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Louis A. Silks III

Pete Silks

Capabilities

  • Biosciences
  • Algal biofuels
  • Natural products
  • Cellulose breakdown
  • Chemical Science
  • Biological chemistry
  • Organic chemistry
  • Lipid conversion
  • Algal biofuels
  • National Stable Isotope Resource
  • Chemical synthesis
  • Lignin and cellulose breakdown

Expertise

Establishment of a new research program in Bioenergy — this activity uses a carbon chain extension of carbohydrates aldol reaction followed by reduction/deoxygenation to give rise to transportation fuels. 

Develop programs to leverage external  funding (DOE, DTRA, NIH, NCI, and industry).  

Responsible for conceiving and developing a stable isotope program for the syntheses of 2H, 13C, 15N, 17,18O, 77Se, labeled nucleic acids, amino acids, carbohydrates and investigations into new synthetic methods using chiral biomedically important compounds.

 

Education

Ph.D., Organic Chemistry, Boston University, Department of Chemistry, 1985
Thesis Title:  Investigations of the Addition of Organocuprates to a-Oxoketene Dithioacetals.

B.S., Biology, Biochemistry, cum laude, Suffolk University (in Boston), 9/1978

 

LANL Positions

Scientist 4, Bioenergy Group, B11, 10/2012 - present 

Staff Member:  Bioscience Division, Los Alamos National Laboratory, 1990 - present
Responsible for conceiving and developing a stable isotope program for the syntheses of 2H, 13C, 15N, 17,18O, 77Se, labeled nucleic acids, amino acids, carbohydrates and investigations into new synthetic methods using chiral biomedically important compounds.

 Acting Deputy Group Leader, Group B8, 4/2012 - 10/2012

Team Leader for Bioscience Division, Group B8, 6/2007 - 10/2012
Activities involve establishment of a new research program in Bioenergy. This activity uses a carbon chain extension of carbohydrates aldol reaction followed by reduction/deoxygenation to give rise to transportation fuels. Also, develop programs to leverage external funding (DOE, DTRA, NIH, NCI, and industry). I have a Q level security clearance and previously held a SCI clearance.

Group Leader, Biotechnology, Spectroscopy, and Isotope Chemistry (Group B3), Bioscience Division, Los Alamos National Laboratory, 2003 - 6/2007
Group B3 was composed of 40-50 people who were housed in 4 different facilities that are widely dispersed across the LANL site. The group was supported by an $8 M/y budget.  There were 12 PIs (faculty equivalent), 13 technicians, ~20 students (graduate and postdoctoral), and one contract person (retired Professor). The capabilities within the group ranged from synthesis, biotechnology, spectroscopy and isotope chemistry. Performed salary management and performance summaries for all B3 UC and LANS employees. Provided high-level management of the group and leadership direction for Bioscience Division.    

Also, contributed to B-Division Business development activities by promoting Stable Isotopes, CDC contracts, DTRA/DHA national security work, and Metabolomics as growth areas. Wrote business plan to reflect this. Nurtured a broad technical base and promoted applications to the Intel community.  Obtained a SCI clearance (for CIA discussions) to foster activities in this area. Increased the Division’s intellectual property portfolio. All deliverables provided on time and on budget.

 

 

Professional Societies

American Association for the Advancement of Science

American Chemical Society

 

Awards

LANL NNSA P2 and Sustainability Award, for innovative technologies for cost effective production of algal biomass and lipids, cash award, 2011    

Distinguished LANL Performance Award for a Large Team, “LANL Algal Biofuels Consortium Development Team,” 2010   

Outstanding Innovation award for Patent Recognition-piperazine technologies for medicalapplications, license revenue $4000, 2009

Los Alamos Awards Program, $750 for exceptional contributions and noteworthly achievements serving on the LANL WSST, 2008

Outstanding Innovation award for Patent Recognition - piperazine technologies for medical applications license revenue $3500, 2008

Outstanding Innovation award for Patent Recognition - Stable Isotope Labeling technologies $250, 2007 

