A useful method for the preparation of fully protected peptide acids and esters

Pichette, André; Voyer, Normand; Larouche, Rémi; Meillon, Jean‐Christophe

doi:10.1016/s0040-4039(97)00071-3

Cited by 17 publications

(14 citation statements)

References 11 publications

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“…[31][32][33] The reactivity of the oxime ester towards nucleophiles also allows cyclizative cleavage, which releases the cyclodepsipeptide directly into solution without the need for an additional cyclization reaction. A limited loading of the resin (0.3 mmol/g resin) provides the high-dilution environment needed for the macrocyclization reaction.…”

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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“…While a long linker between the synthetic dendrimer and resin has been indicated to effectively overcome such steric hindrance by increasing the reaction surface area, it has unfortunately also been shown to raise the risk of interactions between neighboring molecules on the same resin . For our study, we used the Kaiser oxime resin because it can be cleaved with a variety of nucleophilic agents . There are two available sizes, 100–200 mesh or 200–400 mesh.…”

Section: Resultsmentioning

confidence: 99%

“…[23] For our study, we used the Kaiser oxime resin because it can be cleaved with a variety of nucleophilic agents. [24][25][26] There are two available sizes, 100-200 mesh or 200-400 mesh. Based on the above considerations, the Kaiser oxime resin with 100-200 mesh would thus be considered to be the better one for constructing high-generation dendrimers, and was used in this investigation.…”

Section: Solid-phase Dendrimer Synthesismentioning

confidence: 99%

Solid‐Phase Synthesis of a Seventh‐Generation Inverse Poly(amidoamine) Dendrimer: Importance of the Loading Ratio on the Resin

Kao

Huang

Chen

2017

Macromol. Rapid Commun.

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Here, this study overcomes the current barriers to efficient solid-phase synthesis of high-generation dendrimers by decreasing the loading ratio on the resin. G7 inverse poly(amidoamine) dendrimer is now prepared, for the first time, through a solid-phase synthesis using only 50% of the available reactive sites and by choosing a large resin. This preparation takes only 15 d to afford highly pure product in 80% yield with precipitation being the only purification procedure used. The results clearly show the amount of the initial monomer loaded on the resin to be a vital factor for the ability to use solid-phase synthesis to produce large dendrimers. This finding also sets stage for the applications of solid-phase synthesis for the preparation of other macromolecules.

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“…KOR has been used successfully for preparing C-terminal free and modified protected peptides because it forms with the growing peptide an oxime ester susceptible to attack by any nucleophile under acid or base conditions [8,18,26,27]. Among the procedures used to prepare protected peptide acids [18,19,28,29], we chose those comprising a single step: hydroxide-ion-promoted hydrolysis of the oxime ester bond (procedure 1; [19]) and DBU-promoted hydrolysis of the oxime ester linkage (procedure 2; [18]). We also employed procedure 3, which is based on our previous observations that hydrolysis [20] and methanolysis [25,30] of the oxime ester bond of a peptide-KOR can be assisted by Ca +2 .…”

Section: Resultsmentioning

confidence: 99%

“…Promoted by DBU (adapted from [18]). The peptide-KOR (17.5 µmol) was suspended in 1 ml of 15% H 2 O/THF in the absence or presence of DBU (35.0 µmol).…”

Section: Peptide Detachment From Resinsmentioning

confidence: 99%

Comparison of procedures for directly obtaining protected peptide acids from peptide‐resins

Proti

Remuzgo

Miranda

2007

Journal of Peptide Science

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The preparation of small-sized protected peptide acids related to cholecystokinin and gomesin was attempted using peptide-Kaiser oxime resins (KOR) as starting materials. For comparison, peptide-2-Cl-trityl resin (CLTR) was also employed. While peptide detachment from KOR was achieved through the oxime ester bond hydrolysis mediated by DBU, hydroxide ion or Ca(+2) ion, peptide release from CLTR was accomplished through acid-catalysed hydrolysis of the peptide-resin ester linkage. Amino acid analysis of the peptide-resins before and after peptide release allowed the calculation of the reaction yields. RP-HPLC and LC/ESI-MS of the resulting crude peptides allowed estimation of their quality. The data collected indicated that: (i) among the procedures used for peptide displacement from KOR, the one employing DBU was the most efficient since it furnished all model protected peptide acids with the highest quality in a very short time; (ii) although slow, Ca(+2)-assisted peptide detachment from KOR was selective and was suitable for generating high-quality protected peptide acids containing up to five residues; (iii) even though the protocols employed for peptide release from CLTR have shown to be appropriate, the one employing 1% TFA/DCM was the most productive; (iv) in terms of product quality, DBU-catalysed peptide detachment from KOR was similar to TFA-catalysed peptide release from CLTR although the latter was more productive. These findings are relevant to peptide chemists in general, but especially to those interested in preparing acyl donors for convergent peptide syntheses by the t-Boc chemistry.

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A useful method for the preparation of fully protected peptide acids and esters

Cited by 17 publications

References 11 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

Solid‐Phase Synthesis of a Seventh‐Generation Inverse Poly(amidoamine) Dendrimer: Importance of the Loading Ratio on the Resin

Comparison of procedures for directly obtaining protected peptide acids from peptide‐resins

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