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Dieckmann cyclization is an intramolecular Claisen condensation of diesters. The reaction occurs in the presence of a base and generates a cyclic β-ketoester as the final product. Commonly, 1, 6 and 1, 7-diesters are preferred substrates for the reaction since the generated five, and six-membered cyclic β-keto esters are particularly more stable.
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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...
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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the...
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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
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Enzyme-catalyzed peptide cyclization.

Marcel Schmidt1, Ana Toplak2, Peter J L M Quaedflieg2

  • 1EnzyPep B.V., Brightlands Campus, Urmonderbaan 22, 6167 RD Geleen, The Netherlands; Van 't Hoff Institute for Molecular Sciences, University of Amsterdam, Science Park 904, 1098 XH Amsterdam, The Netherlands.

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Enzymatic methods offer efficient synthesis of peptide macrocycles, a new class of therapeutics. This review discusses enzymes like sortase A for peptide ligation, accelerating drug development.

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Area of Science:

  • Medicinal Chemistry
  • Biotechnology
  • Biochemistry

Background:

  • Peptide macrocycles show promise as therapeutics.
  • Efficient synthesis and large-scale production are needed.
  • Enzymatic methods offer favorable properties for biocatalysis.

Purpose of the Study:

  • To review novel enzyme-mediated methodologies for peptide macrocycle synthesis.
  • To discuss the advantages and disadvantages of different enzymatic strategies.
  • To highlight the role of enzymes in accelerating cyclic peptide therapeutic development.

Main Methods:

  • Review of literature on enzyme-mediated peptide ligation.
  • Discussion of specific enzymes: sortase A, butelase 1, peptiligase, and omniligase-1.
  • Analysis of enzymatic strategies for complex cyclic peptide generation.

Main Results:

  • Enzymes like sortase A, butelase 1, peptiligase, and omniligase-1 are powerful tools for peptide ligation.
  • Enzymatic strategies can generate cyclic peptides with high biological activity.
  • Enzymatic synthesis complements existing chemical methodologies.

Conclusions:

  • Enzyme-mediated synthesis is a valuable approach for peptide macrocycles.
  • These methods accelerate the development of cyclic peptide therapeutics.
  • Enzymatic strategies offer an efficient alternative for therapeutic peptide production.