Honorarium for Executive Editorship of Current Organic Chemistry $400, 2006

Outstanding Innovation award for Patent Recognition - Stable Isotope Labeling technologies $1.9K,  2006

Directors Award for Participation in the LANL Stand Down Management Self Assessment $900, 2005

Outstanding Innovation award for Patent Recognition - Influenza Sensor $300, 2004

Bioscience Division award for outstanding achievement $300 for programmatic development-CDC project, 2003

Bioscience Division award for outstanding achievement $300 for programmatic development-resuscitation of the NIH Stable Isotope Resource, 2001

Los Alamos National Laboratory Achievement Award for the successful programmatic relocation of the SIR organic synthesis capability, 1997

DOT (Division Office Technical) appointment from CST Division of LANL for 1995, half time appointment ($130 K) to commercialize new stable isotope labeling strategies, 1994

Article published in Chemical and Engineering News 1994, March 28, page 42, this was written by Dr. Stephen Stinson and it detailed our development of a high yield synthesis of 13C labeled glycerol, 1994

R & D-100 Award, this was awarded to Los Alamos National Laboratory in a annual national competition by R & D magazinehere are 100 awarded per annum, 1993 

Article published in Chemical and Engineering News 1990, 68, 25, this was written by Dr. Stephen Stinson and it detailed our development of a selenium-based reagent for the determination of chiral purity, 1990

American Cancer Society Grant, awarded to initiate startup of a synthetic approach toward the anticancer drug Taxol, 1988 

Biomedical Research Seed Grant, awarded to initiate startup of investigations into the use of tellurium-labeled oligonucleotides for use as probes in their interaction with DNA, 1988

Full Scholarship, Boston University, 1978 - 1984

Citation for Excellence in Teaching, Organic Chemistry, 1982

Polaroid Corporation Grant, received for continuing research during summer term, this was a highly competitive award and only one is given out per annum, cash award $1,200, 1982 

Citation for Excellence in Teaching, Freshman Chemistry, Boston Univerisity, 1979

Graduated CUM LAUDE, Suffolk University, 1978

Dean's Lis, Suffolk University, 1976-1978

Sigma Chi Fraternity Scholarship, University of Kansas, 1974  

 

Patents

Chalcogen-Based Chiral Reagents For The Nuclear Magnetic Resonance Detection Of Stereochemical Assignments And Enantiomeric Ratios. Submitted to the University of South Carolina Patent and Copyright Committee on July 20, 989.  Filed in the United States patent office 10/6/1989. Awarded 6/16/1992.  Patent No. 5,122,472

Chalcogen-Based Chiral Reagents For The Nuclear Magnetic Resonance Detection Of Stereochemical Assignments And Enantiomeric Ratios.  Filed in the Unitied States patent office March 5, 1993. U.S. Patent Appln. S.N. 08/027,552. U.S. Patent No 5,344,936

Aldol Chemistries Of Chiral N-Acyl Selones. LAD-99-028.  U.S. Patent Application Serial No. 09/439,481. U.S. Patent 6,448,409

Influenza Sensor. LAD-99-034.  Patent Issued. US 2003, 6,627,396

Generic Membrane Anchoring System For The Detection Of Receptor Binding. Submitted 11/2000. LAD-2000-128  

Synthesis of [2H, 13C], [2H2, 13C] and [2H3,13C]Methyl Aryl Sulfones And Sulfoxides. Issued Patent 6,764,673

Synthesis of Labeled Metabolites. Issued Patent 6,709,645

Synthesis of 2H- and 13C-Substituted Compounds.  Issued Patent 6,730,805

Synthesis Of [2H, 13C], [2H2, 13C] And [2H3,13C]Methyl Aryl Sulfides. Issued Patent 6,713,044

Third Generation Of Oligonucleic Acids Analogs; Potential Application Of New Piperazine Based Nucleic Acids. LAD-2000-105. DOE no. S-94,759. Issued Patent 6,841,675

Patent Application Title: “Mining of Stable Isotope Metabolomic Pathyways for Microbial Diagnostics.” S# 10-29. Joint with the University of New Mexico 

Patent Title: “Selective catalytic method for the oxidation of industrially useful alcohols to aldehydes.” S#10-230. U.S. Patent Application No. 13/414,975 Filed 03/08/2012

“Method of Carbon Chain Extension using Novel Aldol Reaction”, US application 20110040110, filed 8/17/2009.

