This thesis is divided into two subjects: (1) molecular (chemical) evolution using intramolecular acyl migration on carbohydrate model, and (2) fluorescent rosamine library synthesis and its application to sensor development. In chapter 1, an intramolecular acyl migration was investigated as a potential strategy for constructing a carbohydrate dynamic combinatorial library (DCL). In a simple model such as inositol di/tri-benzoates, an intramolecular benzoyl migration on inositol was utilized to generate a DCL comprising various regioisomers under basic conditions. Selection events by phenylboronic acid/boric acids led to the amplification of the best binders with decrease of others, demonstrating the feasibility of intramolecular acyl migration for effective DCL generation and amplification.

Chapter 2 describes a diversity-oriented approach for the development of specific bioanalyte sensors. A combinatorial library of fluorescent rosamine dyes was synthesized by a novel solid-phase route, generating 240 highly pure distinct compounds. The fluorescence-based high-throughput screening toward 47 diverse bioanalytes identified two potential sensor/probes. First, one library member (G13) was found to exhibit a high selectivity and sensitivity to human serum albumin (HSA) over other bioanalytes that include highly structurally similar bovine serum albumin (BSA), and the potential of G13 for sensing HSA was described. Second, a potential fluorescent probe (H22) for a reduced glutathione (GSH) was discovered and evaluated for its capability of detecting the intracellular GSH levels in live cells. The elevated levels of GSH were monitored by fluorescence changes of H22 in microscopic imaging. Moreover, it was evaluated for monitoring the intracellular GSH depletion upon treatment of exogenous drug or drug-like molecules.