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A straightforward method for automated Fmoc-based synthesis of bio-inspired peptide crypto-thioesters.

ABSTRACT: Despite recent advances, the direct Fmoc-based solid phase synthesis of peptide ?-thioesters for the convergent synthesis of proteins via native chemical ligation (NCL) remains a challenge in the field. We herein report a simple and general methodology, enabling access to peptide thioester surrogates. A novel C-terminal N-(2-hydroxybenzyl)cysteine thioesterification device based on an amide-to-thioester rearrangement was developed, and the resulting peptide crypto-thioesters can be directly used in NCL reactions with fast N ? S shift kinetics at neutral pH. These fast kinetics arise from our bio-inspired design, via intein-like intramolecular catalysis. Due to a well-positioned phenol moiety, an impressive >50 fold increase in the kinetic rate is observed compared to an O-methylated derivative. Importantly, the synthesis of this new device can be fully automated using inexpensive commercially available materials and does not require any post-synthetic steps prior to NCL. We successfully applied this new method to the synthesis of two long naturally-occurring cysteine-rich peptide sequences.

SUBMITTER: Terrier VP

PROVIDER: S-EPMC5952550 | biostudies-other | 2016 Jan

REPOSITORIES: biostudies-other

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A straightforward method for automated Fmoc-based synthesis of bio-inspired peptide crypto-thioesters.

Terrier Victor P VP Adihou Hélène H Arnould Mathieu M Delmas Agnès F AF Aucagne Vincent V

Chemical science 20150923 1

Despite recent advances, the direct Fmoc-based solid phase synthesis of peptide α-thioesters for the convergent synthesis of proteins <i>via</i> native chemical ligation (NCL) remains a challenge in the field. We herein report a simple and general methodology, enabling access to peptide thioester surrogates. A novel C-terminal <i>N</i>-(2-hydroxybenzyl)cysteine thioesterification device based on an amide-to-thioester rearrangement was developed, and the resulting peptide crypto-thioesters can be ...[more]

PMID: 29861986

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Project description:Ceramic materials possessing the properties of high-strength and rigidity are widely used in industry. The shell nacre has a layered structure containing both macroscopic and microscopic levels and is equipped with superior qualities regarding hardness and strength. Therefore, the ceramic composites with a nacre-like layered structure have the potential to be utilized as sliding bearings employed in the harsh conditions of wells. For the purpose of this paper, a porous Al?O? ceramics skeleton with nanometer powder is prepared using the freeze-casting method. Then the porous ceramic skeleton is filled with polymer polymethyl methacrylate (PMMA) through mass polymerization to produce a bionic Al?O?/PMMA composite with a lamellar structure. The properties of the prepared composite are determined by the analysis of micro-hardness, fracture toughness, friction coefficient, wear scar diameter, and the morphology of the worn surface. Consequent results indicate that elevation in the A1?O? powder, which acts as the initial solid phase content, prompts the ceramic slurry to exhibit an increase in viscosity and a gradual decrease in the pore size of the ceramic skeleton. The prepared layered Al?O?/PMMA composite possesses high fracture toughness, which closely resembles that of Al, is approximately four times that of the matrix of the Al?O? ceramics and 16 times that of the PMMA. Three kinds of composites containing different solid phase content are subjected to testing involving lubrication by water-based drilling fluid to determine the friction coefficient of each. The results indicate that an increased load leads to a decreased friction coefficient while the impact of speed is not evident. Under dry conditions, the friction coefficient of three different composites tested, declines with elevated load and speed. With the use of water-based drilling fluid as lubrication, the wear scar diameter increases at higher speed, while dry conditions denote increased load. Abrasive wear is determined to be the principal form of erosion of layered Al?O?/PMMA composites.

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A straightforward method for automated Fmoc-based synthesis of bio-inspired peptide crypto-thioesters.

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A straightforward method for automated Fmoc-based synthesis of bio-inspired peptide crypto-thioesters.

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