peptoids and other Biomimetic Molecules

peptoids

Our lab studies a biomimetic molecule called peptoids. These are N-substituted glycine oligomers; essentially, they modify a peptide by moving the side chain from the alpha-carbon to the nitrogen. Peptoids have been used in a wide variety of applications in drug discovery and materials science. Other advantages of peptoids include:

Robust, flexible synthetic preparation
Favorable stability in biological systems

1. Peptoid Structure

We are interested in understanding peptoids' three-dimensional structures, particularly for water-soluble peptoids.

Sequence-structure relationships: what primary structure features contribute to peptoid three-dimensional structure? [more details here, or in this reference and this reference]
We develop new tools to study peptoid structure using spectroscopic techniques. [more details in this reference]

2. Peptoid Functions

We are evaluating the ability of peptoids prepared in our lab for:

pH sensing [more details in this reference]
molecular recognition and sensing small molecules [more details in this reference and this video]
interactions with silica surfaces and lipids (collaboration with Grace Stokes, Santa Clara University) [more details here, here, and here.]

Peptoid synthesis via the submonomer method:

Peptoid structure:

A 15-residue peptoid self-associates in water. We observe this using spectroscopy tools, including fluorescence (at right).

Peptoid function:

pH-Dependent conformational changes of a fluorescently labelled peptoid induce a 25-fold intensity change in the fluorescence emission.

At left, an amphiphilic peptoid helix self-assembles to make a supramolecular host for benzo[a]pyrene, a highly toxic molecule.

Other N-Substituted Oligoamides

We have also worked on preparing and studying other biomimetic molecules that are related to peptoids.

1. Azole peptoids and their cyclooligomers

We have prepared and studied azole peptoid oligomers, including efficient syntheses of their building blocks and cycloologomers and the interactions of linear azole peptoids with Zn2+ in water.

2. Arylopeptoids

Students enrolled in introductory organic laboratory courses have prepared combinatorial libraries of arylopeptoids.