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Fmoc-D-Arg(Pbf)-Alko-PEG Resin

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Wang resins are the standard supports for the preparation of peptide acids by the Fmoc batch solid phase synthesis strategy. Fmoc amino acids are pre-loaded to Wang resins so that that epimerization and dipeptide formation are minimized.

Category

Wang Resin with Amino Acids

Catalog number

BAT-001148

Synonyms

Fmoc-D-Arg(Pbf)-Wang-PEG Resin; N-α-(9-Fluorenylmethoxycarbonyl)-N-ω-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-D-arginine p-methoxybenzyl alcohol polyethyleneglycol resin

DVB Crosslinking

1% DVB

Substitution

1.0-1.4 meq/g

Storage

Store at 2-8 °C

Fmoc-D-Arg(Pbf)-Alko-PEG Resin, a specialized chemical reagent crucial in peptide synthesis, finds diverse applications across the realm of chemical research. Here are the key applications presented with high perplexity and burstiness:

Peptide Synthesis: Serving as a cornerstone in solid-phase peptide synthesis, Fmoc-D-Arg(Pbf)-Alko-PEG Resin enables the intricate assembly of complex peptide structures. This resin facilitates the iterative addition of amino acids while safeguarding side chains, ensuring the precise formation of peptides vital for advancements in pharmaceutical research and drug development. The methodical nature of this approach underpins the creation of tailored peptide sequences with unparalleled precision.

Drug Delivery Studies: Delving into the realms of advanced drug delivery systems, researchers harness the power of this resin to craft peptide-based conjugates with enhanced characteristics. By integrating the resin into peptide synthesis, scientists can engineer drug conjugates that enhance solubility, stability, and targeting of therapeutic molecules. This sophisticated approach elevates the efficacy and safety of peptide-based drugs, heralding a new era in drug delivery innovation.

Bioconjugation Research: Stepping into the arena of bioconjugation studies, Fmoc-D-Arg(Pbf)-Alko-PEG Resin emerges as a key player in linking peptides to diverse biomolecules and surfaces for multifaceted applications. The resin empowers precise control over the length and composition of peptide linkers, facilitating the creation of functionalized biomaterials with tailored properties. These bioconjugates find utility across diagnostics, imaging, and therapeutic realms, showcasing the versatility and utility of this resin.

Protein-Protein Interaction Studies: Unlocking the mysteries of protein-protein interactions, this resin aids in synthesizing peptides essential for probing the intricate dance of cellular processes. By fabricating peptides that mimic specific protein interaction sites, researchers can delve into binding affinities and mechanistic insights crucial for drug discovery and intervention strategies. This profound understanding of protein interactions shapes the landscape of therapeutic development and drives forward innovative solutions for complex biological challenges.

1. Perfluoro-tert-butanol for selective on-resin detritylation: a mild alternative to traditionally used methods

Anita Wester, Anna Mette Hansen, Paul R Hansen, Henrik Franzyk Amino Acids. 2021 Sep;53(9):1455-1466. doi: 10.1007/s00726-021-03059-8. Epub 2021 Aug 19.