“Method of Carbon Chain Extension using Novel Aldol Reaction”, US  application 20110040109, filed 8/17/2009.

“Compounds and Methods For the Production of Long Chain Hydrocarbons From Biological Sources”, 1st US Provisional Patent Application No. 61/534,496, filed September 14th, 2011; 2nd US Provisional Patent No. 61/669,775, filed 7/10/2012

“One Step Conversion of Oligomeric Starch or Cellulose to Single C10 or C11 Carbon Chains Furans and their Conversion to Fuel Hydrocarbons”, US Provisional Patent Application No. 61/669,980, filed 7/10/2012

“Compounds and Methods for the Production of Long Chain Hydrocarbons From Biological Sources”, International Patent Application No. PCT/US2012/055340 filed Sept. 14, 2012 (claiming priority of US provisional Application nos. 61/534,496, filed Sept. 14, 2011 & 61/669,775, filed 7/10/2012

“Conversion of Oligomeric Starch, Cellulose or Sugars to Hydrocarbons”, International Patent Application No. PCT/US2012/055337 filed Sept. 14, 2012 (claiming priority of US provisional application  no. 61/669,980,  filed 7/10/2012

 

Publications

Li, Z., Wu, R., Michalczyk, Dunlap, R. B., Odom, J. D., Silks, L. A., "Stereoselectivity in Aldol Reactions of Chiral N-acyl Selones," J. Am. Chem. Soc. 2000, 122(2), 386, as a communication

Michalczyk, R., Schmidt, J., Moody, E., Zizhong, L., Wu, R., Dunlap, R. B., Odom, J. D., Silks, L.A., "Unusual C-H•••Se=C Interactions in Aldols of Chiral N-Acyl Selones Detected by Gradient Selected 1H-77Se HMQC NMR Spectroscopy and X-Ray Crystallography," Angewandte Chemie 2000, 39 (17), 3067.

Yang, J., Silks, L. A., Wu, R., Isern, N. G., Unkefer, C. J., Kennedy, M. A. “A Comprehensive Approach for Accurate Measurement of Proton-Proton Coupling Constants in the Sugar Ring of DNA” J. Mag. Res., 2000, 146 (2), 260.

 Stocking, E. M., Martinez, R. A., Silks, L. A., Sanz-Cervera, J. F., Williams, R. M "Studies on the Biosynthesis of Paraherquamide: Concerning the Mechanism of the Oxidative Cyclization of L-Isoleucine to b-Methylproline” J. Am Chem. Soc. 2001, 122, 1675.

Tomson, F., Bailey, J. A.,  Gennis, R. B., Unkefer, C. J., Li, Z., Silks, L. A., Martinez, R. A., Donohoe, R. J., Dyer, R. B., Woodruff, W., “Direct Infrared Detection of the Covalently Ring-Linked His-Tyr Structure in the Active Site of the Heme-Copper Oxidases,” Biochemistry, 2002, 41(48), 14383-14390.

Kimball, D. B., Michalczyk, R., Moody, E., Ollivault-Shiflett, M., DeJesus, K., Silks, L. A. P. “Determing the Solution State Orientation of a Ti Enolate via Stable Isotope Labeling, NMR Spectroscopy, and Modeling Studies,” J. Am. Chem. Soc. 2003, 125 (48), 14666.

Kim, S. H., Aznar, C., Brynda, M., Silks, L. A., Michalczyk, R., Unkefer, C. J., Woodruff, W. H., Britt, D. R. “An EPR, ESEEM, Structural NMR, and DFT Study of a Synthetic Model for the Covalently Ring-linked Tyrosine-histidine Structure in the Heme-copper Oxidases” J. Am. Chem. Soc. 2004, 126, 2328.  

