A diversity oriented synthesis of natural product inspired molecular libraries

Diversity oriented synthesis of natural product inspired compounds from S-tryptophan methyl ester.

MethylN-(3-cyanopicolinoyl)-L-tryptophanate

In the title compound, C19H16N4O3, the stereocenter has an L configuration; L-tryptophan methyl ester hydrochloride being used as a starting material. The indole ring system and the pyridine ring are inclined to one another by 13.55 (14)°. In the crystal, adjacent molecules are linkedviaN—H...O hydrogen bonds, forming chains propagating along thec-axis direction.

Recognizing Amino Acid Chirality with Surface-Imprinted Polymers Prepared in W/O Emulsions

A molecularly imprinted polymer was prepared by a surface molecular imprinting technique in water-in-oil (W/O) emulsion. In this technique, the solid polymer, which is molecularly imprinted at the internal cavity surface, is prepared by polymerizing W/O emulsions consisting of a water-soluble imprinted molecule, a functional host molecule, an emulsion stabilizer, and a crosslinking agent. Dioleoyl phosphate was used as an emulsion stabilizer, and this compound also acted as a monomer and a host functional group in the imprinted cavity. Divinylbenzene was used as a crosslinker. Tryptophan methyl ester and phenylalanine methyl ester were used as the target template materials. These imprinted polymers exhibited enantiomeric selectivity in absorption experiments, and the maximum separation factor was 1.58. The enantiomeric selectivity with tryptophan methyl ester was higher than that with phenylalanine methyl ester.