Biomimetic Chemistry in Water Solution

EPA Grant Number: R826653
Title: Biomimetic Chemistry in Water Solution
Investigators: Breslow, Ronald
Institution: Columbia University in the City of New York
EPA Project Officer: Lasat, Mitch
Project Period: August 3, 1998 through August 2, 2001
Project Amount: $376,747
RFA: Exploratory Research - Environmental Chemistry (1998) RFA Text |  Recipients Lists
Research Category: Sustainability , Land and Waste Management , Air , Engineering and Environmental Chemistry

Description:

The environmentally benign organic synthesis of substances such as pharmaceuticals, an important aspect of Green Chemistry, can be greatly aided by catalysts that operate in water, a benign solvent. Particularly appealing are biomimetic catalysts that imitate the ability of natural enzymes to perform selective reactions with good turnover and rate. If such catalysts are more rugged than proteins, and simpler, they would be preferable to natural enzymes, and could have different selectivities.

Approach:

We will build on recent advances in these laboratories by which novel catalysts have been synthesized using two or four cyclodextrin units to bind a substrate onto a metal catalytic unit in water solution. They promote selective fast reactions whose course is governed by the geometry of the complexes. We will examine the epoxidation or hydroxylation of other important substrates by our existing catalysts, including those that can lead to useful medicinal compounds that are currently prepared by less environmentally benign methods.

We will also change the catalyst. In one approach we will make it more stable, to increase the number of catalytic turnovers it performs before it is oxidatively destroyed. In another approach, we will change the mode of attachment of the binding groups to the porphyrin linker, so as to change the geometric selectivity of our systems. In yet another approach, we will change the nature of the binding group, exploring cyclodextrins other than the beta-cyclodextrin used so far, and other ways to attach the cyclodextrins. We will also examine synthetic binding groups that are not cyclodextrins, and the action of these catalysts on different substrates.

Expected Results:

We expect that our work will expand the range of chemistry that can be performed by imposing geometric catalytic selectivity in water solution. This can lead to general interest in such methods. Processes that are currently carried out using fermentation methods, or complex synthetic sequences, could be performed using biomimetic methods in a benign solvent, with an environmental advantage.

Publications and Presentations:

Publications have been submitted on this project: View all 26 publications for this project

Journal Articles:

Journal Articles have been submitted on this project: View all 18 journal articles for this project

Supplemental Keywords:

media, chemicals, chemical industry, pharmaceutical industry., Scientific Discipline, Air, Sustainable Industry/Business, Chemical Engineering, cleaner production/pollution prevention, Environmental Chemistry, Engineering, Chemistry, & Physics, geometric catalytic selectivity, water solution, cleaner production, medicinal compounds, pharmaceuticals, enzymes, catalysts, biomimetic synthesis, biometric chemistry, pollution prevention, biomimetic chemistry, green chemistry, pharmaceutical industry

Relevant Websites:

http://www.columbia.edu/cu/chemistry/breslow/boss.html Exit

Progress and Final Reports:

  • 1999
  • 2000 Progress Report
  • Final Report