NMR Tube Filter Reactor for Solid-Phase Synthesis and Gel-Phase <sup>19</sup>F NMR Spectroscopy

Wallner, Fredrik K.; Elofsson, Mikael

doi:10.1021/cc050144f

Cited by 5 publications

(6 citation statements)

References 36 publications

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“…(3), the Gel-phase 19 F NMR spectra of solid synthesis samples showed line widths similar to those spectra recorded in normal NMR tubes [6]. So reaction sequence on resins (Fig.…”

Section: Nuclear Magnetic Resonance (Nmr) Spectroscopysupporting

confidence: 60%

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Characterizing the Surface Chemistry of Nanoparticles: An Analogy to Solid-Phase Synthesis Samples

Liu¹,

Yan²

2011

CCHTS

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Chemical modifications of nanoparticle's (NP's) surfaces can be used to regulate their activities, remove their toxic effects, and enable them to perform desired functions. Similar to SPS samples, modified NPs also have small-molecules on the surface of a solid support. The need to monitor synthesis, optimize reaction conditions, and characterize the products is quite similar in both situations. FTIR, NMR, MS and other analytical methods have been used as effective methods to analyze surface bound molecules and monitor organic reactions directly, or indirectly, on a solid phase of a resin or a NPs.

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“…(3), the Gel-phase 19 F NMR spectra of solid synthesis samples showed line widths similar to those spectra recorded in normal NMR tubes [6]. So reaction sequence on resins (Fig.…”

Section: Nuclear Magnetic Resonance (Nmr) Spectroscopysupporting

confidence: 60%

“…(Reprinted with permission from Ref. [6] © 2006 American Chemical Society) lowest detection limit. Therefore, the elemental analysis results strongly indicated that the cleavage reaction was complete.…”

Section: Mass Spectroscopy (Ms)mentioning

confidence: 99%

Characterizing the Surface Chemistry of Nanoparticles: An Analogy to Solid-Phase Synthesis Samples

Liu¹,

Yan²

2011

CCHTS

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“…Subsequently the model peptide amide Ac-L-Val-L-Val-NH 2 12 where the N-terminal valine was protected with the novel Fde group was synthesized (Scheme 2). The solid-phase synthesis was carried out in a continuous flow NMR-tube reactor [18]. First, resin 7 was prepared from TentaGel coupled with activated Fmoc-L-mF-Phe-OH containing the fluorinated marker, followed by the Rink amide linker.…”

Section: Resultsmentioning

confidence: 99%

“…Peptide chain assembly was carried out in a NMR-tube filter reactor [18] on a TentaGel HL NH 2 resin (0.35 mmol/g, Rapp Polymere, Germany) with circulating reagent solutions. Circulation and washing were performed with the FMI Lab Pump, model RP-G150 (Fluid Metering, Inc.), with custom made transformator to allow for variable speed.…”

Section: Solid-phase Synthesismentioning

confidence: 99%

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Synthesis and application of N‐[1‐(4‐(4‐fluorophenyl)‐2,6‐dioxocyclohexylidene)ethyl] (Fde)‐protected amino acids for optimization of solid‐phase peptide synthesis using gel‐phase ¹⁹F NMR spectroscopy

Pudelko

Qian

Elofsson

2009

Journal of Peptide Science

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N-[1-(4-(4-fluorophenyl)-2,6-dioxocyclohexylidene)ethyl] (Fde) protected amino acids have been prepared and applied in solid-phase peptide synthesis monitored by gel-phase (19)F NMR spectroscopy. The Fde protective group could be cleaved with 2% hydrazine or 5% hydroxylamine solution in DMF as determined with gel-phase (19)F NMR spectroscopy. The dipeptide Ac-L-Val-L-Val-NH(2) 12 was constructed using Fde-L-Val-OH and no noticeable racemization took place during the amino acid coupling with N,N'-diisopropylcarbodiimide and 1-hydroxy-7-azabenzotriazole or Fde deblocking. To extend the scope of Fde protection, the hydrophobic nonapeptide LLLLTVLTV from the signal sequence of mucin MUC1 was successfully prepared using Fde-L-Leu-OH at diagnostic positions.

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Application of gel‐phase ¹⁹F NMR spectroscopy for optimization of solid‐phase synthesis of a hydrophobic peptide from the signal sequence of the mucin MUC1

Pudelko

Kihlberg

Elofsson

2007

Journal of Peptide Science

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This paper describes the manual Fmoc/t-Bu solid-phase synthesis of a difficult nine-residue hydrophobic peptide LLLLTVLTV from one of the signal sequences that flank the tandem repeat of the mucin MUC1. Gel-phase 19F NMR spectroscopy was used as a straightforward method for optimization of the solid-phase synthesis. Different approaches were applied for comparative studies. The strategy based on modified solid-phase conditions using DIC/HOAt for coupling, DBU for Fmoc deprotection, and the incorporation of the pseudo proline dipeptide Fmoc-Leu-Thr(psiMe, Me pro)-OH as a backbone-protecting group was found to be superior according to gel-phase 19F NMR spectroscopy. Implementation of the optimized Fmoc protocol enabled an effective synthesis of signal peptide LLLLTVLTV.

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NMR Tube Filter Reactor for Solid-Phase Synthesis and Gel-Phase ¹⁹F NMR Spectroscopy

Cited by 5 publications

References 36 publications

Characterizing the Surface Chemistry of Nanoparticles: An Analogy to Solid-Phase Synthesis Samples

Characterizing the Surface Chemistry of Nanoparticles: An Analogy to Solid-Phase Synthesis Samples

Synthesis and application of N‐[1‐(4‐(4‐fluorophenyl)‐2,6‐dioxocyclohexylidene)ethyl] (Fde)‐protected amino acids for optimization of solid‐phase peptide synthesis using gel‐phase ¹⁹F NMR spectroscopy

Application of gel‐phase ¹⁹F NMR spectroscopy for optimization of solid‐phase synthesis of a hydrophobic peptide from the signal sequence of the mucin MUC1

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NMR Tube Filter Reactor for Solid-Phase Synthesis and Gel-Phase 19F NMR Spectroscopy

Cited by 5 publications

References 36 publications

Characterizing the Surface Chemistry of Nanoparticles: An Analogy to Solid-Phase Synthesis Samples

Characterizing the Surface Chemistry of Nanoparticles: An Analogy to Solid-Phase Synthesis Samples

Synthesis and application of N‐[1‐(4‐(4‐fluorophenyl)‐2,6‐dioxocyclohexylidene)ethyl] (Fde)‐protected amino acids for optimization of solid‐phase peptide synthesis using gel‐phase 19F NMR spectroscopy

Application of gel‐phase 19F NMR spectroscopy for optimization of solid‐phase synthesis of a hydrophobic peptide from the signal sequence of the mucin MUC1

Contact Info

Product

Resources

About

NMR Tube Filter Reactor for Solid-Phase Synthesis and Gel-Phase ¹⁹F NMR Spectroscopy

Synthesis and application of N‐[1‐(4‐(4‐fluorophenyl)‐2,6‐dioxocyclohexylidene)ethyl] (Fde)‐protected amino acids for optimization of solid‐phase peptide synthesis using gel‐phase ¹⁹F NMR spectroscopy

Application of gel‐phase ¹⁹F NMR spectroscopy for optimization of solid‐phase synthesis of a hydrophobic peptide from the signal sequence of the mucin MUC1