quantitative analysis of combinatorial libraries in Visual Studio .NET

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quantitative analysis of combinatorial libraries
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Figure 9.20. Compound A prepared on TentaGel resin with a photolinkage.
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To illustrate these principles, compound A in Figure 9.20 was prepared on TentaGel resin with a photolinkage.24,51 The resin was characterized by quantitative solid-phase NMR, traditional elemental analysis, and solids CLND. By NMR the loading was 0.38 mmole/g while the CHN analysis showed 0.34 mmole/g, and the solids CLND showed 0.40 mmole/g. While not strictly relevant to the cleavage question, the solids CLND is a convenient, high-throughput way to characterize solid-phase synthesis samples. The photolytic cleavage of this compound was measured using direct inject CLND. A weighed sample of the resin (3 5 mg) was placed in a small glass vial and slurried with 200 mL of solvent. The sealed vial was then exposed to 10 mW/cm2 light energy, measured at 360 nm.24 After an appropriate time, the vial was removed from the photolysis and diluted for analysis. We have previously shown that the DI-CLND is sensitive to solvent and must be calibrated with the standards dissolved in the same solvent as the samples are dissolved in. The time course for cleavage of the compound in four different solvents is shown in Figure 9.21. 9.4.2. Quantitative Analysis by Standard Bead LC/MS Method
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It is very useful to quantitatively determine the amounts of compound released from single beads. The CLND, ELSD, and NMR methods are not applicable for the subnanomole amounts of sample released from single beads, so these measurements will need the more sensitive UV or MS detectors. For single compounds an LC/MS run in selected ion mode is an extremely sensitive and speci c analytical method. To conduct our quantitative LC/MS single-bead analysis, we developed a so-called standard bead LC/MS method.52 A standard set of compounds with different cLogP s was selected. They are Mono-Fmoc-Lysine, BisCbz-Lysine, Fmoc-Cbz-Lysine, and Bis-Fmoc-Lysine. All compounds were synthesized on both TentaGel beads with the Affymax photo-cleavage linker and Wang acid-cleavable linker. The cLogP varied from 0.9 to 7.2, representing the cLogP diversity of common split/pool libraries. The standard compounds were simple and commercially available (Advanced
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characterization of split-pool encoded combinatorial libraries
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DMSO+0.5%TFA Solvent(s)
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Figure 9.21. Time course for cleavage of compound A from resin in four solvents.
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ChemTech, Louisville, KY). Figure 9.22 shows the molecular structures of the standard compounds. The standard bead synthetic procedure is summarized in Figure 9.23. ABI 433 Amino Acid Synthesizer was used to synthesize all compounds on both TentaGel beads with the Affymax photo-cleavage linker and Wang acid-cleavable linker. First, the TentaGel photolinker or Wang resin was washed with dichloromethane (DCM) and N-methylpyrrolidone (NMP). Then 4 equiv (relative to the resin) of R1-R2-Lys-OH, 4 equiv of N,Ndicyclohexylcarbodiimide, and 4 equiv of 1-hydroxybenzotriazole anhydrous in NMP were added to the resin, where R1 is Fmoc or Cbz, and R2 is Boc, Cbz or Fmoc. The reaction mixture was gently shaken for 2 hours at room temperature, and then washed with NMP and DCM 6 times. The resin was lyophilized for 2 days. For mono-Fmoc-Lysine, Boc was removed with TFA after the coupling of Fmoc-Lys-OH was done. After synthesis and drying, the standard beads were ready for use. Single beads were picked into individual tapered glass microvials. For the beads with the Affymax photo-cleavage linker, 25 mL mixture of 75% IPA, 25% DMSO, and 0.3% TFA was added to a single bead, and the microvial was sealed. The vial was placed on an orbital shaker and irradiated with 360 nm
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quantitative analysis of combinatorial libraries
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clogp=0.9 MW = 368.4 Mono-Fmoc-Lys
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clogp=3.1 MW = 414.5 Bis-CBZ-Lys
clogp=5.4 MW = 502.6 Fmoc-CBZ-Lys
clogp=7.2 MW = 590.8 Bis-Fmoc-Lys
Figure 9.22. Structures and mass spectra of the standard compounds with different cLogPs.
OH O Tentagel Wang
N,N-Dicyclohexylcarbodiimide(DCC) OH in N-Methylpyrrolidone (NMP) O
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Tentagel Photolinker
Boc removed with TFA after the coupling of Fmoc-Lys-OH was done
R1 Fmoc CBz Fmoc Fmoc R2 Boc CBz CBz Fmoc
Fmoc-Lys-OH Bis-CBz-Lys-OH Fmoc-CBz-Lys-OH Bis-Fmoc-Lys-OH
Figure 9.23. Synthetic scheme of standard compounds.
UV, 10 mW/cm2, for 2 hours. The sample was then ready for LC/MS analysis. For the beads with the Wang acid-cleavable linker, 50 mL of 95% TFA was added to a single bead, and the microvial was left at room temperature for 1 hour to cleave the compound. After evaporating the TFA, 25 mL of ACN was added into the bead vial. The whole sample cleaved from a single