NMR Chemical Shift Calculations for Novel Bioactive Metabolites from an Acid Mine Waste Organism
EMSL Project ID
4394
Abstract
Metal contaminated mine-waste waters are a western regional problem in the US of major proportions. Remediation cost estimates range from $4-$50 billion dollars, and often remediation/recovery strategies must be tailored to specific sites due to the chemical differences in waste waters associated with ore bodies or waste rock dumps. The Berkeley Pit Lake in Butte, Montana is part of the largest EPA Superfund mine waste site in North America and sits at the headwaters of the Columbia River. Currently, the pit lake contains over 30 billion gallons of water that is highly acidic (pH=2.5), and contains vast concentrations of toxic metals such as aluminum, zinc, copper, and cadmium. Recent novel bioremediation strategies for the Berkeley Pit lake include isolation and study of the unique extremophiles recently discovered within the pit-lake system. To date over 40 fungi, bacteria, and algae have been isolated, cultured and are being investigated for biorediation and their adapted metabolic processes. The purpose of this study is to utilitze Hartree-Fock GIAO methods implemented in PNNL?s NWChem to investigate the unusually deshielded carbons in two novel polyketide-terpenoid metabolites isolated from a Penicillium species growing in the Berkeley pit-lake. Semi-emperical methods predict chemical shifts of d 69.7 and d 31.5, respectively for quaternary carbons C-11 and C-12, while NMR assignments are found to be d 71.2 and d 67.0, unusually deshielded for carbons not attached to an electronegative substituent. Ab initio, geometry optimized structures would also be compared with an X-ray crystal structure recently obtained for one of the metabolites.
Project Details
Project type
Exploratory Research
Start Date
2003-10-16
End Date
2005-12-16
Status
Closed
Released Data Link
Team
Principal Investigator
Related Publications
Zhang C, M Oostrom, JW Grate, TW Wietsma, and MG Warner. 2011. "Liquid CO2 Displacement of Water in a Dual-Permeability Pore Network Micromodel." Environmental Science & Technology 45(17):7581-7588. doi:10.1021/es201858r