Donald E. Kiely

Donald E. Kiely
Professor and Director of the
Shafizadeh Rocky Mountain Center for Wood
and Carbohydrate Chemistry

Email: donald.kiely@umontana.edu

Phone: (406) 243-4435

Lab: (406) 243-6160

Don Kiely joined The University of Montana Chemistry Department in 1997 as Professor of Chemistry and Director of the Shafizadeh Rocky Mountain Center for Wood and Carbohydrate Chemistry. He was previously Professor of Chemistry at the University of Alabama at Birmingham where he ran an active research program in the area of synthetic carbohydrate chemistry for many years. Don earned his Ph.D. from the University of Connecticut in natural products chemistry under the direction of Dr. James Bobbitt, and then spent two years as an NIH Staff Fellow working with the late Hewitt G. Fletcher, Jr. Through the years he has carried out research in both academic and industrial settings while on sabbatical leaves. His current research interests in carbohydrate chemistry are focused on industrial development of carbohydrates. He is the founding and current editor of the Journal of Carbohydrate Chemistry. He teaches undergraduate and graduate level courses in organic chemistry at the U of M.

 

Research Interests

In this laboratory, carbohydrates are considered as inexpensive “renewable chemical feedstocks”, i.e., products from “agricultural oil wells”. We use these carbohydrate molecules as building blocks to synthesize an array of new “environmentally friendly” polymeric products. Taking that view means that one must address a reality about carbohydrate molecules - they are multifunctional molecules, yet require selective functional group transformations to convert them to other materials. Our challenge is in developing economic, regiospecific reactions on these mulifunctional compounds that are appropriate for industrial scale production of the target polymers.

“Polyhydroxypolyamides&rdqup; - In keeping with the above challenge we are conducting fundamental materials research directed to the development of new synthetic, biodegradable carbohydrate derived polyamides. These polymers, labeled Polyhydroxypolyamides (PHPAs), (or “Hydroxylated Nylons”), are novel copolyamides (I) composed of a carbohydrate diacid (aldaric acid, e.g. D-glucaric acid, meso-xylaric acid, D-galactaric acid, etc.) and a noncarbohydrate diamine repeating unit. A variety of structurally diverse diamines can be employed as diamine monomers. As an example, a generic poly(D-glucaramide) is shown below.

structure of phpas

Application of our technology has generated a wide range of polyamides of this type. The synthetic methods are efficient, versatile and require no protection/deprotection steps. This has allowed us to make families of polymers whose properties are influenced in a reasonably predictable way by their component carbohydrate diacid and diamine monomer units. Polymers are characterized using standard methods that include elemental analysis, NMR, GPC with online molecular weight determinations, DSC and TGA analyses. Molecular modeling is a vital component of this research.

Chemistry of unprotected carbohydrates - syntheses and solution studies using high field NMR. There has been a long-term effort in our laboratory directed toward devising simple and efficient synthetic routes to particular cyclitols and novel dicarbonyl sugars, small molecules of biological interest. Use of high field NMR is essential in analysis of complex anomeric (isomeric) equilibrium mixtures of the latter sugars, key precursors of the target cyclitols.

The research labs of the Shafizadeh Center are located on the fourth floor of the University of Montana Science Complex, right next to the Chemistry Department building. The laboratory is equipped with HPLC and GC/MS equipment, plus a large computer controlled reactor for reaction development and control. Lots of windows in the labs provide wonderful views of the mountains that surround the Missoula valley.

Representative Publications

J. Zhang, D.E. Kiely and K. I. Hardcastle,”MM3 Conformational Analysis and X-Ray Crystal Structure of 2,3,4,5-tetra-O-acetyl-N,N’-dimethyl-D-glucaramide as a Conformational Model for the D-Glucaryl unit of Poly(alkylene-2,3,4,5-O-acetyl-D-glucaramides”, J. Carbohydr. Chem., 25, 633-659, 2006.

J. Zhang and D. E. Kiely, “Application of a Model Building Approach to Molecular Mechanics (MM3) for Calculating Low Energy Conformations of Tetra-O-N,N’-dialkyl-D-glucaramides to Predict Corresponding Polyamide Secondary Structure”, J. Carbohydr. Chem., 25, 697-711, 2006.

Lee-Davey, C., Manley-Harris, M. and Kiely, D.E., “Esterification of select polyols with D-glucaric acid as model reactions for esterification of starch”, Carbohydr. Res., 341, 2688-2693, 2006.

Thomas Jahns and Donald E. Kiely, “Abiotic Hydrolysis of Some Poly-D-Glucaramides and Subsequent Microbial Utilization / Degradation”, Journal of Polymers and the Environment, 14, 165-169 (2006).

Donald E. Kiely, “Carbohydrate Diacids: Potential as Commercial Chemicals and Hydrophobic Polyamide Precursors”, ACS Symposium Series 784, Chemicals and Materials from Renewable Resources, Ed. J. J. Bozell, pp 64 -81,2001.

Donald E. Kiely, Liang Chen, and Tsu-Hsing Lin,, “Synthetic Polydroxypolyamides from Galactaric, Xylaric, D-Glucaric and D-Mannaric Acid and Alkylenediamine Monomers - Some Comparisons”, J. Polym. Sci.; Polym Chem. Ed, 38, 598 (2000)

David W. Morton and Donald E. Kiely, “Synthesis of Poly(azaalkylene aldaramides) and Poly(oxaalkylenealdaramides) Derived from D-Glucaric and D-Galactaric Acids”, J. Polym. Sci.; Polym. Chem. Ed., 38, 404 (2000).

David W. Morton and Donald E. Kiely, “Evaluation of the Film and Adhesive Properties of Some Block Copolymer Polyhydroxypolyamides from Esterified Aldaric Acids and Diamines”, J. Applied Polym. Sci., 77, 3085 (2000).

A. Carter, D. W. Morton and D. E. Kiely, “Synthesis of Some Poly(4-alkyl-4-azaheptamethylene- D-glucaramides)”, , J. Polym. Sci.; Polym. Chem. Ed., J. Polym. Sci.; Polym. Chem. Ed., 38, 3892 (2000).

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