Rink amide resin

Manufactured by GL Biochem

Sourced in China

Rink amide resin is a solid-phase synthesis resin used in the production of peptides. It serves as a support material for the chemical reactions involved in peptide synthesis.

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Rink amide MBHA resin (10 citations) Rink amide AM resin (7 citations) Rink amide 4-methylbenzhydrylamine resin (2 citations)

8 protocols using rink amide resin

Fmoc-Protected Amino Acid Synthesis

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N_α-Fmoc-protected amino acids, HBTU, and HOBt were purchased from Inbios (Naples, Italy). Rink amide resin was purchased from GL Biochem (Shanghai, China).
99.9% ²H₂O were obtained from Aldrich (Milwaukee, USA), 98% DPC-d₃₈ was obtained from Cambridge Isotope Laboratories, Inc. (Andover, USA), and [(2,2,3,3-tetradeuterio-3-(trimethylsilanyl)]-propionic acid (TSP) was obtained from MSD Isotopes (Montreal, Canada).

Carotenuto A., Merlino F., Cai M., Brancaccio D., Yousif A.M., Novellino E., Hruby V.J, & Grieco P. (2015). Discovery of Novel Potent and Selective Agonists at the Melanocortin-3 Receptor. Journal of medicinal chemistry, 58(24), 9773-9778.

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Solid-Phase Peptide Synthesis Workflow

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N^α-Fmoc-protected amino acids,
rink amide resin (0.36 mmol/g), and O-(1H-6-chlorobenzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate
were purchased from GL Biochem (China). Fmoc-Thr(tBu)-preloaded TentaGel resin (0.18 mmol/g) was purchased from Rapp
Polymere GmbH (Germany). N,N-Dimethylformamide
(DMF), piperidine (PPD), trifluoroacetic acid (TFA), acetonitrile
(MeCN), methanol, dichloromethane (DCM), and diethyl ether (Et₂O) were purchased from Merck (Australia). N,N-Diisopropylethylamine (DIEA), trifluoromethanesulfonic
acid (TFMSA), 2,2′-(ethylenedioxy)diethanethiol, triisopropylsilane,
anisole, 2,2′-dipyridyl disulfide, 2,4,6-trimethylpyridine,
1-(2-aminoethyl)maleimide hydrochloride, and palmitic acid N-hydroxysuccinimide were purchased from Sigma-Aldrich (Australia).
All solvents were of analytical grade.

Liu M., Li Q., Delaine C., Wu H., Arsenakis Y., White B.F., Forbes B.E., Chandrashekar C, & Hossain M.A. (2023). Total Chemical Synthesis of Palmitoyl-Conjugated Insulin. ACS Omega, 8(15), 13715-13720.

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Pyropheophorbide-a Peptide Conjugation

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Fifty milligrams of GPLGFR(pbf)VGK(boc) on solid
support Rink amide resin with N-terminus fluorenylmethyloxycarbonyl
(Fmoc) modification was purchased from GL Biochem (Shanghai) Ltd.
To remove the Fmoc protecting group the peptide resin was incubated
with 20% piperidine solution in dimethylforamide (DMF). After complete
Fmoc removal, which was confirmed and quantified by UV–vis
measurements of the reaction solution (ε_300 nm= 7.87 × 10³ M^–1 cm^–1), the resin was washed with DMF. Pyropheophorbide-a acid (pyro) was added to the deprotected peptide to couple with
the N-terminal glycine in the presence of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HBTU)
and N,N-diisopropylethylamine (DIPEA)
(pyro/HBTU/peptide = 2:2:1; DIPEA = 2.5%). The reaction was mixed
under argon overnight. The resulting product was washed with DMF and
methanol (MeOH) and dried using a vacuum centrifuge.

Walsh C., Rajora M.A., Ding L., Nakamura S., Endisha H., Rockel J., Chen J., Kapoor M, & Zheng G. (2023). Protease-Activatable Porphyrin Molecular Beacon for Osteoarthritis Management. Chemical & Biomedical Imaging, 1(1), 66-80.

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Fmoc-based Peptide Synthesis and Doxorubicin Delivery

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9-Fluorenylmethyl (Fmoc)-amino acids and Rink Amide resin (100-200 mesh, substitution factor: 0.486 mM) were obtained from GL Biochem (Shanghai, China). Doxorubicin hydrochloride (DOX, >95%) was obtained from Aladdin (Shanghai, China). All other chemicals and reagents were of analytical or HPLC grade. The SMMC-7721 human hepatoma and H22 hepatoma cell lines were purchased from the National Infrastructure of Cell Line Resource. ICR mice were purchased from the Experimental Animal Center at Nanjing University of Chinese Medicine, China.

Xu L., Wang Y., Zhu C., Ren S., Shao Y., Wu L., Li W., Jia X., Hu R., Chen R, & Chen Z. (2020). Morphological transformation enhances Tumor Retention by Regulating the Self-assembly of Doxorubicin-peptide Conjugates. Theranostics, 10(18), 8162-8178.

