Side Reactions in Peptide Synthesis by Yi Yang

By Yi Yang

Side Reactions in Peptide Synthesis, based at the author’s educational and commercial adventure, and subsidized by way of a radical assessment of the present literature, presents research of, and proposes suggestions to, the main often encountered part reactions in the course of peptide and peptidomimetic synthesis.

This priceless instruction manual is perfect for study and approach chemists operating with peptide synthesis in different settings throughout educational, biotech, and pharmaceutical learn and improvement.

While peptide chemistry is more and more standard, universal facet reactions and their motives are frequently poorly understood or expected, inflicting pointless waste of fabrics and hold up.

Each bankruptcy discusses universal part reactions via distinct chemical equations, proposed mechanisms (if any), theoretical heritage, and at last, a number of attainable recommendations to prevent or alleviate the desired aspect response.

  • Provides a scientific exam on find out how to troubleshoot and reduce the main widespread aspect reactions in peptide synthesis
  • Gives chemists the heritage details and the sensible instruments they should effectively troubleshoot and enhance results
  • Includes optimization-oriented research of part reactions in peptide synthesis for greater commercial procedure improvement in peptidyl API (active pharmaceutical aspect) construction
  • Answers the turning out to be, international want for more suitable, replicable methods to prevent impurities and keep the integrity of the top product.
  • Presents a radical dialogue of severe elements in peptide synthesis that are frequently ignored or underestimated via chemists
  • Covers strong part and answer part methodologies, and offers considerable references for additional exploration

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Extra info for Side Reactions in Peptide Synthesis

Example text

On the contrary, if the peptide assembly goes beyond the subjected Ser/Thr(PO3R,H) residue, that is to say, when the phosphoamino acid is located in the endo position in the corresponding peptide sequence, the b-elimination side reaction on this residue upon base treatment will be attenuated. 1. However, this discrepancy alleges that utmost caution is supposed to be exerted to the step of Fmoc deprotection from Fmoc-Ser/Thr(PO3R,H)peptide derivative. 27 The extent of b-elimination on phosphopeptides is directly proportional to the duration of base treatment.

Peptide Fragmentation/Deletion Side Reactions Chapter | 1 27 The choice of coupling reagents will affect the extent of the DKP formation. 75 The preference is attributed to the intrinsic property of carbodiimide derivatives that they could mediate the amino acid couplings in the absence of tertiary bases. DKP side reactions are restrained in this manner by virtue of utilization of carbodiimide coupling reagents for the amino acid couplings at sensitive sequences. Since DKP formation might prefer to take place on C-terminal dipeptide acid sequence, the properties of spacers on the solid support could decisively determine the propensity of the referred peptide to suffer from the DKP formation during SPPS.

24. Firstly, pNZ is reduced to p-aminobenzyloxycarbonyl that subsequently undergoes spontaneous collapse to afford quinone imine methide and the corresponding carbamate derivative. The latter is converted to amine via decarboxylation process. Similarly, SnCl2 could reduce Na-pNZ derivative to the corresponding amine in the presence of an acidic catalyst. The advantages of pNZ over Fmoc are mainly reflected by its removal condition that is devoid of base treatment, facilitating in this manner the suppression of DKP formation that is catalyzed by bases like piperidine.

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