NF-31 color test uncovers ‘hidden’ alcohol functionalities in PEG-based resins for solid phase peptide synthesis

Carrette, Lieselot L. G.; Verzele, Dieter; Madder, Annemieke

doi:10.1016/j.tetlet.2010.02.040

Cited by 6 publications

(3 citation statements)

References 17 publications

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“…The most recent PEG polymers have been reported to efficiently reduce hydrophobic peptide aggregation through their increased hydrophilic character 30. However, as we have shown earlier, with these more recently developed resins, monitoring of the completion of reactions can be compromised 31. Therefore, we opted for the PEG‐grafted polystyrene Tentagel support from Rapp 32.…”

Section: Resultsmentioning

confidence: 99%

Peptidosteroid Tweezers Revisited: DNA Binding Through an Optimised Design

2014

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A dipodal peptidosteroid based on a deoxycholic acid scaffold was designed as a transcription factor model to study, and ultimately interfere in, selective protein–DNA interactions. In this paper, the selective binding of such a dipodal peptidosteroid to its DNA binding site is described for the first time, thus proving the concept and confirming the potential of the design. To achieve this, two 25‐mer peptides were synthesized in parallel and in close proximity on a rigid amphiphilic scaffold, attached by flexible linkers. Peptide aggregation complicated the synthesis under conventional conditions to such an extent that optimization and the use of microwave assistance were required for a successful synthesis. As such, this synthesis is a good model to showcase the beneficial effects of microwave assistance in peptide synthesis.

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Section: Resultsmentioning

confidence: 99%

Peptidosteroid Tweezers Revisited: DNA Binding Through an Optimised Design

2014

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“…Furthermore, it is advisable to check the result of ninhydrin test with the help of a microscope. Conversely, the NF‐31 assay, a more sensitive test that is especially suitable with sterically hindered secondary and aromatic amines, could give rise to false positive results as a result of the reactive residual alcohols originated by resin elaboration24.…”

Section: Limitationsmentioning

confidence: 99%

ChemMatrix^® for complex peptides and combinatorial chemistry

García-Ramos¹,

Paradís-Bas²,

Tulla‐Puche³

et al. 2010

Journal of Peptide Science

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CM resin is a totally PEG-based resin, made exclusively from primary ether bonds and therefore highly chemically stable. Compared to other PEG resins, it exhibits good loading and is user friendly because of its free-flowing form upon drying. It shows improved performance over PS resins for the preparation of hydrophobic, highly structured poly-Arg peptides. In combination with ψPros, it allows the synthesis of small proteins such as the chemokine RANTES. Like other PEG-based resins, CM resin swells well in biocompatible solvents such as water, thereby allowing on-bead screening. Furthermore, the high loading of this resin permits the use of a tiny quarter of a bead as a microreactor for HPLC and MALDI-TOF analysis, thus further extending its applications in the field of combinatorial chemistry.

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“…May give positive results for free hydroxyl groups even without DMAP 18. Not commercially available.…”

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confidence: 99%