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solution and solid phase peptide synthesis.

Rapid, Continuous Solution-Phase Peptide Synthesis: Application to Peptides of Pharmaceutical Interest†

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or solution-phase methods for peptide synthesis have an elegant ..

The success of solid phase peptide synthesis is often limited by the aggregation of the growing peptide chains on the resin. Working from the results of a study of model coupling reactions in solution between Z-Gly-Phe-OH and H-Phe-OBzl, we have achieved higher efficiency in the repetitive solid phase fragment condensation of VGVAPG, in a 3:1 chloroform-phenol solvent system, using diisopropylcarbodiimide (DIC) as coupling agent, and a combination of 3-hydroxy-3,4-dihydro-4-oxo-1,2,3-benzotriazine (HODhbt) and its tetrabutyl ammonium salt as additive, than in DMF with DIC and HODhbt alone.

Preparation of the caspase-3/7 substrate Ac-DEVD-pNA by solution-phase peptide synthesis

AB - The success of solid phase peptide synthesis is often limited by the aggregation of the growing peptide chains on the resin. Working from the results of a study of model coupling reactions in solution between Z-Gly-Phe-OH and H-Phe-OBzl, we have achieved higher efficiency in the repetitive solid phase fragment condensation of VGVAPG, in a 3:1 chloroform-phenol solvent system, using diisopropylcarbodiimide (DIC) as coupling agent, and a combination of 3-hydroxy-3,4-dihydro-4-oxo-1,2,3-benzotriazine (HODhbt) and its tetrabutyl ammonium salt as additive, than in DMF with DIC and HODhbt alone.

Peptide Synthesis —BIO-PROTOCOL

General Protocols and procedures utilized in solid phase peptide synthesis, ..

The Fmoc/TAEA and Bsmoc/TAEA methods for the rapid, continuous solution synthesis of peptide segments are shown to be applicable to the gram-scale synthesis of short peptides as well as, for the first time, to the synthesis of a relatively long (22-mer) segment, (hPTH 13−34). In the latter case the crude product was of significantly greater purity than a sample obtained via a solid-phase protocol. The Bsmoc methodology was optimized by a new technique involving filtration of the growing partially deprotected peptide at each coupling−deprotection cycle through a short column of silica gel.

N2 - The success of solid phase peptide synthesis is often limited by the aggregation of the growing peptide chains on the resin. Working from the results of a study of model coupling reactions in solution between Z-Gly-Phe-OH and H-Phe-OBzl, we have achieved higher efficiency in the repetitive solid phase fragment condensation of VGVAPG, in a 3:1 chloroform-phenol solvent system, using diisopropylcarbodiimide (DIC) as coupling agent, and a combination of 3-hydroxy-3,4-dihydro-4-oxo-1,2,3-benzotriazine (HODhbt) and its tetrabutyl ammonium salt as additive, than in DMF with DIC and HODhbt alone.

SpringerProtocols: Search Results

12/03/2013 · The two major chemical techniques for peptide production are SPPS and solution phase synthesis (SPS)

Preliminary solution phase studies with simple amines confirmed the ability of reagent (±)–1 to convert a primary amine to a nitrone and revealed reaction conditions consisting of aqueous DMF with a small amount of added acid as preferred conditions. We immediately turned to the more challenging and relevant application of (±)-1 for the synthesis of solid supported N-terminal peptide hydroxylamines. Using tripeptide 7 as a model substrate, we examined the utility of reagent (±)-1 to effect the formation of the N-terminal hydroxylamine. In our initial efforts, we elected to evaluate the effectiveness of the reaction by a three-step sequence involving nitrone formation, hydrolysis to the hydroxylamine, and ligation with a peptide α-ketoacid 9 to afford a tetrapeptide 10 (). The purity of the resulting product and its approximate chemical yield were assayed following cleavage from Rink amide MBHA linked resin.

Our interest in the synthesis of hydroxylamines from the corresponding primary amines emerged from our recent discovery of the α-ketoacid–hydroxylamine amide-forming ligation reaction, which allows two unprotected molecules to be chemoselectively conjugated via an amide bond. , While the ligation reaction itself is straightforward, the preparation of peptide chains containing the requisite functional groups at the C-and N-termini presents an unmet synthetic challenge. We have communicated an approach to peptide α-ketoacids, but the only viable route we found to enantiopure N-terminal hydroxylamines is a three step protocol based on a report by Fukuyama., Although very effective for simple amines, it was almost unworkable for complex peptides and could not be extended to solid phase peptide synthesis. We have also found that this method can lead to erosion of the amine stereochemistry if not carefully executed.

Search results for: Text "solution-phase peptide synthesis" - all of the words/ (Protocol search)
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  • Resins, amino acid derivatives, coupling reagents, ..

    Our Chemistry department works with Solution Phase peptide synthesis and can make whatever peptides or ..

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    Peptide synthesis - Wikipedia

  • Methods and Protocols of Modern Solid Phase Peptide ..

    This approach circumvents the comparatively time-consuming isolation of the product peptide from solution after ..

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Protocols - Index Protocol : Protocol Exchange

The Fmoc/TAEA and Bsmoc/TAEA methods for the rapid, continuous solution synthesis of peptide segments are shown to be applicable to the gram-scale synthesis of short peptides as well as, for the first time, to the synthesis of a relatively long (22-mer) segment, (hPTH 13−34). In the latter case the crude product was of significantly greater purity than a sample obtained via a solid-phase protocol. The Bsmoc methodology was optimized by a new technique involving filtration of the growing partially deprotected peptide at each coupling−deprotection cycle through a short column of silica gel.

Peer Reviewed 1 protocol; Subject Term ..

The selective oxidation of primary amines to hydroxylamines is a synthetic transformation that currently lacks a straightforward solution. While oxidations of primary amines to nitro groups, imines, or oximes with both organic and metal-mediated oxidants are well known, there is no general method for interrupting these oxidations at the more reactive and oxidatively labile hydroxylamine stage. Direct methods for the preparation of NOBz derivatives, while convenient for simple substrates, fail with most functionalized amines and lead to imine formation with α-amino acid derivatives. In this communication, we disclose a reagent that makes possible the conversion of primary amines of α-peptides to nitrones and, by hydrolysis, to chiral hydroxylamines via an operationally simple protocol and with retention of stereochemistry ().

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