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Custom peptide synthesis - Wikipedia

Peptide synthesis - Wikipedia

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The peptide families in this section are ribosomal peptides,usually with hormonal activity. All of these peptides aresynthesized by cells as longer "propeptides" or "proproteins" andtruncated prior to exiting the cell. They are released into thebloodstream where they perform their signalling functions.

Peptides are synthesized by coupling the carboxyl group of one amino acid to …

SPPS is limited by , and typically peptides and proteins in the range of 70~100 amino acids are pushing the limits of synthetic accessibility. Synthetic difficulty also is sequence dependent; typically peptides and proteins are difficult to make. Longer lengths can be accessed by using to couple two peptides together with quantitative yields.

Liquid-phase peptide synthesis is a classical approach to peptide …

Solid-phase peptide synthesis, pioneered by Robert Bruce Merrifield, caused a …

In peptide synthesis, microwave irradiation has been used to complete long peptide sequences with high degrees of yield and low degrees of racemization. Microwave irradiation during the coupling of amino acids to a growing polypeptide chain is not only catalyzed through the increase in temperature, but also due to the alternating electromagnetic radiation[citation needed] to which the polar backbone of the polypeptide continuously aligns to. Due to the this phenomenon, the microwave energy can prevent aggregation and thus increases yields of the final peptide product. There is however no clear evidence that microwave is better than simple heating and some peptide laboratories regard microwave just as a convenient method for rapid heating of the peptidyl resin. Heating to above 50-55 degrees celcius also prevents aggregation and accelerates the coupling.

Stepwise elongation, in which the amino acids are connected step-by-step in turn, is ideal for small peptides containing between 2 and 100 amino acid residues. Another method is fragment condensation, in which peptide fragments are coupled. Although the former can elongate the peptide chain without , the yield drops if only it is used in the creation of long or highly polar peptides. Fragment condensation is better than stepwise elongation for synthesizing sophisticated long peptides, but its use must be restricted in order to protect against racemization. Fragment condensation is also undesirable since the coupled fragment must be in gross excess, which may be a limitation depending on the length of the fragment.

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The name solid support implies that reactions are carried out on the …

Despite the main advantages of microwave irradiation of peptide synthesis, the main disadvantage is the racemization which may occur with the coupling of cysteine and histidine. A typical coupling reaction with these amino acids are performed at lower temperatures than the other 18 natural amino acids. A number of peptides does not survive microwave synthesis of heating in general. One of the more serious side effects is dehydration (loss of water) which for certain peptides can be almost quantitative like pancreatic polypeptide (PP). This side effect is also seen by simple heating without the use of microwave.

As of January 2009, over 200 microwave peptide synthesizers are in use with the rate of acceptance increasing.[citation needed]

Amino acids have reactive α-carboxylic acid and α-amine groups that allow …
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  • are short chains of amino acid monomers linked by peptide ..

    Liquid-phase synthesis

  • Fluorenylmethyloxycarbonyl chloride

    Solid-phase synthesis

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The t-Boc (tert-butyloxycarbonyl or more simply "Boc") group was commonly used for protecting the terminal amine of the peptide, requiring the use of more acid stable groups for side chain protection in orthogonal strategies. It retains usefulness in reducing of peptides during synthesis. t-Boc groups can be added to amino acids with and a suitable base.

Custom Peptide Synthesis - New England Peptide

Currently, two protecting groups (t-Boc, Fmoc) are commonly used in solid-phase peptide synthesis. Their lability is caused by the group which readily releases CO2 for an irreversible decoupling step.

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Fmoc (9H-fluoren-9-ylmethoxycarbonyl) is currently a widely used protective group that is generally removed from the N terminus of a peptide in the iterative synthesis of a peptide from amino acid units. The advantage of Fmoc is that it is cleaved under very mild basic conditions (e.g. ), but stable under acidic conditions, although this has not always held true in certain synthetic sequences. This allows mild acid labile protecting groups that are stable under basic conditions, such as Boc and benzyl groups, to be used on the side-chains of amino acid residues of the target peptide. This orthogonal protecting group strategy is common in the art of organic synthesis.

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ChemMatrix(R) is a new type of resin which is based on PEG that is crosslinked. ChemMatrix(R) has claimed a high chemical and thermal stability (is compatible with Microwave synthesis) and has shown higher degrees of swellings in , , , , and compared to the polystyrene based resins. ChemMatrix has shown significant improvements to the synthesis of hydrophobic sequences. ChemMatrix is recommended for the synthesis of difficult and long peptides.

In vitro studies demonstrated an increase in synthesis of ..

When Merrifield invented solid-phase peptide synthesis (SPPS) in 1963, it was according to the t-Boc method. (or Boc) stands for (t)ert-(B)ut(o)xy(c)arbonyl. To remove from a growing peptide chain, acidic conditions are used (usually neat ). Removal of side-chain protecting groups and the peptide from the resin at the end of the synthesis is achieved by incubating in anhydrous (which can be dangerous or even deadly), although generally safe, and using only small quantities, HF cleavage needs to be done using specialized equipment, so it is generally disfavored. However for complex syntheses t-Boc synthesis is favourable. In addition, when synthesizing nonnatural peptide analogs which are base-sensitive (such as ), the t-Boc protecting group is necessary.

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