Troy Edward Wilson

The solid phase synthesis of N-alkylcarbamate oligomers

Abstract An efficient method for the solid phase synthesis of N -alkylcarbamate oligomers from alternating carboxylic acid and N α -Fmoc protected chiral p -nitrophenylcarbonate monomers has been developed. The general synthetic scheme involves four steps per coupling cycle: deprotection of the terminal amino group of the growing oligomer, acylation of the free amine with a carboxylic acid monomer, reduction of the resulting amide bond with borane and coupling of the secondary amine to a N α -Fmoc protected p -nitrophenyl carbonate monomer. This novel biopolymer which has two side chain residues per backbone carbamate linkage and no backbone hydrogen bond donors may provide new frameworks for drug design as well as folded domains with novel physical and biological properties.

SYNTHESIS OF A CYCLIC UREA AS A NONNATURAL BIOPOLYMER SCAFFOLD

A cyclic urea trimer was synthesized from readily available amino acid derivatives using a simple, iterative approach. A selective amide reduction using borane (BH3-THF) and a triphosgenemediated cyclization are the key features in a synthesis of the cyclic urea trimer 2.

Scanning Tunneling Microscopy at High Gap Resistances and on Chemically Modified Silicon Surfaces

Scanning tunneling microscopy (STM) studies of organic or biological molecules are difficult to reproduce because strong tip‐surface interactions can displace weakly bound material at the surface. We have studied conducting organic monolayers and nucleic acids with our STM instrument at high gap resistance values (100 GΩ to 1 TΩ). We have succeeded in imaging chemically modified silicon surfaces. It is our desire to use these chemically modified surfaces in conjunction with higher gap values in the future to reliably image DNA.