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Related Concept Videos

Peptide Bonds02:43

Peptide Bonds

A peptide bond covalently attaches amino acids through a dehydration reaction. One amino acid's carboxyl group and another amino acid's amino group combine, releasing a water molecule. The resulting bond is the peptide bond. The products that such linkages form are peptides. As more amino acids join this growing chain, the resulting chain is a polypeptide. Each polypeptide has a free amino group at one end. This end has the N-terminal, or the amino-terminal, and the other end has a free...
Preparation of Amides01:29

Preparation of Amides

Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
Peptidoglycan Synthesis01:28

Peptidoglycan Synthesis

Structure of PeptidoglycanPeptidoglycan is a vital structural component of the bacterial cell wall, providing mechanical strength and shape to the cell. It consists of repeating units of two sugars—N-acetylglucosamine (NAG) and N-acetylmuramic acid (NAM)—linked by β-1,4 glycosidic bonds. These sugar chains are cross-linked by short peptide chains, forming a mesh-like polymer that surrounds the bacterial plasma membrane.Cytoplasmic Phase – Precursor SynthesisPeptidoglycan biosynthesis begins in...
Production of Pharmaceuticals01:30

Production of Pharmaceuticals

Industrial insulin production uses genetically engineered E. coli expressing a proinsulin gene controlled by a tryptophan promoter and containing a methionine linker for later cleavage. The cells also carry ampicillin resistance for selective growth. Seed cultures are stored at −80 °C and production begins by thawing a small amount to inoculate starter cultures, which are progressively scaled to a 50,000-L bioreactor. In the bioreactor, E. coli grow in nutrient-rich media under sterile, tightly...
Preparation of Epoxides03:00

Preparation of Epoxides

Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Amino Acid Biosynthetic Pathways01:29

Amino Acid Biosynthetic Pathways

Amino acid biosynthesis is essential for cell growth, protein synthesis, and metabolic regulation. Cells generate essential and non-essential amino acids from metabolic intermediates to sustain vital biological functions. These intermediates originate from key metabolic pathways: glycolysis, the tricarboxylic acid (TCA) cycle, and the pentose phosphate pathway. Important precursors include α-ketoglutarate, pyruvate, oxaloacetate, phosphoenolpyruvate, and erythrose-4-phosphate, which provide...

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An Inexpensive Adaptation of a Commercial Microwave Reactor for Solid Phase Peptide Synthesis
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Linkers, resins, and general procedures for solid-phase peptide synthesis.

Pernille Tofteng Shelton1, Knud J Jensen

  • 1IGM, Faculty of Life Sciences, University of Copenhagen, Zealand Pharma, Glostrup, Denmark.

Methods in Molecular Biology (Clifton, N.J.)
|August 15, 2013
PubMed
Summary

This chapter details solid-phase peptide synthesis (SPPS) using the Fmoc protecting group. It covers essential resins, linkers, and assembly methods for creating peptides with various C-terminal modifications.

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Area of Science:

  • Organic Chemistry
  • Biochemistry
  • Synthetic Chemistry

Background:

  • Solid-phase peptide synthesis (SPPS) is a cornerstone technique in peptide chemistry.
  • The use of the Fmoc (9-fluorenylmethoxycarbonyl) group offers advantages for N(α)-protection.
  • Selecting appropriate resins and linkers is critical for successful peptide synthesis outcomes.

Purpose of the Study:

  • To provide fundamental protocols for Fmoc-based solid-phase peptide synthesis (Fmoc-SPPS).
  • To guide the selection of resins and linkers for synthesizing peptides with diverse C-terminal functionalities.
  • To present standardized operational procedures for general SPPS.

Main Methods:

  • Detailed description of resin types and their handling in SPPS.
  • Explanation of linker chemistries for attaching peptides to solid supports.
  • Step-by-step protocols for peptide chain assembly using Fmoc-SPPS.
  • Methods for synthesizing peptides with C-terminal amides and carboxylic acids.

Main Results:

  • Comprehensive overview of commonly used resins and linkers in Fmoc-SPPS.
  • Established protocols for standard solid-phase peptide synthesis operations.
  • Demonstrated applicability for peptides with C-terminal amides and carboxylic acids.

Conclusions:

  • Proper selection of resins and linkers is paramount for successful Fmoc-SPPS.
  • The chapter provides a robust foundation for executing general solid-phase peptide synthesis.
  • Standardized protocols ensure reproducibility and efficiency in peptide synthesis.