Quantitative electrospray mass spectrometry for the rapid assay of enzyme inhibitors

Boyce, 1994, Peptidosteroidal receptors for opioid peptides — sequence-selective binding using a synthetic receptor library, J. Am. Chem. Soc., 116, 7955, 10.1021/ja00096a086 Gallop, 1994, Application of combinatorial technologies to drug discovery. 1. Background and peptide combinatorial libraries, J. Med. Chem., 37, 1233, 10.1021/jm00035a001 Kurth, 1994, Library-based lead compound discovery — antioxidants by an analogous synthesis deconvolutive assay strategy, J. Org. Chem., 59, 5862, 10.1021/jo00099a008 Nestler, 1994, A general method for molecular tagging of encoded combinatorial chemistry libraries, J. Org. Chem., 59, 4723, 10.1021/jo00096a008 Gold, 1995, Diversity of oligonucleotide functions, Annu. Rev. Biochem., 64, 763, 10.1146/annurev.bi.64.070195.003555 Liu, 1995, A general solid-phase synthesis strategy for the preparation of 2-pyrrolidinemethanol ligands, J. Org. Chem., 60, 7712, 10.1021/jo00129a002 Pinilla, 1995, A review of the utility of soluble peptide combinatorial libraries, Biopolymers, 37, 221, 10.1002/bip.360370306 Francis, 1996, Combinatorial approach to the discovery of novel coordination complexes, J. Am. Chem. Soc., 118, 8983, 10.1021/ja961842u Stevens, 1996, Non nucleic acid inhibitors of protein-DNA interactions identified through combinatorial chemistry, J. Am. Chem. Soc., 118, 10650, 10.1021/ja962452a Thompson, 1996, Synthesis and applications of small molecule libraries, Chem. Rev., 96, 555, 10.1021/cr9402081 Liang, 1996, Parallel synthesis and screening of a solid phase carbohydrate library, Science, 274, 1520, 10.1126/science.274.5292.1520 Georgiou, 1997, Display of heterologous proteins on the surface of microorganisms: from the screening of combinatorial libraries to live recombinant vaccines, Nature Biotechnol., 15, 29, 10.1038/nbt0197-29 Chu, 1995, Affinity capillary electrophoresis, Acc. Chem. Res., 28, 461, 10.1021/ar00059a004 Chu, 1996, Affinity capillary electrophoresis mass spectrometry for screening combinatorial libraries, J. Am. Chem. Soc., 118, 7827, 10.1021/ja960213h Cheng, 1995, Using electrospray ionization FTICR mass spectrometry to study competitive binding of inhibitors to carbonic anhydrase, J. Am. Chem. Soc., 117, 8859, 10.1021/ja00139a023 Youngquist, 1995, Generation and screening of combinatorial peptide libraries designed for rapid sequencing by mass spectrometry, J. Am. Chem. Soc., 117, 3900, 10.1021/ja00119a002 Boutin, 1996, Combinatorial peptide libraries: robotic synthesis and analysis by NMR, mass spectrometry, tandem mass spectrometry and high-performance capillary electrophoresis techniques, Anal. Biochem., 234, 126, 10.1006/abio.1996.0064 Gao, 1996, Screening derivatized peptide libraries for tight binding inhibitors to carbonic anhydrase II by electrospray ionization-mass spectrometry, J Med. Chem., 39, 1949, 10.1021/jm960013g Kupke, 1995, Oxidative decarboxylation of peptides catalyzed by flavoprotein EpiD. Determination of substrate specificity using peptide libraries and neutral loss mass spectrometry, J. Biol. Chem., 270, 11282, 10.1074/jbc.270.19.11282 Berlin, 1997, Spectrometrically monitored selection experiments: quantitative laser desorption mass spectrometry of small chemical libraries, Chem. Biol., 4, 63, 10.1016/S1074-5521(97)90237-4 Wu, 1997, An automated MALDI mass spectrometry approach for optimizing cyclosporin extraction and quantitation, Anal. Chem., 10.1021/ac970276y Lee, 1989, Real-time reaction monitoring