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.

Includes index.

Title details screen (ScienceDirect, viewed September 9, 2015).

880-01 Cover; Title Page; Copyright Page; Dedication; Contents; Preface; Chapter 1 -- Peptide Fragmentation/Deletion Side Reactions; 1.1 -- Acidolysis of peptides containing N-Ac-N-alkyl-Xaa motif; 1.2 -- des-Ser/Thr impurities induced by O-acyl isodipeptide Boc-Ser/Thr(Fmoc-Xaa)-OH as building block for peptide synthesis; 1.3 -- Acidolysis of -N-acyl-N-alkyl-Aib-Xaa- bond; 1.4 -- Acidolysis of -Asp-Pro- bond; 1.5 -- Autodegradation of peptide N-terminal H-His-Pro-Xaa- moiety; 1.6 -- Acidolysis of the peptide C-terminal N-Me-Xaa; 1.7 -- Acidolysis of peptides with N-terminal FITC modification.

3.3 -- Formation of Trp-EDT and Trp-EDT-TFA adduct in peptide global deprotection3.4 -- Trp dimerization side reaction during peptide global deprotection; 3.5 -- Trp reduction during peptide global deprotection; 3.6 -- Cys alkylation during peptide global deprotection; 3.7 -- Formation of Cys-EDT adducts in peptide global deprotection reaction; 3.8 -- Peptide sulfonation in side chain global deprotection reaction; 3.9 -- Premature Acm cleavage off Cys(Acm) and Acm Sb2s!O migration during peptide global deprotection.

3.10 -- Methionine alkylation during peptide side chain global deprotection with DODT as scavenger3.11 -- Thioanisole-induced side reactions in peptide side chain global deprotection; References; Chapter 4 -- Peptide Rearrangement Side Reactions; 4.1 -- Acid catalyzed acyl Nb2s! migration and the subsequent peptide acidolysis; 4.2 -- Base catalyzed acyl Ob2s! migration; 4.3 -- His-Nim- induced acyl migration; References; Chapter 5 -- Side Reactions Upon Amino Acid/Peptide Carboxyl Activation; 5.1 -- Formation of N-acylurea upon peptide/amino acid-carboxyl activation by DIC.

5.8 -- Peptide chain termination through the formation of peptide N-terminal urea in CDI-mediated coupling reaction.

Includes bibliographical references and index.