Preparation of large macrocyclic peptides using the oxime resin

Blanchette, Jean-Philippe; Ferland, Patrick; Voyer, Normand

doi:10.1016/j.tetlet.2007.05.033

Cited by 10 publications

(9 citation statements)

References 17 publications

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“…Cyclizative cleavages of cyclopeptides, but not of cyclodepsipeptides, have been accomplished under a variety of reaction conditions. [34][35][36] After some experimentation (Table 2) we found a weakly acidic solution of DIEA (2.2 equiv.) and HOAc (5.5 equiv.)…”

Section: Solid-phase Synthesis On Kaiser Resinmentioning

confidence: 99%

Segment Solid‐Phase Total Synthesis of the Anthelmintic Cyclooctadepsipeptides PF1022A and Emodepside

et al. 2012

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Cyclodepsipeptides of the enniation, PF1022 and verticilide families represent a diverse class of highly interesting natural products with respect to their manifold biological activities. However, until now, no practicable solid‐phase syntheses of these compounds have been accomplished, probably due to the problematic combination of N‐methyl amino acids and hydroxycarboxylic acids. We report herein an efficient synthesis of the anthelmintic PF1022A and its commercial analogue emodepside on Kaiser and Wang resins. Our protocol provides the basis for the solid‐phase synthesis of cyclodepsipeptide libraries with a high probability of anthelmintic, antibacterial or insecticidal activity.

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Section: Solid-phase Synthesis On Kaiser Resinmentioning

confidence: 99%

Segment Solid‐Phase Total Synthesis of the Anthelmintic Cyclooctadepsipeptides PF1022A and Emodepside

et al. 2012

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“…Taking advantage of the dimerization side reaction of Kaiser Oxime resin, Tamaki et al . synthesized 3 by using a high level of loading resin to facilitate intercyclization in 1,4‐dioxane as a mediating solvent (Scheme ) …”

Section: Bacterial Antimicrobial Cyclopeptidesmentioning

confidence: 99%

“…Ta king advantage of the dimerization side reaction of Kaiser Oxime resin, Ta maki et al [135] synthesized 3 by using ah igh level of loading resin to facilitate intercyclization in 1,4-dioxane as amediating solvent (Scheme 2). [136] Ap owerful antibiotic that is representative of the head to side chain cycle topology is the polymyxin family.P olymyxin antibioticsa re isolated from the Gram-positive bacterium Paenibacillus polymyxa,a lso known as B. polymyxa,a nd comprise variousa nalogues, such as polymyxin B( PMB) and polymyxin E2 (colistin B( 4); Figure 3). [137] Colistini sr ich in the non-proteinogenic amino acid Dab;t hus conferring the molecule with additional stability against enzymatic degradation.C olistin shows aw ide range of activity against Gram-positive bacteria by interacting with lipopolysaccharide molecules in their outer membranes, causing an increase in cell membrane permeability,a nd hence,l eakage andc ell death.…”

Section: Homodetic Cyclic Peptidesmentioning

confidence: 99%

Bacteria Hunt Bacteria through an Intriguing Cyclic Peptide

et al. 2018

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In the last few decades, peptides have been victorious over small molecules as therapeutics due to their broad range of applications, high biological activity, and high specificity. However, the main challenges to overcome if peptides are to become effective drugs is their low oral bioavailability and instability under physiological conditions. Cyclic peptides play a vital role in this context because they show higher stability under physiological conditions, higher membrane permeability, and greater oral bioavailability than that of their corresponding linear analogues. In this regard, cyclic antimicrobial peptides (AMPs) have gained considerable attention in the field of novel antibiotic development. Bacterial strains produce cyclic AMPs through two pathways: ribosomal and nonribosomal. This review provides an overview of the chemical classification of cyclic AMPs isolated from bacteria, and provides a description of their biological activity and mode of action.

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“…The different parameters affecting the cyclisation-oligomerisation reaction, whether to favor cyclic monomer or cyclic oligomers formation has been reported. 3 The synthesis of racemic Alloc-Ncy(Tmob)-OH, the resolution of its methyl ester and the demonstration of its application to form a norcysteine bridge in octreotide-amide using the Fmoc strategy on solid phase has been reported. N-Alloc and S-Tmob protection of norcysteine (Ncy) were found to be a preferred choice for Fmoc strategy over three other protected norcysteines synthesised.…”

Section: Solid-phase Synthesismentioning

confidence: 99%

Combinatorial Chemistry Online Volume 9, Issue 8, August 2007

Terrett

2007

Combinatorial Chemistry - an Online Journal

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Preparation of large macrocyclic peptides using the oxime resin

Cited by 10 publications

References 17 publications

Segment Solid‐Phase Total Synthesis of the Anthelmintic Cyclooctadepsipeptides PF1022A and Emodepside

Segment Solid‐Phase Total Synthesis of the Anthelmintic Cyclooctadepsipeptides PF1022A and Emodepside

Bacteria Hunt Bacteria through an Intriguing Cyclic Peptide

Combinatorial Chemistry Online Volume 9, Issue 8, August 2007

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