f nmr as a tool for encoding libraries in .NET framework

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Scheme 2.10. Reagents and conditions: (i) NaH, DMF, 60 C, 3 h, then rt for 16 h.
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Scheme 2.11. Reagents and conditions: (i) SnCl4 (10 equiv.), chloroform, H20, 30 C, 1.5 4 h.
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various time points and then treated with excess 4- uorophenolate. The 19F NMR analysis determined the rate of formation of the Merri eld ether. The rate of the cleavage reaction was studied for the two Merri eld ethers 25 and 26 using 19F NMR spectroscopy (Scheme 2.11). A 1.5-fold excess of stannic chloride was added to each resin sample, 25 and 26, suspended in d-chloroform, and the increase in the intensities of the 19F signals at -142 and -124 ppm, due to the cleaved products, respectively, were monitored over some time.
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F NMR AS A TOOL FOR ENCODING LIBRARIES
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F NMR is an excellent tool for generating the encoding method for single beads in combinatorial libraries produced by the mix and split synthetic method. The same advantages of using 19F NMR spectroscopy to monitor reactions are true for using 19F NMR as a tool for encoding libraries. Numerous uorine tags including many from commercially available sources are available for use. The relative stability of the uorine tag is also an impor-
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reaction monitoring and quanti cation of resin loading
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tant positive characteristic. Due to the wide range of chemical shifts observed for uorinated molecules, even library compounds that contain a uorine atom usually display a chemical shift different from any encoding tags used. This characteristic usually distinguishes the library compound from the tag. Also in most cases the library compound is cleaved from the resin before encoding so that overlap of the 19F signal does not become an issue. A recent report20 uses a uorine encoding method for the rst position monomers in a mix and split library to assist in the mass spectral deconvolution of library hits. Mass spectroscopy is used as the primary structural deconvolution tool. However, due to mass redundancies in the screened pools, mass spectral analysis alone cannot unequivocally determine the structure of the hits. Thus, to avoid having to re-synthesize numerous compounds, 19F encoding is used to provide additional structural information. A hybrid structural determination strategy is employed that relies on mass spectral analysis of the active bead coupled with on-bead analysis of the rst position nonreleasable code. This strategy reduces the number of structural possibilities to a single structure in every case. In practice, a series of commercially available uorine carboxylic acids are used to generate an encoding system for mix and split libraries. The tags are attached to the resin via an amide bond, and each tag displays a unique distinguishable uorine chemical shift. A large number of codes may be generated from a small set of differentiable uorine carboxylic acid tags. Combinations of two uorine tags are used at a time, along with 50 to 100 rst-position encoded resin pools that require 11 to 15 individual tags. The large batches of encoded resin are synthesized as outlined in Scheme 2.12.
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Scheme 2.12. Synthesis of bulk F recoded resin. Reagents and conditions: (i) N-Boc-e-NFmoc-Lys-OH, DIC, HOBt, DCM; (ii) piperidine, DCM; (iii) F-tags-COOH, DIC, HOBt, DCM.
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f nmr as a tool for encoding libraries
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Figure 2.6. Decoding of a combinatorial chemistry library bead by F NMR.
A typical synthesis of a combinatorial mix and split library proceeds by rst de ning the required resin pools, followed by deprotection of the aamine position, attachment of the appropriate linker, and then attachment of the library core and subsequent derivatization following a typical mix and split protocol. Deconvolution of the active bead proceeds by acquiring the 19F NMR spectra of the bead. These investigations used an NMR equipped with a magic angle spinning probe. It took one to four hours to read the 19F code from a single bead for a typical sample using 130 mm aminomethyl polystyrene resin with a library and tag loading capacity of 1.2 mmol/g each. Single-bead spectra of library hits are compared to known spectra of coded resin batches shown in Figure 2.6. Another recent report21,22 uses a set of chemically robust aryl uorides as molecular tags. These molecules exhibit chemical shifts that range from -55 to -25 ppm relative to uorobenzene, and are tolerant to a wide variety of chemical transformations in solid-phase chemistry. Poly-N-alkylglycines were chosen as a model system for the preparation of combinatorial