NMR methods in combinatorial chemistry

Current Opinion in Chemical Biology

Volumn 2, Issue 3, 1998, Pages 372-375

  Shapiro, Michael J ^a   Wareing, James R ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; PLANT RESIN;

HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; ORGANIC CHEMISTRY; REVIEW; SOLUTION AND SOLUBILITY;

CHEMISTRY, ORGANIC; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; INDICATORS AND REAGENTS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; RESINS, PLANT; SOLUTIONS;

EID: 0032084292     PISSN: 13675931     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1367-5931(98)80011-2     Document Type: Article

References (36)

1. Manatt SL, Amsden SF, Bettison CA, Frazer WT, Gudman JT, Lenk BE, Lubetich JF, McNelly EA, Smith SC, Templeton DJ, Pinnell RP: A fluorine-19 NMR approach for studying merrifield solid-phase peptide synthesis. Tetrahedron Lett 1980, 21:1397-1400.
2. 19F NMR spectroscopy to evaluate reactions in solid phase organic synthesis. Tetrahedron Lett 1996, 37:7649-7652.
3. 15N NMR. Tetrahedron Lett 1997, 38:8643-8646.
4. Meissner A, Bloch P, Humpfer E, Spraul M, Sorensen OWL: Reduction of inhomogeneous line broadening in two dimensional high-resolution MAS NMR spectra of molecules attached to swelled resins in solid-phase synthesis. J Am Chem Soc 1997, 119:1787-1788.
5. Shapiro MJ, Chin J, Marti RE, Jarosinski MA: Enhanced resolution in MAS NMR for combinatorial chemistry. Tetrahedron Lett 1997, 38:1333-1336.
6. Chin J, Fell B, Pochapsky S, Shapiro MJ, Wareing JR: 2D SECSY NMR for combinatorial chemistry. High resolution MAS spectra for resin-bound molecules. J Org Chem 1998, 63:1309-1311.
7. Chili E, Oliveira E, Marchetto R, Nakaie CR; Correlation between solvation of peptide resins and solvent properties. J Org Chem 1996, 61:8992-9000. A good description of the swelling properties of resins. Potentially very useful in designing reactions in combinatorial chemistry.
8. 1H NMR spectra of solid-phase-synthesis resins. J Org Chem 1996, 61:1558-1559.
9. Dhalluin CF, Boutillon C, Tartar AL, Lippens G: Magic angle spinning NMR in solid phase synthesis. J Am Chem Soc 1997, 119:10494-10500. An excellent application of the utility of magic angle spinning (MAS) NMR to monitoring peptide synthesis. Important observations concerning the quality of MAS NMR and the reactivity of the peptide are presented. At critical synthesis steps, the MAS NMR gave information concerning aggregation and coupling abilities.
10. Pop IE, Dhalluin CF, Deprez BP, Melnyk PC, Lippens GM, Tartar AL: Monitoring of a three-step solid phase synthesis involving a heck reaction using magic angle spinning NMR spectroscopy. Tetrahedron 1996, 52:12209-12222.
11. Jelinek R, Valente AP, Valentine KG, Opalla SJ: Two dimensional NMR spectroscopy of peptides on beads. J Magn Reson 1997, 125:185-187.
12. Mass WE, Laukien FH , Cory DG: Gradient, high resolution, magic angle sample spinning NMR. J Am Chem Soc 1996, 118:13035-13086.
13. 1H MAS NMR investigations on single macro beads in the suspended state. Angew Chem Int Ed 1996, 35:2867-2869.
14. Sarkar S, Garigipati RS, Adams JL, Keifer PA: An NMR method to identify nondestructively chemical compounds bound to a single solid-phase-synthesis bead for combinatorial chemistry applications. J Am Chem Soc 1996, 118:2305-2306.
15. Chin J, Fell B, Shapiro MJ, Tomesh J, Wareing JR, Bray AM: Magic angle spinning NMR for reaction monitoring and structure determination of molecules attached to multipin crowns. J Org Chem 1997, 62:538-539. The first example of magic angle spinning NMR on crowns is presented. The ability to monitor a reaction on crown and confirm the structure of the reaction product without resorting to cleavage is demonstrated and should ehance the use of this convinient format.
16. Lindon JC, Nicholson JK, Wilson ID: Direct coupling of chromatographic separations to NMR spectroscopy. Prog NMR Spectrosc 1996, 29:1-49.
17. Lindon JC, Farrant RD, Sanderson PN, Doyle PM, Goughg SL, Spraul M, Hoffman M, Nicholson JK: Separation and characterization of components of peptide libraries using on-flow coupled HPLC-NMR spectroscopy. Magn Reson Chem 1995, 33:857-863.
