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This chapter addresses both technical and strategic issues germane to the synthesis of chemical libraries that are targeted in nature. What makes a library targeted versus not targeted has not been clearly delineated in the literature (and is somewhat subjective), but here we define three ideological types (hit to lead, natural product inspired, and protein class targeted) and address topics relevant to their design and realization. Unbiased or prospecting libraries are dealt with in other chapters of the section and are not addressed here. Organizationally, an initial section on technical aspects of library construction is followed by sections dedicated to each ideological library type. For each section, a brief introduction is given on general considerations for the given library type, but a focus is placed on illustrative examples. This is not meant to be a comprehensive review, but care has been taken to identify specific examples that clearly illustrate both the intellectual and technical challenges of such an endeavor. An emphasis is placed on the initial discovery/hypothesis and how that is subsequently translated into the synthetic design and technical execution of the library.
A major demarcation between targeted and nontargeted libraries is commonly the size (how many discrete molecules synthesized) and the scale (the target mass of each final product). Targeted libraries are generally smaller in size but greater in scale; therefore, the experimental techniques used are not completely translatable from those used for libraries of large size. Consequently, the first section of this chapter addresses experimental techniques specifically geared toward libraries of smaller size but greater scale.
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