Analytical methods for the monitoring of solid phase organic synthesis

Il Farmaco - Tập 57 - Trang 497-510 - 2002
M Dal Cin1, S Davalli1, C Marchioro1, M Passarini1, O Perini1, S Provera1, A Zaramella1
1Computational, Analytical and Structural Sciences, GlaxoSmithKline Medicines Research Center, Via Fleming 4, 37135 Verona, Italy

Tài liệu tham khảo

Barany, 1979 Thompson, 1996, Chem. Rev., 96, 555, 10.1021/cr9402081 Gordon, 1994, Applications of combinatorial technologies to drug discovery. 1. Combinatorial synthesis, library screening strategies and future directions, J. Med. Chem., 37, 1385, 10.1021/jm00036a001 Egner, 1997, Analytical techniques for solid-phase organic and combinatorial synthesis, Drug Discov. Today, 2, 102, 10.1016/S1359-6446(97)01003-9 Keifer, 1998, New methods for obtaining high-resolution NMR spectra of solid-phase synthesis resins, natural products, and solution-state combinatorial chemistry libraries, Drugs Future, 23, 301, 10.1358/dof.1998.023.03.858431 Fitch, 1999, Analytical methods for quality control of combinatorial libraries, Annu. Rep. Comb. Chem. Mol. Divers., 2, 33, 10.1007/978-94-017-0735-0_5 Gallop, 1997, New methods for analyzing compounds on polymeric supports, Curr. Opin. Chem. Biol., 1, 94, 10.1016/S1367-5931(97)80114-7 Shapiro, 1999, NMR methods utilized in combinatorial chemistry research, Prog. Nucl. Magn. Reson. Spectrosc., 35, 153, 10.1016/S0079-6565(99)00008-4 Keifer, 2000, NMR spectroscopy in drug discovery: tools for combinatorial chemistry, natural products and metabolism research, Prog. Drug Res., 55, 137, 10.1007/978-3-0348-8385-6_5 Enjalbal, 2000, Mass spectrometry in combinatorial chemistry, Mass Spectrom. Rev., 19, 139, 10.1002/1098-2787(200005/06)19:3<139::AID-MAS2>3.0.CO;2-S Gremlinch, 1999, The use of optical spectroscopy in combinatorial chemistry, Biotechnol. Bioeng., 61, 179, 10.1002/(SICI)1097-0290(1998)61:3<179::AID-CC5>3.0.CO;2-0 Kaiser, 1970, Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides, Anal. Biochem., 34, 595, 10.1016/0003-2697(70)90146-6 Flegel, 1990, A sensitive, general method for quantitative monitoring of continuous flow solid phase peptide synthesis, J. Chem. Soc., Chem. Commun., 7, 536, 10.1039/c39900000536 Virgilio, 1994, Simultaneous solid-phase synthesis of β-turn mimetics incorporating side-chain functionality, J. Am. Chem. Soc., 116, 11580, 10.1021/ja00104a053 Hermkens, 1997, Solid-phase organic reactions. II: a review of the literature Nov 95–Nov 96, Tetrahedron, 53, 5643, 10.1016/S0040-4020(97)00279-2 Booth, 1998, Solid-phase organic reactions. III. A review of the literature Nov 96–Dec 97, Tetrahedron, 54, 15385, 10.1016/S0040-4020(98)00968-5 Hall, 1999, Recent advances in solid-phase synthesis, Annu. Rep. Comb. Chem. Mol. Divers., 2, 15, 10.1007/978-94-017-0735-0_3 Gordeev, 1996, Approaches to combinatorial synthesis of heterocycles: a solid-phase synthesis of 1,4-dihydropyridines, J. Org. Chem., 61, 924, 10.1021/jo951706s Erb, 1992, Versatile approach to encoding combinatorial organic syntheses using chemically robust secondary amine tag, Proc. Natl. Acad. Sci. USA, 91, 11422, 10.1073/pnas.91.24.11422 Brenner, 1992, Proc. Natl. Acad. Sci. USA, 89, 5381, 10.1073/pnas.89.12.5381 Nestler, 1994, A general method for molecular tagging of encoded combinatorial chemistry libraries, J. Org. Chem., 59, 4723, 10.1021/jo00096a008 Ni, 1996, Encoded combinatorial chemistry: binary coding using chemically robust secondary amine tags, Methods Enzymol., 267, 261, 10.1016/S0076-6879(96)67018-9 Nicolaou, 1995, Radiofrequency encoded combinatorial chemistry, Angew. Chem., Int. Ed. Engl., 34, 2289, 10.1002/anie.199522891 Ni, 1996, Versatile approach to encoding combinatorial organic syntheses using chemically robust secondary amine tags, J. Med. Chem., 39, 1601, 10.1021/jm960043j Needels, 1998, 339 Geysen, 1996, Isotope or mass encoding of combinatorial libraries, Chem. Biol., 3, 679, 10.1016/S1074-5521(96)90136-2 Carrasco, 1997, Direct monitoring of organic reactions on polymeric supports, Tetrahedron Lett., 40, 2407 Murray, 1999, Rapid reaction scanning of solid phase chemistry using resins incorporating analytical constructs, Tetrahedron Lett., 40, 5609, 10.1016/S0040-4039(99)01042-4 Zaramella, 2001, Dansyl and dabsyl analytical constructs as tools for the accurate estimation of compounds in solid-phase synthesis, J. Comb. Chem., 3, 410, 10.1021/cc0001147 Smallcombe, 1995, WET solvent suppression and its applications to LC NMR and high-resolution NMR spectroscopy, J. Magn. Reson., 117, 295, 10.1006/jmra.1995.0759 S.L. Patt, Single- and multiple-frequency-shifted laminar pulses, J. Magn. Reson. 