Peptide Synthesis

Abstract

The article contains sections titled: 1. Introduction 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

Amino-Acid Adsorption in MFI-Type Zeolites Enabled by the pH-Dependent Ability to Displace Water

“…Amino acids are building blocks of life and are used in biotechnology and industry with a world market larger than 4 million tons per year and an annual growth of 5–8% . For example, the food industry uses phenylalanine for the production of synthetic sweeteners and glutamic acid for the production of flavor enhancers. , Other amino acids are used for cosmetic and pharmaceutical purposes. , Peptides and proteins consist of amino acids and play an important role in different application fields such as medicine and nutrition. − Products such as amino acids, peptides, and proteins are commonly produced biochemically. − However, downstream processing of biochemical streams can be very difficult due to the compound complexity and is often the most costly part of a biochemical process . Consequently, the development of efficient downstream processing is essential to reduce costs in biochemical production .…”

Purity profiling of Peptide Drugs

“…Acid-sensitive linkers contain an acetal, benzyl or trityl functional group and are cleaved by acids like TFA due to the formation of carbocations. Depending on the linker, different functionalities are incorporated [34]. The standard supports in SPSS are the Merrifield resins, which arechloromethylated PS-DVB linker to which a wide variety of additional linkers and amino acids can be attached [35].…”