05537cam a2200589Ki 4500 ocn920551933 OCoLC 20190328114812.0 m o d cr cnu---unuuu 150909t20152016enk o 001 0 eng d OPELS eng rda pn OPELS YDXCP OCLCF N$T IDEBK EBLCP OCLCQ ESU DEBBG B3G BRA MERUC COS COF U3W D6H ESEHU AU@ OCLCQ WYU OCLCA MERER OCLCO OCLCA OCLCQ (S 1066447827 9780128011812 (electronic bk.) 0128011815 (electronic bk.) 9780128010099 0128010096 (OCoLC)920551933 (OCoLC)1066447827 QP552.P4 2016 A-909 QU 68 SCI 007000 bisacsh 572/.65 23 Yang, Yi, author. Side reactions in peptide synthesis / [electronic resource] Yi Yang. London, UK : Academic Press is an imprint of Elsevier, 2015. �2016 1 online resource text txt rdacontent computer c rdamedia online resource cr rdacarrier 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. Peptides Synthesis. Peptides Synthesis. fast (OCoLC)fst01057580 SCIENCE Life Sciences Biochemistry. bisacsh Peptide Biosynthesis. (DNLM)D010452 Peptides chemistry. (DNLM)D010455Q000737 Drug-Related Side Effects and Adverse Reactions. (DNLM)D064420 Electronic books. Electronic book. ScienceDirect http://www.sciencedirect.com/science/book/9780128010099 505-00/(S 1.8 -- Acidolysis of thioamide peptide1.9 -- Deguanidination side reaction on Arg; 1.10 -- DKP (2,5-diketopiperazine) formation; References; Chapter 2 -- (Sb(B-Elimination Side Reactions; 2.1 -- (Sb(B-Elimination of Cys sulfhydryl side chain; 2.2 -- (Sb(B-Elimination of phosphorylated Ser/Thr; References; Chapter 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. 505-01/(S 5.2 -- Uronium/Guanidinium salt coupling reagents-induced amino group guanidination side reactions5.3 -- (Se(B-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-(Sb(B-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. 247157 247157