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KW - Solid-phase peptide synthesis

The head-to-tail on-resin cyclization strategy is an important tool in solid phase peptide synthesis that takes advantage of the resin-induced pseudo-dilution effects, thereby limiting undesirable dimerization.

Synthesis of Peptide-Based Polymers by Microwave-Assisted Cycloaddition Backbone Polymerization.

Fast and precise heating by microwave irradiation during solid-phase peptide synthesis (SPPS) can reduce reaction times as well as provide better purities and greater yields for the synthesis of difficult peptides. Microwave- assisted SPPS has proven to be a useful and reliable tool for the synthesis of peptides as well as small proteins. It is particularly well suited for sequences with a high propensity to form β-sheet-type structures and for sterically difficult couplings. In this protocol, conditions and detailed procedures are described for performing microwave-assisted SPPS using the Syro Wave™. Here we describe the synthesis of two difficult peptide sequences: the first is derived from the C-terminus of the MuLV CTL epitope, the second is a de novo designed peptide with a C-terminal alkyne.

Advances in Solid-Phase Cycloadditions for Heterocyclic Synthesis.

M., Solid-phase synthesis of C-terminally modified peptides.

AB - Various asymmetrically substituted phthalocyanines (Pcs) and porphyrazines (Pzs) have been synthesized in good yields using a solid-phase synthesis method with a poly(ethylene glycol) (PEG) resin attached to an indole linker as the solid support. These compounds are formed by cross condensation of maleonitrile or phthalonitrile with another phthalonitrile covalently bonded to the solid support with an amino linking group. The polymer bound Pc or Pz is separated by filtration, and washing the symmetrical Pc or Pz by-product. The amine Pc-appended to polyethylene glycol resin is further reacted to yield azide whilst still on the solid support. Cleavage of the Pc or Pz off the solid support results in 3:1 asymmetric Pz or Pz with high degree of purity, requiring minimal further purification. The use of hydrophilic PEG-based resin allows the symmetrical compound to be removed completely by washing whereas the acid labile indole linker makes it easier to cleave the product under mild conditions. The conjugation abilities of these compounds have been demonstrated by the successful conjugation of one of the azide Pcs with a peptide elaborated with an alkyne function. Use of microwave for the synthesis of these compounds results in shorter reaction times, higher yields and higher degree of purity.

N2 - Various asymmetrically substituted phthalocyanines (Pcs) and porphyrazines (Pzs) have been synthesized in good yields using a solid-phase synthesis method with a poly(ethylene glycol) (PEG) resin attached to an indole linker as the solid support. These compounds are formed by cross condensation of maleonitrile or phthalonitrile with another phthalonitrile covalently bonded to the solid support with an amino linking group. The polymer bound Pc or Pz is separated by filtration, and washing the symmetrical Pc or Pz by-product. The amine Pc-appended to polyethylene glycol resin is further reacted to yield azide whilst still on the solid support. Cleavage of the Pc or Pz off the solid support results in 3:1 asymmetric Pz or Pz with high degree of purity, requiring minimal further purification. The use of hydrophilic PEG-based resin allows the symmetrical compound to be removed completely by washing whereas the acid labile indole linker makes it easier to cleave the product under mild conditions. The conjugation abilities of these compounds have been demonstrated by the successful conjugation of one of the azide Pcs with a peptide elaborated with an alkyne function. Use of microwave for the synthesis of these compounds results in shorter reaction times, higher yields and higher degree of purity.

Microwave-Assisted Peptide Synthesis

Mit der Liberty-Technologie sind wir das erste Mal in der Lage, Mikrowellenenergie für den vollständigen Prozess der Peptidesynthese einzusetzen.

Various asymmetrically substituted phthalocyanines (Pcs) and porphyrazines (Pzs) have been synthesized in good yields using a solid-phase synthesis method with a poly(ethylene glycol) (PEG) resin attached to an indole linker as the solid support. These compounds are formed by cross condensation of maleonitrile or phthalonitrile with another phthalonitrile covalently bonded to the solid support with an amino linking group. The polymer bound Pc or Pz is separated by filtration, and washing the symmetrical Pc or Pz by-product. The amine Pc-appended to polyethylene glycol resin is further reacted to yield azide whilst still on the solid support. Cleavage of the Pc or Pz off the solid support results in 3:1 asymmetric Pz or Pz with high degree of purity, requiring minimal further purification. The use of hydrophilic PEG-based resin allows the symmetrical compound to be removed completely by washing whereas the acid labile indole linker makes it easier to cleave the product under mild conditions. The conjugation abilities of these compounds have been demonstrated by the successful conjugation of one of the azide Pcs with a peptide elaborated with an alkyne function. Use of microwave for the synthesis of these compounds results in shorter reaction times, higher yields and higher degree of purity.

AB - A novel microwave-assisted solid-phase peptide synthesis utilizing N-Fmoc-protected(α-aminoacyl)benzotriazoles was applied in the preparation of tri-, tetra-, penta-, hexa-, and heptapeptides in 71% average crude yield.

S., Revisiting nucleophilic substitution reactions: microwave-assisted synthesis of azides, thiocyanates, and sulfones in an aqueous medium.
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Microwave-assisted Solid Phase Peptide Synthesis on …

It was not long after this seminal work that peptide chemists were using microwave technology to improve the solid-phase synthesis of more complex biomolecules.

Microwave-assisted solid-phase peptide synthesis of …

The peptide backbone (Gly-Val-Tyr-Leu-His-Ile-Glu) was synthesized on Fmoc-Glu(Wang resin)-ODmab with the side chain γ-carboxyl group anchored to the resin and the α-carboxyl protected by the Dmab orthogonal protecting group in 91% crude purity.

applied to accelerate the reactions in solid phase peptide synthesis

N2 - A novel microwave-assisted solid-phase peptide synthesis utilizing N-Fmoc-protected(α-aminoacyl)benzotriazoles was applied in the preparation of tri-, tetra-, penta-, hexa-, and heptapeptides in 71% average crude yield.

Microwave-Assisted Peptide Synthesis - Chemtour

Preparation, Characterization, and Application of Poly(vinyl alcohol)-graft-Poly(ethylene glycol) Resins: Novel Polymer Matrices for Solid-Phase Synthesis.

Microwave-Assisted Peptide Synthesis: ..

Synthesis of Enantiomerically Pure α-[4-(1-Substituted)-1,2,3-triazol-4-yl]-benzylacetamides via Microwave-Assisted Click Chemistry: Towards New Potential Antimicrobial Agents.

Microwave-assisted solid-phase peptide ..

A novel microwave-assisted solid-phase peptide synthesis utilizing N-Fmoc-protected(α-aminoacyl)benzotriazoles was applied in the preparation of tri-, tetra-, penta-, hexa-, and heptapeptides in 71% average crude yield.

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