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Peptide Synthesis

  1. Thomas Felgenhauer1,
  2. Christopher Schirwitz1,
  3. Frank Breitling2

Published Online: 15 APR 2010

DOI: 10.1002/14356007.a19_157.pub2

Ullmann's Encyclopedia of Industrial Chemistry

Ullmann's Encyclopedia of Industrial Chemistry

How to Cite

Felgenhauer, T., Schirwitz, C. and Breitling, F. 2010. Peptide Synthesis. Ullmann's Encyclopedia of Industrial Chemistry. .

Author Information

  1. 1

    German Cancer Research Centre (DKFZ), Heidelberg, Germany

  2. 2

    Karlsruhe Institute of Technology (KIT), Karlsruhe, Germany

Publication History

  1. Published Online: 15 APR 2010

Chemistry Terms

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The article contains sections titled:

2.Fundamentals of Peptide Synthesis
3.Strategies for Peptide Synthesis
3.1.Solid-Phase Synthesis
3.2.Microwave-Assisted Peptide Synthesis
3.3.Combinatorial Synthesis of Peptides
3.4.Peptide Arrays
3.5.Other Synthetic Methods
4.Chain-Growing-, and Side-Chain Protective Groups
4.1.Protection of the α-Amino Functionality (“Transient Protection”)
4.1.1.Base-Labile Protection of the α-Amino Functionality
4.1.2.Acid-Labile Protection of the α-Amino Functionality
4.1.3.Other Orthogonal Protective Groups for the α-Amino Functionality
4.2.Side-Chain Protective Groups (“Permanent Protection”)
4.2.1.Side-Chain Protective Groups for ω-Carboxylic acids (D, E)
4.2.2.Side-Chain Protective Groups for Amides (N, Q)
4.2.3.Side-Chain Protective Groups for Thioles and Thioethers (C, M)
4.2.4.Side-Chain Protective Groups for the Imidazole Ring (H)
4.2.5.Side-Chain Protection for the Guanidinium Group (R)
4.2.6.Side-Chain Protective groups for ω-Amines (K)
4.2.7.Side-Chain Protection for ω-Hydroxyl Groups (S, T, Y)
4.2.8.Side-Chain Protection for Indole Groups (W)
5.Coupling Methods—Formation of the Peptide Bond
5.1.Diisopropylcarbodiimide (DIC)/N-Hydroxybenzotriazole (HOBt) Activation
5.2.Active Ester Method
5.3.Symmetrical/Asymmetrical (Mixed) Anhydride Method
5.4.Aminium and Phosphonium Activation
5.5.Acid Fluorides
6.Side Reactions
6.1.Enantiomerization, Oxazolone Formation
6.2.Aspartimide Formation
6.3.Ornithine- and δ-Lactam Formation
7.Summary and Outlook