Use of 19F NMR spectroscopy to evaluate reactions in solid phase organic synthesis

Svensson, Åsa; Fex, Tomas; Kihlberg, Jan

doi:10.1016/0040-4039(96)01704-2

Cited by 54 publications

(26 citation statements)

References 14 publications

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“…Resin-Bound N-Butyl-N-(2-oxo-2H-1-benzopyran-3-carbonyl)-glycine (21). A solution of salicylaldehyde (83 µL, 0.78 mmol) in freshly distilled CH 3 CN (4 mL) was added to 20 (0.26 mmol, preswollen in dry CH 3 CN).…”

Section: -Fluoro-4-hydroxymethylbenzoic Acid (2) and 2-fluoro-4-hydrmentioning

confidence: 99%

Preparation of Fluorinated Linkers: Use of ¹⁹F NMR Spectroscopy to Establish Conditions for Solid-Phase Synthesis of Pilicide Libraries

2000

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Three fluorinated linkers which are analogues of linkers commonly used in solid-phase peptide synthesis have been prepared. One of the linkers was used in combination with gel-phase 19F NMR spectroscopy to develop conditions for solid-phase synthesis of two libraries of pilicides, i.e. compounds designed to inhibit assembly of adhesive pili in uropathogenic Escherichia coli. Attachment to and cleavage from the linker could be monitored based on the chemical shift of the fluorine atom of the linker. In addition, use of the linker as internal standard allowed quantification and optimization of reactions occurring further away from the linker when fluorinated building blocks were employed. Importantly, high-quality 19F NMR spectra were obtained for compounds linked to a TentaGel resin in a standard NMR tube using an ordinary NMR instrument.

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Section: -Fluoro-4-hydroxymethylbenzoic Acid (2) and 2-fluoro-4-hydrmentioning

confidence: 99%

Preparation of Fluorinated Linkers: Use of ¹⁹F NMR Spectroscopy to Establish Conditions for Solid-Phase Synthesis of Pilicide Libraries

2000

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“…PS-PEG supports are also particularly well suited for on-bead analysis via NMR. The relatively mobile environment created by grafting PEG chains on to the more rigid PS backbone facilitates the application of gel-phase 13 C NMR in a standard spectrometer . The advent of the magic angle spinning technology also allows high-quality 1 H NMR data to be collected; however, specialized equipment is required …”

Section: Owen Gooding Jeff Labadie and John Porco Argogel Resins: Po...mentioning

confidence: 99%

Matrix Assisted Synthetic Transformations: A Mosaic of Diverse Contributions. II. The Pattern Is Completed

Hudson

1999

J. Comb. Chem.

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“…Gel-phase 19 F NMR spectroscopy is a useful and robust method to monitor the progress of reactions on solid support as exemplified in several recent publications [1][2][3][4][5][6][7][8][9]. Fluorinated linkers and building blocks, and fluorinated protective groups allow quantitative and qualitative analysis of the reaction outcome.…”

Section: Introductionmentioning

confidence: 99%

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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Use of 19F NMR spectroscopy to evaluate reactions in solid phase organic synthesis

Cited by 54 publications

References 14 publications

Preparation of Fluorinated Linkers: Use of ¹⁹F NMR Spectroscopy to Establish Conditions for Solid-Phase Synthesis of Pilicide Libraries

Preparation of Fluorinated Linkers: Use of ¹⁹F NMR Spectroscopy to Establish Conditions for Solid-Phase Synthesis of Pilicide Libraries

Matrix Assisted Synthetic Transformations: A Mosaic of Diverse Contributions. II. The Pattern Is Completed

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

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Use of 19F NMR spectroscopy to evaluate reactions in solid phase organic synthesis

Cited by 54 publications

References 14 publications

Preparation of Fluorinated Linkers: Use of 19F NMR Spectroscopy to Establish Conditions for Solid-Phase Synthesis of Pilicide Libraries

Preparation of Fluorinated Linkers: Use of 19F NMR Spectroscopy to Establish Conditions for Solid-Phase Synthesis of Pilicide Libraries

Matrix Assisted Synthetic Transformations: A Mosaic of Diverse Contributions. II. The Pattern Is Completed

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

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Preparation of Fluorinated Linkers: Use of ¹⁹F NMR Spectroscopy to Establish Conditions for Solid-Phase Synthesis of Pilicide Libraries

Preparation of Fluorinated Linkers: Use of ¹⁹F NMR Spectroscopy to Establish Conditions for Solid-Phase Synthesis of Pilicide Libraries

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