Side Reactions in Peptide Synthesis

Side Reactions in Peptide Synthesis, based on the author’s academic and industrial experience, and backed by a thorough review of the current literature, provides analysis of, and proposes solutions to, the most frequently encountered side reactions during peptide and peptidomimetic synthesis.

This valuable handbook is ideal for research and process chemists working with peptide synthesis in diverse settings across academic, biotech, and pharmaceutical research and development.

While peptide chemistry is increasingly prevalent, common side reactions and their causes are often poorly understood or anticipated, causing unnecessary waste of materials and delay.

Each chapter discusses common side reactions through detailed chemical equations, proposed mechanisms (if any), theoretical background, and finally, a variety of possible solutions to avoid or alleviate the specified side reaction.

Provides a systematic examination on how to troubleshoot and minimize the most frequent side reactions in peptide synthesisGives chemists the background information and the practical tools they need to successfully troubleshoot and improve resultsIncludes optimization-oriented analysis of side reactions in peptide synthesis for improved industrial process development in peptidyl API (active pharmaceutical ingredient) production Answers the growing, global need for improved, replicable processes to avoid impurities and maintain the integrity of the end product.Presents a thorough discussion of critical factors in peptide synthesis which are often neglected or underestimated by chemists Covers solid phase and solution phase methodologies, and provides abundant references for further exploration

1. Peptide Fragmentation/Deletion
2. Premature FMOC Deprotection
3. Elimination Side Reactions
4. Peptide Global Deprotection/Scavenger-Induced Side Reactions
5. Peptide Rearrangement Side Reactions
6. Side Reactions Occurring at Amino Acid/Peptide Activation Step
7. Intramolecular Cyclization Side Reactions
8. Side Reactions in Amino Groups in Peptide Synthesis
9. Side Reactions in Hydroxyl, Carboxyl, Ester Groups in Peptide Synthesis
10. Oxidation and Reduction Side Reactions in Peptide Synthesis
11. Racemization in Peptide Synthesis
12. Solvent and Residual Impurities in the Reagents Induced Side Reactions
13. Dipeptide Formation Side Reactions (Redundant Amino Acid Incorporation)
14. Reattachment of Peptides to the Solid Supports
15. Addition Side Reactions in Peptide Synthesis
16. Side Reactions in Phosphor Peptides
17. Side Reactions in CYS
18. Protein Fragmentations