A saccharide fluorescent receptor based on 1,1′-binaphthol was developed. The boronic acids groups are directly attached to the 3,3′-positions of BINOL which acted as probes to saccharides. The methyl protected receptor R1 showed better response to D-fructose compared to other saccharides in the fluorescence quenching experiment. To improve the selectivity of D-glucose, the triethylene glycol protected receptor R2 was developed. Receptor R2 has a better water-solubility than R1 that can be applied in completely aqueous environment. With receptor R2, D-glucose has a different response to other saccharides that can be useful for the distinction of D-glucose.

A 1,1′-bi-2-naphthol (BINOL)-based chiral aldehyde in combination with Zn^II shows a highly enantioselective fluorescent response toward functional chiral amines at λ>500 nm. However, the combination of salicylaldehyde and Zn^II gives the same fluorescent enhancement for both enantiomers of a functional chiral amine at λ=447 nm. By using the fluorescent responses of the combination of the BINOL-based chiral aldehyde, salicylaldehyde and Zn^II at the two emission wavelengths, both the concentration and enantiomeric composition of functional chiral amines such as amino alcohols, diamines, and amino acids can be simultaneously determined by a single fluorescent measurement. This work provides a simple and convenient method for chiral assay.

A practical transition-metal-free procedure for the synthesis of (E)-vinyl sulfones through the coupling of vinyl halides with sodium sulfinates in water is reported. The reaction is strongly influenced by the presence of acids, and the use of nBu₄NBr promotes its efficiency.

A series of 1, 4, 7, 10-tetraazacyclododecane (cyclen)-based cationic lipids, namely 5a–c bearing a biotin moiety and a variety of end groups (cholesterol, diosgenin, and α-tocopherol) via biodegradable carbamate bond linkage were prepared and applied as non-viral gene delivery vectors. The liposomes formed from 5 and dioleoylphosphatidylethanolamine could bind and condense plasmid DNA into nanoparticles with appropriate size and zeta potentials. All biotinylated cyclen cationic lipids showed higher cell viability than commercially available lipofectamine 2000 even at high N/P ratios, while their transfection efficiency was relatively lower. Further, results indicate that among the three lipids, α-tocopherol-containing compound 5c has higher DNA-binding ability, lower cytotoxicity, and higher transfection efficiency. Transfection in two different cell lines revealed that these lipoplexes have higher gene delivery efficiency toward tumor cells.

New imidazolium/benzimidazolium-containing receptors (R)-1–(R)-6 were developed as multifunctional receptors for both chromogenic and chiral anion recognition through multichannel. The ?uorescence spectra of (R)-1 showed a distinct and intense peak at 454, 474 nm with AcO⁻ and F⁻, respectively, indicating that (R)-1 can be applied to the detection of fluoride and acetate ions by naked eye. Receptor (R)-5, containing a lipophilic dodecyl appendage at imidazolium nitrogen, exhibited larger fluorescent responses than (R)-1. The ratio of fluorescence enhancement for (R)-5 with AcO⁻ (I₄₆₀/I₃₆₉=16) and F⁻ (I₄₈₅/I₃₆₉=11) was 32-fold and 18-fold over (R)-1 with AcO⁻ (I₄₅₄/I₃₆₉=0.5) and F⁻ (I₄₇₄/I₃₆₉=0.6), respectively. Less electron-deficient benzimidazolium receptor (R)-2 only gave fluorescence enhance at 555 nm for F⁻. Only chelation enhanced quenching (CHEQ) effect was obtained in the case of mono-imidazolium receptor (R)-4. Furthermore, (R)-1 and (R)-5 displayed a remarkable binding ability for the t-Boc alanine anion with interesting enantioselectivity [K_L/K_D=4.5 for (R)-1 and 4.1 for (R)-5)], whereas only negligible enantioselectivity ability (K_L/K_D=1.1) was obtained by using C₁ symmetric receptor (R)-4.

PPL, lipase from porcine pancreas, is first reported to catalyze direct asymmetric aldol reactions between aromatic aldehydes and cyclic ketones. More importantly, the catalytic activity of PPL was greatly promoted by a small quantity of water at 37 °C. A wide range of aromatic aldehydes reacted with cyclic ketones to provide the corresponding aldol products with high yields (up to 99 %) and moderate to good stereoselectivity (up to 90 % ee and 99:1 dr).

An efficient metal-free oxidative esterification of benzyl CH bonds was developed. Using tetrabutylammonium iodide as catalyst and tert-butyl hydroperoxide as co-oxidant, benzylic substrates could react smoothly with various carboxylic acids to give the esters with good to excellent yields. The method was also suitable for the O-protection of N-Boc amino acids. The reaction mechanism was primarily investigated and a radical process was proposed.

In this study, two novel cationic lipids containing protonated cyclen and quaternary ammonium moieties were designed and synthesized as non-viral gene delivery vectors. The structures of the two lipids differ in their hydrophobic region (cholesterol or diosgenin). Cationic liposomes were easily prepared from the lipids individually or from the mixtures of each cationic lipid and dioleoylphosphatidylethanolamine. Several studies including DLS, gel retardation assay, and ethidium bromide intercalation assay suggest that these amphiphilic molecules are able to bind and compact DNA into nanometer particles which can be used as non-viral gene delivery agents. Our results from in vitro transfection show that in association with dioleoylphosphatidylethanolamine, two cationic lipids can induce effective gene transfection in human embryonic kidney 293 cells, although the gene transfection efficiencies of two cationic lipids were found to be lower than that of lipofectamine 2000^TM. Besides, different cytotoxicity was found for two lipoplexes. This study demonstrates that the title cationic lipids have large potential to be efficient non-viral gene vectors.

Two novel cationic lipids based on protonated cyclen and steroid (cholesterol or diosgenin) moieties with carbamate linkage have been designed and synthesized for gene delivery. Cationic liposomes were easily prepared from each of these lipids individually or from the mixtures of each cationic lipid and dioleoylphosphatidyl ethanolamine (DOPE). Several studies including dynamic light scattering, gel retardation assay, ethidium bromide intercalation assay, and transmission electron microscopy (TEM) imaging demonstrate that these amphiphilic molecules are able to bind and compact DNA into nanoparticles which may act as nonviral gene delivery agents. Results from in vitro transfection show that in association with (DOPE), two cationic lipids can induce effective gene transfection in HEK 293, A549, and H460 cells. Especially, in tumor cells (A549 and H460), the gene transfection efficiency of two cationic lipids were found to be higher than that of commercially available Lipofectamine 2000. The lipoplexes formed from both cationic lipids were found to have low cytotoxicity in three cell lines even at high N/P ratios.