by continuous-introduction ion-spray tandem mass spectrometry, J. Am. Chem. Soc., 111, 4600, 10.1021/ja00195a012 Henion, 1994, Quantitative capillary electrophoresis ion spray mass spectrometry on a benchtop ion trap for the determination of isoquinoline alkaloids, Anal. Chem., 66, 2103, 10.1021/ac00085a028 Hegy, 1996, High throughput electrospray mass spectrometry of combinatorial chemistry racks with automated contamination surveillance and results reporting, Rapid Commun. Mass Spectrom., 10, 1894, 10.1002/(SICI)1097-0231(199612)10:15<1894::AID-RCM708>3.0.CO;2-2 Siuzdak, 1996 Varki, 1993, Biological roles of oligosaccharides — all theories are correct, Glycobiology, 3, 97, 10.1093/glycob/3.2.97 Vaghefi, 1987, Synthesis of glycopyranosylphosphonate analogs of certain natural nucleoside diphosphate sugars as potential inhibitors of glycosyltransferases, J. Med. Chem., 30, 1383, 10.1021/jm00391a020 Vaghefi, 1987, Synthesis of certain nucleoside methylenediphosphonate sugars as potential inhibitors of glycosyltransferases, J. Med. Chem., 30, 1391, 10.1021/jm00391a021 Palcic, 1989, A bisubstrate analog inhibitor for α-(1,2)-fucosyltransferase, J. Biol. Chem., 264, 17174, 10.1016/S0021-9258(18)71475-0 Hindsgaul, 1991, Evaluation of deoxygenated oligosaccharide acceptor analogs as specific inhibitors of glycosyltransferases, J. Biol. Chem., 266, 17858, 10.1016/S0021-9258(18)55207-8 Lowary, 1994, Recognition of synthetic O-methyl, epimeric, and amino analogues of the acceptor alphaL-FUCP-(1,2)-beta-D-GALP-OR by the blood-group A and B gene specified glycosyltransferases, Carbohydr. Res., 251, 33, 10.1016/0008-6215(94)84275-2 Endo, 1996, Novel aspects of interactions between UDP-Gal and GIcNAc β-1,4galactosyltransferase: transferability and remarkable inhibitory activity of UDP-(mono-O-methylated gal), UDP-fuc and UDP-man, Bioorg. Med. Chem., 4, 1939, 10.1016/S0968-0896(96)00176-9 Oiao, 1996, Synergistic inhibition of human alpha- 1,3-fucosyltransferase V, J. Am. Chem. Soc, 118, 7653, 10.1021/ja960274f Hayashi, 1997, A chemoenzymatic synthesis of UDP-(2-deoxy-2-fluoro)-galactose and evaluation of its interaction with galactosyltransferase, Bioorg. Med. Chem., 5, 497, 10.1016/S0968-0896(96)00263-5 Murray, 1997, Mechanism of human alpha-1,3-fucosyltransferase V: glycosidic cleavage occurs prior to nucleophilic attack, Biochemistry, 36, 823, 10.1021/bi962284z Wang, 1997, A search for pyrophosphate mimics for the development of substrates and inhibitors of glycosyltransferases, Bioorg. Med. Chem., 5, 661, 10.1016/S0968-0896(97)00005-9 Ichikawa, 1992, Chemical-enzymatic synthesis and conformational analysis of sialyl lewis X and derivatives, J. Am. Chem. Soc., 114, 9283, 10.1021/ja00050a007 Paulson, 1983, Glycoproteins: what are the sugar chains for?, Trends Biochem. Sci., 14, 272, 10.1016/0968-0004(89)90062-5 Feizi, 1991, Carbohydrate differentiation antigens: probable ligands for cell adhesion molecules, Trends Biochem. Sci., 16, 84, 10.1016/0968-0004(91)90038-W Varki, 1994, Selectin ligands, 91, 7390 Takayama, 1997, Chemoenzymatic preparation of novel cyclic imine sugars and rapid biological activity evaluation using electrospray mass spectrometry and kinetic analysis, J. Am. Chem. Soc., 10.1021/ja971695f Murray, 1996, Mechanism and specificity of human α-1,3-fucosyltransferase V, Biochemistry, 35, 11183, 10.1021/bi961065a Takayama, 1996, Synthesis of lactosamine derivatives using β-D-galactosidase from bacillus circulans, Bioorg. Med. Chem. Lett., 6, 1123, 10.1016/0960-894X(96)00184-9