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N2 - The peptide nucleic acid backbone Fmoc-AEG-OBn has been synthesized via a scalable and cost-effective route. Ethylenediamine is mono-Boc protected, then alkylated with benzyl bromoacetate. The Boc group is removed and replaced with an Fmoc group. The synthesis was performed starting with 50 g of Boc anhydride to give 31 g of product in 32 overall yield. The Fmoc-protected PNA backbone is a key intermediate in the synthesis of nucleobase-modified PNA monomers. Thus, improved access to this molecule is anticipated to facilitate future investigations into the chemical properties and applications of nucleobase-modified PNA.

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Dde-protected PNA monomers, orthogonal to Fmoc, for the synthesis of PNA ..

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AB - The peptide nucleic acid backbone Fmoc-AEG-OBn has been synthesized via a scalable and cost-effective route. Ethylenediamine is mono-Boc protected, then alkylated with benzyl bromoacetate. The Boc group is removed and replaced with an Fmoc group. The synthesis was performed starting with 50 g of Boc anhydride to give 31 g of product in 32 overall yield. The Fmoc-protected PNA backbone is a key intermediate in the synthesis of nucleobase-modified PNA monomers. Thus, improved access to this molecule is anticipated to facilitate future investigations into the chemical properties and applications of nucleobase-modified PNA.

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This protocol describes the gram-scale solution-phase synthesis of the colorimetric caspase-3/7 substrate Ac-DEVD-pNA. The caspase enzymes are integral to cellular inflammation and apoptotic cascades, and are commonly studied by cell biologists, medicinal chemists and chemical biologists. In particular, the assessment of caspase enzymatic activity is a standard method to evaluate cell death pathways and new apoptosis-modulating agents. Caspase enzymatic activity can be conveniently monitored with peptidic chromogenic or fluorogenic substrates, with certain peptide sequences imparting selectivity for certain caspases. The synthesis of these peptide substrates is typically carried out by solid-phase synthesis, a method that is not ideal for production of the gram quantities needed for high-throughput screening. Described herein is a facile method for the synthesis of the Ac-DEVD-pNA caspase-3/7 substrate using solution-phase peptide synthesis. This protocol, involving iterative PyBOP-mediated couplings and Fmoc deprotections, is rapid (about 5 d), operationally simple and can be used to generate over 1 g of product at a fraction of the cost of the commercial substrate.

Dde-protected PNA monomers, orthogonal to Fmoc, for the synthesis of PNA–peptide conjugates
Here we report the synthesis of new PNA monomers for pseudocomplementary PNA (pcPNA) that are fully compatible with standard Fmoc chemistry. The …

Synthesis of PNA-Peptide Conjugates | SpringerLink

In the next step, the synthesis of the PNA backbone monomer using the fluorenylmethoxycarbonyl (Fmoc) protection occurred as described by Atherton and Sheppard.[]

21/06/2017 · Solid phase synthesis of DNA-3'-PNA chimeras by using Bhoc/Fmoc PNA monomers

Fmoc/Acyl protecting groups in the synthesis of …

AB - This protocol describes the gram-scale solution-phase synthesis of the colorimetric caspase-3/7 substrate Ac-DEVD-pNA. The caspase enzymes are integral to cellular inflammation and apoptotic cascades, and are commonly studied by cell biologists, medicinal chemists and chemical biologists. In particular, the assessment of caspase enzymatic activity is a standard method to evaluate cell death pathways and new apoptosis-modulating agents. Caspase enzymatic activity can be conveniently monitored with peptidic chromogenic or fluorogenic substrates, with certain peptide sequences imparting selectivity for certain caspases. The synthesis of these peptide substrates is typically carried out by solid-phase synthesis, a method that is not ideal for production of the gram quantities needed for high-throughput screening. Described herein is a facile method for the synthesis of the Ac-DEVD-pNA caspase-3/7 substrate using solution-phase peptide synthesis. This protocol, involving iterative PyBOP-mediated couplings and Fmoc deprotections, is rapid (about 5 d), operationally simple and can be used to generate over 1 g of product at a fraction of the cost of the commercial substrate.

Fmoc Solid Phase Synthesis of Polyamides Containing Pyrrole and ..

(Scheme 6) exemplifies a commonly applicable instruction for synthesis of molecules suitable for functionalization of PNA: Fmoc-C2-glycine-tert-butyl ester 9 reacts with the carbonic acid chloride of the DAR component X 14 to the corresponding tert-butyl ester of the peptide nucleic acid monomer (Fmoc protected) 15. After hydrolysis of the tert-butyl ester catalyzed by acid, the peptide nucleic acid monomer (Fmoc protected) functionalized with the DAR component X 16 is received.