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To overcome this limitation, parallel detection methods, which have been implemented for a number of different analytical techniques for increasing throughput,29,30,31,32 are highly desirable for NMR detection. To date, several parallel NMR methods have been developed,33,34,35,36,37,38,39,40 including a new methodology called multiplex NMR37,38,39 developed in our laboratory. Recent developments in high-throughput NMR indicate that, with further development, parallel NMR techniques will play an important role in highthroughput chemical analysis and drug screening. 7.1.1. High-Throughput Analytical Techniques for Combinatorial Library Analysis
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The concept of combinatorial chemistry was rst introduced by Merri eld41 in 1986, and involved solid-phase synthesis methods to generate small mixtures of immobilized peptides. This idea was further developed in the early 1990s by Geysen, Dibo, Houghten, and their co-workers.42,43,44 Their technique represented a completely different synthesis method capable of generating vast number of compounds in a relatively short period of time compared to classical synthetic chemistry. Combinatorial chemistry was initially developed for solid-phase peptide and oligonucleotide synthesis, but because of the poor bioavailability of these biopolymers, the interests of synthesis have shifted to peptidomimetics (compounds that can mimic the critical features of the molecular recognition process of the parent peptide) and small organic molecules (MW < 700 Da).45 In its original implementation the split-couple-recombine (or split-and-mix) methodology was adopted to produce one to several mixtures or libraries of products through a randomization process.41 Although the split-and-mix synthesis technique is still used by many chemists, it has been largely replaced by automated parallel solid-phase and solution-phase synthesis, which are of high speed and spatially addressable.6,7,8 Compared to combinatorial chemistry, parallel synthesis approaches can produce large collections of individual compounds (as opposed to mixtures) in larger quantities that can be puri ed and more rigorously analyzed, which makes it easier to characterize, screen, and maintain the combinatorial libraries. However, unless speci cally stated otherwise, we will include both parallel and split-and-pool syntheses under the de nition of combinatorial chemistry in our discussions below. Combinatorial approaches make it relatively straightforward to generate chemical libraries with vast number of new compounds; thus synthesis is often no longer the rate-limiting step in drug discovery. Since almost all analytical characterization tools are serial techniques, the puri cation and analysis of the chemical libraries has instead become a new bottleneck. This, of course, imposes new analytical challenges in the elds associated with
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combinatorial chemical library analysis
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combinatorial chemistry, and more rapid and robust analytical approaches are in great need to keep pace with the new paradigm. Analytical techniques such as IR, NMR, uorescence spectroscopy, MS, GC, and HPLC have historically been used in drug discovery and other areas to characterize new compounds. These techniques are now being adapted for use in combinatorial chemistry and high-throughput screening applications to facilitate the analysis of new compounds and the identi cation of promising leads. However, each of the analytical techniques has its own limitations in the analysis of combinatorial libraries. For example, techniques such as GC and uorescence spectroscopy are not applicable to the identi cation of most new chemical entities, while IR and MS are not speci c enough to determine chemical structures unambiguously, and other techniques, such as HPLC and NMR spectroscopy, suffer from low throughput or sensitivity. Due to its high speed and high sensitivity, mass spectrometry is one of the most widely used techniques in combinatorial library analysis,46 and high-throughput MS methods have been developed to accommodate the needs of analyzing large numbers of compounds in combinatorial libraries. Chemiluminescence nitrogen detection (CLND),47 a method that provides linear response to the absolute amount of nitrogen from most nitrogen-containing analytes, can be used as a tool to determine the concentrations of pure compounds accurately and rapidly down to lowpicomole levels. CLND is easy to couple with other techniques, such as GC, LC, and recently has been utilized as a quantitative tool in combinatorial library analysis.48,49 Mass spectrometry provides the means to characterize new compounds based on their molecular weight and to a lesser extent structure. At the same time, MS methods are often high-throughput and can be coupled with chromatographic separation techniques. There are two widely adopted approaches for high-throughput mass spectrometric analyses of combinatorial libraries: ow injection analysis mass spectrometry (FIA-MS) and liquid chromatography mass spectrometry (LC-MS). Due to its simplicity in design and operation, FIA-MS has become the most widely utilized mass spectrometric method for characterizing combinatorial chemical libraries, and it is also the mass spectrometric based technique with the highest throughput.46 In addition to coupling an FIA-MS system with an autosampler, parallel sampling methodologies have been implemented into the FIA-MS system,50,51 and therefore the throughput of FIA-MS has been improved signi cantly. LC-MS is usually used for rapid purity assessment of the compound libraries. Because LC-MS has advantages over FIA-MS in its ability to analyze mixtures and to provide more complete characterization of compound libraries, it has replaced FIA-MS as the standard analysis tool in
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