Preface
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—acyllsodipeptide 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
1.8 Acidolysis of Thioamide Peptide
1.9 Deguanidination Side Reaction on Arg
1.10 DKP（2，5—Diketopiperazine）Formation
References
2 β—Elimination Side Reactions
2.1 β—Elimination of Cys Sulfhydryl Side Chain
2.2 β—Elimination of Phosphorylated Ser／Thr References
3 Peptide Global Deprotection／Scavenger—Induced Side Reactions
3.1 Tert—Butylation Side Reaction on Trp During Peptide Global Deprotection
3.2 Trp Alkylation by Resin Linker Cations During Peptide Cleavage／Global Deprotection
3.3 Formation of Trp—EDT and Trp—EDT—TFA Adduct in Peptide Global Deprotection
3.4 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 S→O Migration During Peptide Global Deprotection
3.10 Methionine Alkylation During Peptide Side Chain Global Deprotection with DODT as Scavenger
3.11 Thioanisole—Induced Side Reactions in Peptide Side Chain Global Deprotection
References
4 Peptide Rearrangement Side Reactions
4.1 Acid Catalyzed Acyl N→O Migration and the Subsequent Peptide Acidolysis
4.2 Base Catalyzed Acyl O→N Migration
4.3 His—Nim—Induced Acyl Migration
References
5 Side Reactions Upon Amino Acid／Peptide Carboxyl Activation
5.1 Formation of N—Acylurea Upon Peptide／Amino Acid—Carboxyl Activation by DIC
5.2 Uronium／Guanidinium Salt Coupling Reagents—Induced Amino Group Guanidination Side Reactions
5.38—Lactam Formation Upon Arg Activation Reaction
5.4 NCA Formation Upon Boc／Z—Amino Acid Activation
5.5 Dehydration of Side Chain—Unprotected Asn／Gln During Carboxyl—Activation
5.6 Formation of H—β—Ala—OSu from HOSu—Carbodiimide Reaction During Amino Acid Carboxyl—Activation
5.7 Benzotriazinone Ring Opening and Peptide Chain Termination During Carbodiimide／HOOBt Mediated Coupling Reactions
5.8 Peptide Chain Termination Through the Formation of Peptide N—Terminal Urea in CDI—Mediated Coupling Reaction
5.9 Guanidino or Hydantoin—2—Imide Formation from Carbodiimide and Na Group on Amino Acid／Peptide
5.10 Side Reactions—Induced by Curtius Rearrangement on Peptide Acyl Azide
5.11 Formation of Pyrrolidinamide—Induced by Pyrrolidine Impurities in Phosphonium Salt
References
6 Intramolecular Cyclization Side Reactions
6.1 AspartimideFormation
6.1.1 Factors That Influence Aspartimide Formation
6.1.2 Solutions for Aspartimide Formation
6.2 Asn／Gln Deamidation and Other Relevant Side Reactions
6.2.1 Mechanism of Asn／Gln Deamidation
6.2.2 Factors Impacting on Asn／Gln Deamidation
6.2.3 Influences of Asn／Gln Deamidation on Peptide Chemical Synthesis
6.3 Pyroglutamate Formation
6.4 Hydantoin Formation
6.5 Side Reactions on N—Terminal Cys（Cam）and N—Bromoacetylated Peptide
References
7 Side Reactions on Amino Groups in Peptide Synthesis
7.1 Nα—Acetylation Side Reactions
7.2 Trifluoroacetylation Side Reactions
7.3 Formylation Side Reactions
7.3.1 Trp（For）—Induced Peptide Formylation
7.3.2 Formic Acid—Induced Peptide Formylation
7.3.3 DMF—Induced Peptide Formylation
7.4 Peptide N—Alkylation Side Reactions
7.4.1 Chloromethyl Resin Induced Peptide N—Alkylation Side Reactions
7.4.2 Peptide N—Alkylation During Deblocking of Nα—Urethane Protecting Group
7.4.3 Peptide N—Alkylation During Global Deprotection
7.4.4 N—Alkylation Syde Reaction on N—Terminal His via Acetone—Mediated Enamination
7.5 Side Reactions During Amino Acid Nα—Protection（Fmoc—OSu Induced Fmoc—β—Ala—OH and Fmoc—β—Ala—AA—OH Dipeptide Formation）
References
8 Side Reactions on Hydroxyland Carboxyl Groups in Peptide Synthesis
8.1 Side Reactions on Asp／Glu Side Chain and Peptide Backbone Carboxylate
8.1.1 Base—Catalyzed Asp／Glu（OBzl）Transesterification Side Reaction During the Loading of Chloromethyl Resin
8.1.2 Esterification Side Reactions on Asp／Glu During Peptidyl Resin Cleavage and Product Purification
8.2 Side Reactions on Ser／Thr Side Chain Hydroxyl Groups
8.2.1 Alkylation Side Reactions on Ser／Thr Side Chain Hydroxyl Groups
8.2.2 Acylation Side Reactions on Ser／Thr Side Chain Hydroxyl Groups
8.2.3 β—Elimination Side Reactions on Ser／Thr
8.2.4 N—Terminal Ser／Thr—Induced Oxazolidone Formation Side Reactions
8.2.5 Ser／Thr—Induced Retro Aldol Cleavage Side Reaction References
9 Peptide Oxidation／Reduction Side Reactions
9.1 Oxidation Side Reactions on Cys
9.2 Oxidation Side Reactions on Met
9.3 Oxidation Side Reactions on Trp
9.4 Oxidation Side Reactions on Other Amino Acids and at Nonsynthetic Steps
9.5 Peptide Reduction Side Reactions
References
10 Redundant Amino Acid Coupling Side Reactions
10.1 Dipeptide Formation During Amino Acid Nα—Fmoc Derivatization
10.2 Redundant Amino Acid Coupling via Premature Fmoc Deprotection
10.2.1 Lys—Nε—Induced Fmoc Premature Cleavage
10.2.2 Nα—Proline—Induced Fmoc Premature Cleavage
10.2.3 DMF／NMP—Induced Fmoc Premature Cleavage
10.2.4 Residual Piperidine—Induced Fmoc Premature Cleavage
10.2.5 DMAP／DIEA—Induced Fmoc Premature Cleavage
10.2.6 Hydrogenation—Induced Fmoc Premature Cleavage
10.2.7 Fmoc Deblocking in the Starting Material
10.3 Redundant Amino Acid Coupling Induced by NCA Formation
10.4 His—Nim Promoted Gly Redundant Incorporation
10.5 Redundant Coupling Induced by the Undesired Amino Acid—CTC Resin Cleavage
10.6 Redundant Amino Acid Coupling Induced by Insuffiaent Resin Rinsing
10.7 Redundant Amino Aad Coupling Induced by Overacylation Side Reaction
References
……
11 Peptide Racemization
12 Side Reactions in Peptide Phosphorylation
13 Cys Disulfide—Related Side Reactions in Peptide Synthesis
14 Solvent—Induced Side Reactions in Peptide Synthesis
Appendix Ⅰ Molecular Weight Deviation of Peptide Impurity
Appendix Ⅱ List of Abbreviations
Subject Index
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