Fluorinated linkers for monitoring solid-phase synthesis using gel-phase 19F NMR spectroscopy

Svensson, Åsa; Bergquist, Karl‐Erik; Fex, Tomas; Kihlberg, Jan

doi:10.1016/s0040-4039(98)01541-x

Cited by 35 publications

(39 citation statements)

References 5 publications

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“…Resin-Bound 3-Fluoro-4-(hydroxymethyl)phenoxyacetic Acid (17). DIC (99 µL, 0.64 mmol) was added to an ice-cold solution of pentafluorophenol (187 mg, 1.00 mmol) in EtOAc (5 mL).…”

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

confidence: 99%

“…It is also an advantage if the linker can serve analytical purposes. We, 17 and later others, 18 have disclosed preliminary results concerning development of fluorine-derivatized solid supports and their use for quantitative monitoring of solid-phase organic synthesis. Other reports have also indicated the value of using 19 F NMR spectroscopy to study reactions performed on solid support [19][20][21][22] or for identification of members in libraries encoded with fluorinated tags.…”

Section: Introductionmentioning

confidence: 98%

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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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“…Resin-Bound 3-Fluoro-4-(hydroxymethyl)phenoxyacetic Acid (17). DIC (99 µL, 0.64 mmol) was added to an ice-cold solution of pentafluorophenol (187 mg, 1.00 mmol) in EtOAc (5 mL).…”

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

confidence: 99%

Section: Introductionmentioning

confidence: 98%

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

2000

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“…19 F-NMR of nine aryl fluoride tags has been used to analyse combinatorial libraries [ 105 , 106 ]. Kihlberg et al introduced three aryl fluoride tags in an earlier report [ 115 ]. Other analysis methods are enumerated in Table 5 .…”

Section: Analysis Methodsmentioning

confidence: 99%

Solid-Phase Synthesis of N-Substituted Glycine Oligomers (α‑Peptoids) and Derivatives

2010

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Peptoids (N-substituted polyglycines and extended peptoids with variant backbone amino-acid monomer units) are oligomeric synthetic polymers that are becoming a valuable molecular tool in the biosciences. Of particular interest are their applications to the exploration of peptoid secondary structures and drug design. Major advantages of peptoids as research and pharmaceutical tools include the ease and economy of synthesis, highly variable backbone and side-chain chemistry possibilities. At the same time, peptoids have been demonstrated as highly active in biological systems while resistant to proteolytic decay. This review with 227 references considers the solid-phase synthetic aspects of peptoid preparation and utilization up to 2010 from the instigation, by R. N. Zuckermann et al., of peptoid chemistry in 1992.

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“…S N 2 reactions between amines and alkyl halides on solid phase are most frequently performed after introduction of the halide as halogenated carboxylic acids. [175][176][177][178][179][180][181][182][183][184][185][186] An elegant example of this strategy is the automated submonomer SPS of peptoids developed by Zuckermann et al in the early 1990s that provided 63-90% yields. 175 This method, outlined in Scheme 16, was recently extended with respect to the tolerance of functionalities present in the amine building blocks (76-92% yields).…”

Section: Halogen Displacementmentioning

confidence: 99%

N-Alkylation Reactions and Indirect Formation of Amino Functionalities in Solid-Phase Synthesis

Olsen¹,

Franzyk²,

Jaroszewski³

2005

Synthesis

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Aliphatic and aromatic amino functionalities are present in a wide variety of natural products and drugs, as well as in synthetic small molecular probes with therapeutic and/or diagnostic potential in drug discovery. As solid-phase synthesis and combinatorial chemistry have emerged as important tools for generation of compound libraries, development of broad-scope and efficient chemistry for the introduction of various functional groups into resinanchored substrates is highly important. Herein, we present a review of the literature concerning formation of the amino functionality on solid phase.

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Fluorinated linkers for monitoring solid-phase synthesis using gel-phase 19F NMR spectroscopy

Cited by 35 publications

References 5 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

Solid-Phase Synthesis of N-Substituted Glycine Oligomers (α‑Peptoids) and Derivatives

N-Alkylation Reactions and Indirect Formation of Amino Functionalities in Solid-Phase Synthesis

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Fluorinated linkers for monitoring solid-phase synthesis using gel-phase 19F NMR spectroscopy

Cited by 35 publications

References 5 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

Solid-Phase Synthesis of N-Substituted Glycine Oligomers (α‑Peptoids) and Derivatives

N-Alkylation Reactions and Indirect Formation of Amino Functionalities in Solid-Phase Synthesis

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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