Gray, C. R., Sanz-Cervera, J. F., Silks, L. A., Williams, R. M. “Studies on the Biosynthesis of Asperparaline A:  Origin of the Spirosuccinimide Ring System,” J. Am. Chem. Soc. 2003, 125 (48), 14692.

Kim, S. H., Aznar, C., Brynda, M., Silks, L. A., Michalczyk, R., Unkefer, C. J., Woodruff, W. H., Britt, D. R. “An EPR, ESEEM, Structural NMR, and DFT Study of a Synthetic Model for the Covalently Ring-linked Tyrosine-histidine Structure in the Heme-copper Oxidases” J. Am. Chem. Soc. 2004, 126, 2328.

Hatch, D., Boles, J. O., Li, Z., Silks, L. A. “Synthesis and Applications of Selenium and Tellurium Containing Amino Acids,” Curr. Org. Chem.  2004, 8 (14), 47. 

Mariappan, S. V. S., Cheng, X., van Breemen, R., Gupta, G, Silks, L. A. “Destabilization of GAA/TTC DNA Triplexes: Nuclear Magnetic Resonance and Mass Spectrometric Assays,” Anal. Chem. 2004, 334 (2), 216.

Ollivault, M.; Kimball, D. B.; Silks, L. A. “Synthesis of Chiral 13C,77Se-Labeled Selones,” J. Org. Chem. 2004, 69(15), 5150.

Boyer, A. E., Ash, D., Barr, D. B., Young, C. L., Driskell, W. J., Whitehead, R. D., Jr., Ospina, M., Preston, K. E., Woolfitt, A. R., Martinez, R. A., Silks, L. A. P., Barr, J. R.  “Quantitation of the Sulfur Mustard Metabolites 1,1'-Sulfonylbis[2-(methylthio)ethane] and Thiodiglycol in Urine Using Isotope-Dilution Gas Chromatography Tandem Mass Spectrometry,” Journal of Analytical Toxicology  2004,  28(5), 327.

Young, C. L., Ash, D., Driskell, W. J., Boyer, A. E., Martinez, R. A., Silks, L. A., Barr, J. R.  “A Rapid, Sensitive Method for the Quantitation of Specific Metabolites of Sulfur Mustard in Human Urine Using Isotope-Dilution Gas ChromatographyETHTandem Mass Spectrometry,” Journal of Analytical Toxicology  2004, 28(5),  339.

McAteer, K., Aceves-Gaona, A., Michalczyk, R., Buchko, G. W., Isern, N. G., Silks, L. A., Miller, J. H.,  “Compensating Bends in a 16-base-DNA Oligomer Containing a T3A3 Segement: A NMR Study of Global DNA Curvature,” Biopolymers 2004, 75 (6), 497.

Kimball, D. B, Shiflett, S., Silks, L. A. P. “Current Progress in the Acetate/Methyl Ketone Aldol Reaction,” Curr. Org. Chem. 2006, 10 (15), 1975.  This was an invited review article.

Silks, L. A. P., Kimball, D. B., Hatch, D., Olivault-Shiflett, M., Michalczyk, R., Moody, E. “Chrial N-Acetyl Selone-Promoted Aldol Reactions,” Syn. Comm.  2009, 39, 641.

Liu, X., Silks, L. A., Ollivault-Shiflett, M., Li, J., Wang, Y., Yu, H., Liu, J., Shen, J. “Bioincorporation of Tellurocysteine into Glutathione Transferase Installs High Glutathione Peroxidase Efficiency,” Angew. Chem. 2009, 48, 2020. 

Kumkum, G., Wu, R., Ollivault-Shiflett, M., Goodwin, P. M., Silks, L. A. “Design, synthesis and a novel application of quorum sensing agonists as potential drug-delivery vehicles,” Journal of Drug Targeting 2010, 19(7), 528-539.