96 (1992) 94–102. Look, 1994, Methods for combinatorial organic synthesis: the use of fast 13C NMR analysis for gel phase reaction monitoring, J. Org. Chem., 59, 7588, 10.1021/jo00104a010 Gordeev, 1996, Approaches to combinatorial synthesis of heterocycles. A solid phase synthesis of 1,4-dihydropyridines, J. Org. Chem., 61, 924, 10.1021/jo951706s Gordeev, 1996, Approaches to combinatorial synthesis of heterocycles. Solid phase synthesis of pyridines and pyrido[2,3-d]-pyrimidines, Tetrahedron Lett., 37, 4643, 10.1016/0040-4039(96)00923-9 Salvino, 2001, Synthesis of a new fluoro-wang resin for solid-phase reaction monitoring by 19F NMR spectroscopy, J. Comb. Chem., 3, 177, 10.1021/cc000076r Svensson, 2000, Preparation of fluorinated linkers: use of 19F NMR spectroscopy to establish conditions for solid-phase synthesis of pilicide libraries, J. Comb. Chem., 2, 736, 10.1021/cc0000646 Hochlowsky, 1999, Encoding of combinatorial chemistry libraries by fluorine-19 NMR, J. Comb. Chem., 1, 291, 10.1021/cc9900145 Shapiro, 1996, 19F NMR monitoring of a SNAr reaction on solid support, Tetrahedron Lett., 37, 4671, 10.1016/0040-4039(96)00960-4 Johnson, 1995, Solid-phase synthesis of alkenes using the Horner–Wadsworth–Emmons reaction and monitoring by gel-phase 31P NMR, Tetrahedron Lett., 36, 9253, 10.1016/0040-4039(95)02017-J Fitch, 1994, High-resolution 1H NMR in solid-phase organic synthesis, J. Org. Chem., 59, 7955, 10.1021/jo00105a006 Keifer, 1996, A comparison of NMR spectra obtained for solid phase synthesis resins using conventional high-resolution, magic-angle-spinning, and high-resolution magic-angle-spinning probes, J. Magn. Reson., Ser. A, 119, 65, 10.1006/jmra.1996.0052 Warras, 2000, Quantitative monitoring of solid-phase organic reactions by high-resolution magic angle spinning NMR spectroscopy, J. Org. Chem., 65, 2946, 10.1021/jo9914824 Lippens, 2000, High resolution magic angle spinning NMR in combinatorial chemistry, Actual Chim., 9, 21 Keifer, 1996, The influence of resin structure, tether length, and solvent upon the high-resolution 1H NMR spectra of solid-phase-synthesis resins, J. Org. Chem., 61, 1558, 10.1021/jo952001t Gariparati, 1996, Use of spin echo magic angle spinning 1H NMR in reaction monitoring in combinatorial organic synthesis, J. Org. Chem., 61, 2911, 10.1021/jo952153o Wehler, 1996, Magic angle spinning NMR: a valuable tool for monitoring the progression of reactions in solid phase synthesis, Tetrahedron Lett., 37, 4771, 10.1016/0040-4039(96)00931-8 Shapiro, 1997, Enhanced resolution in MAS NMR for combinatorial chemistry, Tetrahedron Lett., 38, 1333, 10.1016/S0040-4039(97)00092-0 Meissner, 1997, Reduction of inhomogeneous line broadening in two-dimensional high-resolution MAS NMR of molecules attached to welled resins in solid-phase synthesis, J. Am. Chem. Soc., 119, 1787, 10.1021/ja9630001 Mass, 1996, Gradient, high resolution, magic angle sample spinning NMR, J. Am. Chem. Soc., 118, 13085, 10.1021/ja962227t Yan, 1999, A comparison of various FTIR and FT Raman methods: applications in the reaction optimization stage of combinatorial chemistry, J. Comb. Chem., 1, 46, 10.1021/cc980003w Yan, 1997, Monitoring the progression of organic reactions on solid supports, Recent Res. Dev. Org. Chem., 1, 55 Yan, 1999, Role of Fourier transform Infrared Spectroscopy in the rehearsal phase of combinatorial chemistry: a thin-layer chromatography equivalent for on-support monitoring of solid-phase organic synthesis, J. Chromatogr. B: Biomed. Sci. Appl., 725, 91, 10.1016/S0378-4347(98)00505-2 Rahman, 1998, Infrared and Raman spectra of a single resin bead for analysis of solid-phase reactions and use in encoding combinatorial libraries, J. Org. Chem., 63, 6196, 10.1021/jo980258w Gremlich, 1994, B5, 429 Huber, 1999, Monitoring solid phase synthesis by infrared spectroscopic techniques, Anal. Chim. Acta, 393, 213, 10.1016/S0003-2670(98)00770-3 Pivonka, 1997, Tools for combinatorial chemistry: real-time single-bead infrared analysis of a resin-bound photocleavage reaction, Anal. Chem., 69, 3851, 10.1021/ac9700843 Russell, 1996, Analytical techniques for combinatorial chemistry: quantitative infrared spectroscopic measurements of deuterium labelled protecting group, J. Am. Chem. Soc., 118, 7941, 10.1021/ja960838f Gosselin, 1996, Photoacustic FTRI spectroscopy, a nondestructive method for sensitive analysis of solid-phase organic chemistry, J. Org. Chem., 61, 7980, 10.1021/jo961393g Pivonka, 2000, Implementation of Raman spectroscopy as an analytical tool throughout the synthesis of solid-phase scaffolds, Appl. Spectrosc., 54, 1584, 10.1366/0003702001948835