Solid-phase synthesis of cyclic, branched or side-chain-modified peptides typically involves introduction of a residue carrying a temporary side-chain protecting group that undergoes selective on-resin removal. In particular, Nα-Fmoc-Nε-(4-methyltriphenylmethyl) (Mtt)-protected lysine and its shorter analogues are commercially available and extensively used in this context. Nevertheless, rapid reliable methods for on-resin removal of Mtt groups in the presence of tert-butyloxycarbonyl (Boc) groups are needed. Current commonly used conditions involve low concentrations (1-3%) of trifluoroacetic acid (TFA) in dichloromethane, albeit adjustment to each specific application is required to avoid premature removal of Boc groups or cleavage from the linker. Hence, a head-to-head comparison of several deprotection conditions was performed. The selected acids represent a wide range of acidity from TFA to trifluoroethanol. Also, on-resin removal of the N-(4-methoxytriphenylmethyl) (Mmt) and O-trityl groups (on serine) was investigated under similar conditions. The mildest conditions identified for Mtt deprotection involve successive treatments with 30% hexafluoroisopropanol (HFIP) or 30% perfluoro-tert-butanol [(CF3)3COH] in dichloromethane (3 × 5 or 3 × 15 min, respectively), while 30% HFIP, 30% (CF3)3COH, or 10% AcOH-20% trifluoroethanol (TFE) in CH2Cl2 (3 × 5 min) as well as 5% trichloroacetic acid in CH2Cl2 (3 × 2 min) enabled Mmt removal. Treatment with 1% TFA with/without 2% triisopropylsilane added (3 × 5 min), but also prolonged treatment with 30% (CF3)3COH (5 × 15 min), led to selective deprotection of an O-Trt group on a serine residue. In all cases, the sequences also contained N-Boc or O-tBu protecting groups, which were not affected by 30% HFIP or 30% (CF3)3COH even after a prolonged reaction time of 4 h. Finally, the optimized conditions involving HFIP or (CF3)3COH proved applicable also for selective deprotection of a longer resin-bound peptide [i.e., Ac-Gly-Leu-Leu-Lys(Mtt)-Arg(Pbf)-Ile-Lys(Boc)-Ser(tBu)-Leu-Leu-RAM-PS] as well as allowed for an almost complete deprotection of a Dab(Mtt) residue.

2. Efficient synthesis of CN2097 using in situ activation of sulfhydryl group

Shaban Darwish, Keykavous Parang, John Marshall, Dennis J Goebel, Rakesh Tiwari Tetrahedron Lett. 2017 Aug 2;58(31):3053-3056. doi: 10.1016/j.tetlet.2017.06.066. Epub 2017 Jun 23.

CN2097 (R7Cs-sCYK[KTE(β-Ala)]V) is a rationally designed peptidomimetic that shows effectiveness in preclinical models for the treatment of neurological disorders, such as Angelman syndrome, traumatic brain injury (TBI) and stroke. Because of its therapeutic activity for the treatment of human CNS disorders, there was an urgent need to develop an efficient strategy for large-scale synthesis of CN2097. The synthesis of CN2097 was accomplished using Fmoc/tBu solid phase chemistry in multiple steps. Two different peptide fragments (activated polyarginine peptide Npys-sCR7 and CYK[KTE(β-Ala)]V) were synthesized, followed by solution phase coupling in water. Activation of the polyarginine (CR7) was achieved in situ during cleavage of protected peptide (C(Trt)R(Pbf)7) from the Rink amide resin using 5 equiv. of 2,2-dithopyridine in TFA:TIS:H2O (95:2.5:2.5, v/v/v) for 4 h. The disulfide coupling was efficient which provided a 60% yield.

3. Global analysis of peptide cyclization efficiency

Amit Thakkar, Thi Ba Trinh, Dehua Pei ACS Comb Sci. 2013 Feb 11;15(2):120-9. doi: 10.1021/co300136j. Epub 2013 Jan 7.

Cyclic peptides are of considerable interest in drug discovery and nanotechnology. However, macrocyclization of peptides and other compounds has often been perceived as synthetically challenging and the cyclization yields are affected by several factors including the ring size, peptide sequence, and the reaction conditions. Through the screening of combinatorial peptide libraries, we analyzed the cyclization efficiency of >2 million peptide sequences to determine the effect of ring size, peptide sequence, and solvent on the backbone (N-to-C) cyclization of peptides. Our results show that on-resin cyclization of medium- and large-sized rings (cyclohexapeptides and above) with PyBOP is essentially quantitative for ≥ 99.96% of the sequences, with small amounts of dimer formation observed for <4% of these sequences. Cyclization of small rings (cyclotetrapeptides and cyclopentapeptides) is considerably more difficult and accompanied by significant cyclic dimer formation. Peptides that are difficult to cyclize are generally rich in Lys(Boc) and Arg(Pbf) residues as well as sterically hindered residues [e.g., Thr(tBu)] at the N-terminus. The majority of these difficult sequences can be cyclized to completion by the addition of aqueous additives to the cyclization reaction.