Solid phase synthesis - designer linkers for combinatorial chemistry: a review
Kirsteen Gordon and Shankar Balasubramanian
Journal of Chemical Technology and Biotechnology, 74, 835-851 (1999) Abstract
Solid phase organic synthesis is a rapidly expanding area of synthetic chemistry which is being widely exploited in the search for new biologically active compounds by combinatorial techniques. This review introduces the key concepts of solid phase methodology and combinatorial synthesis with particular focus on the issues that concern the development of linkers which are used to attach the substrate to the solid support. Full Text (PDF)
Combinatorial Carbohydrate Synthesis
S. Nacak Baytas and R.J. Linhardt
Mini-Reviews in Organic Chemistry, 2004, 1, 27-39 Abstract
Combinatorial chemistry has contributed to the preparation of biologically important oligosaccharide and glycoconjugate libraries, with a view of improving our understanding of the complex interaction between the carbohydrates and their protein-based receptors. The combinatorial carbohydrate synthesis strategies, developed in the past decade, provide access to small and medium size libraries. This mini review critically examines both the solution phase and solid phase strategies that have been reported to date. Full Text (PDF)
Solid-Phase Synthesis: a Paradigm Shift
Garland R. Marshall
Department of Biochemistry and Molecular Biophysics
Washington University Medical School, 700 S. Euclid Avenue, St. Louis, MO 63110, USA Abstract
A personal review by the first graduate student of Prof. R. Bruce Merrifield of the evolution of solid-phase synthesis and its acceptance by various subsets of the chemistry community. Solid-phase synthesis, as currently practiced in the synthesis of biopolymers, combinatorial solid-phase organic chemistry, synthesis of natural products, catalyst selection, chemical ligation, and materials development, has proven a paradigm shift for the chemistry community. Full Text (PDF)
Solid Phase Synthesis of Polyamides Containing Imidazole and Pyrrole Amino Acids
Eldon E. Baird and Peter B. Dervan
J. Am. Chem. Soc. 1996, 118, 6141-6146 Abstract
The solid phase synthesis of sequence specific DNA binding polyamides containing N-methylimidazole (Im) and N-methylpyrrole (Py) amino acids is described. Two monomer building blocks, Boc-Py-OBt ester and Boc-Im acid, are prepared on a 50 g scale without column chromatography. Using commercially available Boc-β-alanine-Pam resin, cycling protocols were optimized to afford high stepwise coupling yields (>99%). Deprotection by aminolysis affords up to 100 mg quantities of polyamide. Solid phase methodology increases both the number and complexity of minor groove binding polyamides which can be synthesized and analyzed with regard to DNA binding affinity and sequence specificity. The solid phase synthesis of a representative eight-residue polyamide is reported. Full Text (PDF)
