmium ion binding sequence. Scientific Reports, 12, 1861.
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8

Peptide Synthesis and Characterization

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All Fmoc amino acids and Rink Amide resin were purchased from EMD Millipore. Peptide syntheses were carried out following the standard solid phase Fmoc synthesis. Analysis and purification of the peptides was performed using the Dionex Summit high-performance liquid chromatography (HPLC) system (Dionex Corporation, Sunnyvale, CA) and reverse phase HPLC column Higins Analytical (Higins Analytical, Mountain View, CA) (C18, 4.6 mm × 250 mm). The mobile phase was 0.1% trifluoroacetic acid (TFA) in water (solvent A) and 0.1% TFA in 90 % acetonitrile (CH3CN) in water (solvent B). Matrix assisted laser desorption/ionization mass spectrometry was performed by the Canary Center proteomics facility on AB Sciex 5800 TOF/TOF System (Foster City, CA). The absorbance measurements were performed using Cary50 (Varian), fluorescence measurements using FluoroMax4 (Horiba).
Levi J., Sathirachinda A, & Gambhir S.S. (2014). A High Affinity, High Stability Photoacoustic Agent for Imaging Gastrin Releasing Peptide Receptor in Prostate Cancer. Clinical cancer research : an official journal of the American Association for Cancer Research, 20(14), 3721-3729.
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9

Synthesis and Evaluation of Thiazole-Conjugated Cell-Penetrating Peptides

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All solvents used in this study were of analytical grade. Reagents and solvents were purchased from Novabiochem (Fmoc-amino acids and Fmoc-Rink Amide MBHA resin), Merck (TFA and other solvents) and Sigma-Aldrich (coupling agents, piperidine, DIEA and thiazole Fig. 1. Structure of the main compounds synthesized in this project. All compounds were synthesized by SPPS, analysed by HPLC and LC/MS and purified by MPLC (see Materials and Methods). Synthesis was initiated with the base peptide, CPP2, whose amino acid sequence is described above. Subsequently, N-terminal modifications of this peptide were made with 6 thiazole derivatives. The first four of these conjugates have in their structure a linker (C2) between the peptide and the thiazole derivative, while the other two do not have this structure. These compounds were all studied in Caco-2 cells for their anti-tumour effect. derivatives).
Duarte D., Fraga A.G., Pedrosa J., Martel F, & Vale N. (2019). Increasing the potential of cell-penetrating peptides for cancer therapy using a new pentagonal scaffold. European journal of pharmacology, 860.
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10

Solid-Phase Peptide Synthesis

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Rink amide
resin, Fmoc-amino acids, Triton-X, piperidine, N,N-dimethylformamide (DMF), dichloromethane (DCM), dicyclohexylcarbodiimide
(DCC), 1-hydroxy-6-chloro-benzotriazole (6-Cl-HOBt), ninhydrin, potassium
cyanide (KCN), ethanol, pyridine, phenol, trifluoroacetic acid (TFA),
ethyl ether, triisopropylsilane (TIS), ethanedithiol (EDT), acetonitrile
(ACN), methanol (MeOH), and Supelco solid-phase extraction columns
were purchased from Sigma-Aldrich (St. Louis, MO). Fmoc-Dip-OH was
obtained from AAPPTec (Louisville, KY). A Zorbax Eclipse XDB-C18 column
was purchased from Agilent Technologies (California), a SunShell C18
column was purchased from ChromaNik Technologies Inc (Osaka, Japan),
and a Chromolith High Resolution RP-18e column was purchased from
Merk (New Jersey).
González-López N.M., Insuasty-Cepeda D.S., Huertas-Ortiz K.A., Reyes-Calderón J.E., Martínez-Ramírez J.A., Fierro-Medina R., Jenny Rivera-Monroy Z, & García-Castañeda J.E. (2022). Gradient Retention Factor Concept Applied to Method Development for Peptide Analysis by Means of RP-HPLC. ACS Omega, 7(49), 44817-44824.
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