Hanson, S. K., Baker, T. R., Gordon, J. C., Scott, B. L., Silks, L. A., Thorn, D. L. “Mechanism of Alcohol Oxidation by Dipicolinate Vanadium (V): Unexpected Role of Pyridine” J. Am. Chem. Soc. 2010, 132, 17804.

Hanson, S. K., Wu, R., Silks, L. A. “Mild and Selective Vanadium-Catalyzed Oxidation of Benzylic, Allylic, and Propargylic Alcohols Using Air” Org. Lett. 2011, 13(8), 1908.

Sedai, B., Diaz-Urrutia, C, Baker, R. T., Wu, R., Silks, L. A. P., Hanson, S. K. “Comparision of Copper and Vanadium Homogeneous Catalysts for Aerobic Oxidation of Lignin Models” Catalysis, 2011, 1, 794.  

Hanson, S. K., Wu, R., Silks, L. A. “C-C or C-O Bond Cleavage in a Phenolic Lignin Model Compound: Selectivity Depends on Vanadium Catalyst” Angew. Chem. 2012, 51, 3410.  Also, was illustrated on the inside cover. 

Waidmann, C. R., Pierpont, A. W., West, R., Batista, E. R., Gordon, J, C., Martin, R. L., Silks, L. A. P., Wu, R., “Catalytic Ring Opening of Furan Rings Within Biomass Derived Substrates: An Experimental and Theoretical Study” Catalysis Science and Technology 2013, 3, 106, and is illustrated on the front cover. 

Keith, J. M., Kim, J. K., Alexander, L., Wu, R., Martin, R. L., Batista, E. R., Michalczyk, R., Scott, B., Hanson, S. K., Sutton, A. D., Gordon, J, C., Silks, L. A. P., “Aqueous Organocatalysis Applicable to the Carbon Chain Extension of Carbohydrate Derivatives: Application to the Production of Transportation Fuels” Current Organic Chemistry 2013, accepted.

Alexander, L., Hoyt, C., Michalczyk, R., Thorn, D., Wu, R., Silks, L. A. P.* One Step Synthesis of [1,6- and U-13C]Levuglucosan From Labeled Glucose” Journal of Labelled Compounds and Radiopharmaceuticals 2012, 56, 27. 

Schmidt, J., Lodwig, S., Silks, L. A. P.*, Wu, R.* “Synthesis of 13C Labeled  Sulfur and Nitrogen Mustard Metabolites as Mass Spectrometry Standards for Monitoring Chemical Warfare Agent Exposure,” Journal of Labelled Compounds and Radiopharmaceuticals 2012, 55, 211.

Zhang, G., Scott, B. L., Wu, R., Silks, L. A. P., Hanson, S. K. “Aerobic Oxidation Reactions Catalyzed by Vanadium Complexes of Bis(Phenolate) Ligands,” Inorganic Chemistry 2012, 51, 7354. 

Sutton, A. D., Waldie, F., Wu, R., Schlaf, M, Silks, L. A. P. Silks, Gordon, J. C. “The Hydrodeoxygenation of Bioderived Polyols into Alkanes,” Nature Chemistry 2013, accepted.  

Sutton, A. D., Kim, J. K., Hoyt, C. B., Wu, R., Kimball, D. K., Silks, L. A. P., Gordon, J. C. “Conversion of Oligosaccharides into Branched Alkanes,” Science 2012, to be submitted. 

Wu, R., Silks, L. A., Olivault-Shiflett, M., Williams, R. F., Ortiz, E. G., Stotter, P., Martinez, R. A., “A General Route for 13C Labeled Fluorenols and Phenanthrenols via Palladium Catalyzed Cross Coupling and One-Carbon Homologation,” Journal of Labelled Compounds and Radiopharmaceuticals 2013, accepted.

C. R. Waidmann, L. A. “Pete” Silks, R. Wu, J. C. Gordon: “Rapid, Simultaneous Reduction of Olefins and Ketones in a Non-food Biomass Derived Substrate Using Simple Copper Catalysts”, Catalysis Science and Technology, published online 7th Feb 2013 (http://pubs.rsc.org/en/content/articlepdf/2013/cy/c3cy20762e).