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Peptide Synthesis with Rink Amide Resin

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The rink amide resin and all the Fmoc-protected natural amino acids for peptide synthesis were supplied by GL Biochem (Shanghai, China). Fmoc-Hexacid-OH was purchased from Hanghong (China). Other chemicals (including those mentioned in the later sections) were purchased from Sigma-Aldrich unless otherwise specified.

Ni R., Liu J, & Chau Y. (2018). Ultrasound-facilitated assembly and disassembly of a pH-sensitive self-assembly peptide. RSC Advances, 8(51), 29482-29487.

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Automated Peptide Synthesis and Purification

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All peptides used in this study were synthesized on a Liberty Blue (CEM) automated microwave solid-phase synthesizer with Rink-amide resin (GL Biochem), using Fmoc/tBu chemistry. In the synthesis, five equivalents of the amino acid were used for each coupling cycle with PyBOP activation. A double-coupling protocol was performed if needed. All peptides were cleaved in 95% TFA/2.5% H2O/2.5% TIS cleavage solution and purified by prep-RP-HPLC.

Liew H.T., To J., Zhang X., Hemu X., Chan N.Y., Serra A., Sze S.K., Liu C.F, & Tam J.P. (2021). The legumain McPAL1 from Momordica cochinchinensis is a highly stable Asx-specific splicing enzyme. The Journal of Biological Chemistry, 297(6), 101325.

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Peptide Synthesis Using Diverse Amino Acids

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N^α-Fmoc-protected amino acids, Fmoc-Phe, Fmoc-Val, Fmoc-Pro and Fmoc-DPro, Fmoc-Trp(Boc) and Fmoc-DTrp(Boc), Fmoc-Ser(tBu), Fmoc-Lys(Boc) and Fmoc-DLys(Boc), Fmoc-Leu and Fmoc-DLeu, Fmoc-Gly, Fmoc-Arg(Pbf), Fmoc-Nle and Fmoc-DNle, all were purchased from GL Biochem Ltd. (Shanghai, China). Other unconventional N^α-Fmoc-amino acids, namely Fmoc-Hyp(tBu) and Fmoc-DHyp(tBu), were purchased from Sigma-Aldrich (St. Louis, MO, USA), and Fmoc-Aic was acquired by Chem-Impex International (Wood Dale, IL, USA). Undecanoic, Tridecanoic, Pentadecanoic and Palmitic acids were purchased from Sigma-Aldrich. Cholesterol-PEG4 was obtained by following the synthetic procedures elsewhere reported [66 (link)]. Coupling reagents such as N,N,N′,N′-tetramethyl-O-(1H-benzo-triazol-1-yl)uronium hexafluorophosphate (HBTU) and 1-hydroxybenzotriazole (HOBt), as well as the Rink amide resin used, all were commercially obtained by GL Biochem Ltd. (Shanghai, China). N,N-diisopropylethylamine (DIEA), piperidine, and tri-fluoroacetic acid (TFA) were purchased from Iris-Biotech GMBH. Peptide synthesis solvents and reagents, such as N,N-dimethylformamide (DMF), dichloromethane (DCM), diethyl ether (Et2O), water and acetonitrile (MeCN) for HPLC, were reagent grade acquired from commercial sources (Sigma-Aldrich and VWR) and used without further purification.

Zannella C., Chianese A., Palomba L., Marcocci M.E., Bellavita R., Merlino F., Grieco P., Folliero V., De Filippis A., Mangoni M., Nencioni L., Franci G, & Galdiero M. (2022). Broad-Spectrum Antiviral Activity of the Amphibian Antimicrobial Peptide Temporin L and Its Analogs. International Journal of Molecular Sciences, 23(4), 2060.

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Synthesis and Characterization of Labeled Arginine Peptide

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MRSA USA300 (ATCC-BAA-1680) was purchased from ATCC (USA). Nαfluorenylmethyloxy carbonyl-Nω-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-L-arginine, Nα-fluorenylmethyloxy carbonyl-4-phenyl-L-phenylalanine and Rink amide resin (loading factor 0.6 mmol/g) were purchased from GL Biochem (China). CD3OD and labelled amino acids were purchased from Chembridge Isotopes Laboratories, USA. 5-carboxyfluorescein, GdCl3, ethylenediaminetetraacetic acid (EDTA), Triton-X and all solvents reported herein were purchased from Sigma-Aldrich, USA. Cation- Phospholipids were purchased from Avanti Polar Lipids, USA. Deuterated phospholipids were purchased from Anatrace, USA.

Lau Q.Y., Li J., Sani M.A., Sinha S., Li Y., Ng F.M., Kang C., Bhattacharjya S., Separovic F., Verma C, & Chia C.S.B. (2018). Elucidating the bactericidal mechanism of action of the linear antimicrobial tetrapeptide BRBR-NH₂. Biochimica et biophysica acta. Biomembranes, 1860(8).

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