18. Chin J, Fell JB, Jarosinski M, Shapiro MJ, Wareing JR: HPLC/NMR in combinatorial chemistry. J Org Chem 1998, 63:386-390.
19. Olson DL, Peck TL, Webb AG, Sweedler JV: On-Line NMR detection for capillary electrophoresis applied to peptide analysis. Peptides: Chem Struct Biol 1996, 730-731. NMR on nanograms of material-who needs mass spectrometry?!
20. Egner BJ, Bradley M: Analytical techniques for solid-phase organic combinatorial chemistry. Drug Discov Today 1997, 3:102-109.
21. Burton KI, Everett JR, Newman MJ, Pullen FS, Richards DS, Swanson AG: On-line liquid chromatography coupled with high field NMR and mass spectrometry (LC-NMR-MS); a new technique for drug metabolism structure determination. J Pharm Biomed Anal 1997, 15:1903-1912. The first practical examplo of the coupling of high performance liquid chromatography, nuclear magnetic resonance and mass spectrometry in a tandom sequence. Although the application deals with a drug metabolism problem, the extension to combinatorial chemistry is obvious. Watch out for commercialized versions of this intriguing system soon.
22. 1H NMR spectroscopy in the nanoliter scale. Anal Chem 1996, 68:1110-1115.
23. Dalvit C, Bohlen JM: Multiple-solvent suppression in double-quantum NMR experiments with magic angle pulsed field gradients. Magn Reson Chem 1996, 34:829-833.
24. Shuker SB, Hajduk PJ, Meadows RP, Fesik SW: Discovering high-affinity ligands for proteins: SAR by NMR. Science 1996, 274:1531-1534.
25. Kessler H: Structure activity relationships by NMR, A new procedure for drug discovery by a combinatorial-rational approach. Angew Chem Int Ed 1997, 36:829-831.
26. Hajduk PJ, Sheppard G, Nettesheim DG, Olejiniczak ET, Shukar SB, Meadows RP, Steinman DH, Carrera GM, Marcotte PA, Severin J et al.: Discovery of potent non-peptide inhibitors of stromelysin using SAR by NMR. J Am Chem Soc 1997, 119:5818-5827. The first practical utilization of the structure- activity relationship by NMR technique to design active inhibitors of stromelysin. Two small molecular fragments were found and then linked. The optimization of the synthetic effort took only six months.
27. Morris KF, Johnson CS Jr: Diffusion-ordered two-dimensional nuclear magnetic resonance spectroscopy. J Am Chem Soc 1992, 114:3139-3141.
28. Waldeck AR, Kuchel PW, Lennon AJ, Chapman BE: NMR diffusion measurements to characterise membrane transport and solute binding. Prog NMR Spectrosc 1997, 30:39-68. An excellent review article on the description of the theory and utility of pulse field gradient-based NMR experiments.
29. Lin M, Shapiro MJ, Wareing JR: Diffusion-edited NMR-affinity NMR for direct observation of molecular interactions. J Am Chem Soc 1997, 119:5249-5250. The first paper to deal with the NMR spectral editing of a mixture by pulse field gradient to observe bound ligands. The experiment has been termed 'affinity NMR'.
30. Shapiro M, Lin M: Mixture analysis in combinatorial chemistry. Application of diffusion-resolved NMR spectroscopy. J Org Chem 1996, 61:7617-7619.
31. Lin M, Shapiro MJ, Wareing JR: Screening mixtures by affinity NMR. J Org Chem 1997, 62:8930-8931.
32. Hajduk, PJ, Olejniczak, ET, Fesik FW: Application of PFG diffusion NMR and spin echo NMR to identify ligands that bind to macromolecules FKBP and stromelysin. J Am Chem Soc 1997, 119:12257-12261. Using a subtraction scheme, the background NMR signals arising from the biomolecule are eliminated allowing the direct observation of the spectrum of the bound ligand.
33. Jerschow A, Muller N: 3D diffusion-ordered TOCSY for slowly diffusing molecules. J Magn Res A 1996, 123:222-225.
34. Gafni A, Cohen Y: Complexes of macrocycles with γ-cyclodextran as deduced from NMR diffusion measurements. J Org Chem 1997, 62:120-125.
35. Ponsting H, Otting G: Detection of protein-ligand NOEs with small, weakly binding ligands by combined relaxation and diffusion filtering. J Biol NMR 1997, 9:441-444.
36. Meyer B, Weimar T, Peters T: Screening mixtures for biological activity by NMR. Eur J Biochem 1997, 246:705-709. Biologically active compounds are screened from a mixture using the transfer nuclear Overhauser spectroscopy (NOE) experiment. In addition, the NOEs from the binding molecule may allow its bioactive conformation to be determined.