CURRICULUM VITAE

Dr. V. A. Soloshonok

FULL NAME:  SOLOSHONOK Vadim Anatol'evich   

NATIONALITY:  Ukrainian       

IMMIGRATION STATUS:  Permanent Residency in USA

ADDRESS:  Department of Chemistry and Biochemistry, University of Oklahoma, 620 Parrington Oval, Room 208,  Norman,  Oklahoma  73019-3051, USA

FAX: (405)-325-8279 (office); (405)-325-6111 (main departmental office)

Phone: (405)-325-8279 (office); (405)-325-4811 (main departmental office); (405)-360-1784 (home)

E-MAIL: vadim@ou.edu

Occupational Objectives

To serve on the faculty of a well-established chemistry department of a large university where my professional knowledge and research experience in organic chemistry, fluorine chemistry and asymmetric synthesis can be made available for the benefit of the students and the credit of the Institution.  To develop a superior quality research program in organic synthesis with emphasis on studies of novel reagents and reactions and their application in biologically/medicinally relevant fields. 

Research and Teaching Interests 

Exploratory, hard core synthetic organic chemistry: Reaction mechanisms; Development of novel chiral reagents and synthetic methodology for preparation of stereochemically defined organic compounds of biological and medicinal significance; Structure-activity relationship studies (medicinal chemistry); Asymmetric catalysis; General asymmetric synthesis; Asymmetric fluoro-organic chemistry (stereocontrolling effect of fluorine and fluorine-containing substituents); Biocatalysis; Biocatalytic resolutions of chiral compounds;  Computer aided chemistry (molecular modeling). 

Professional Research Experience

Department of Chemistry and Biochemistry, University of Oklahoma, Norman, OK, USA (08/01-present).

Associate Professor:  Currently: Building a superior quality organic chemistry laboratory and research program to attract highly motivated  graduate students and post-docs. 

Development of novel synthetic methodology for preparing virtually unknown bis-amino acids and related compounds.  Development of new type of peptide b-turn mimetics using the novel bis-amino acids as an element of C,C-cyclization. 

Further development of asymmetric [1,3]-Proton Shift Reaction for preparing amino-containing, polyfunctional biologically and synthetically important fluorine-containing compounds (drug candidates, catalysts for general asymmetric synthesis).

Development of novel methodology for general asymmetric synthesis of amino acids and relevant compounds. 

Development of practical and efficient methods for preparing sterically-constrained amino acids with presupposed conformational properties (chi-c-space) for rational design of peptides and peptide mimetics. 

 Studies of conformational and biological/physical properties/characteristics of fluorine-containing amino acids and peptides. 

Department of Chemistry, University of Arizona, Tucson, AZ, USA (08/98-08/01).

Visiting Scholar, from July 1^st, 2000 Research Scientist:  Development of practical, efficient approaches for stereocontrolled synthesis of highly constrained novel unnatural amino acids.  Design and synthesis of new peptidomimetics, peptide b-turns mimics and other scaffolds that can mimic peptides three-dimensional structures. 

•         Discovered an extraordinary efficient molecular recognition process between chiral non-racemic Ni-complexes of glycine or alanine and enantiomers of (1-bromoalkyl)benzenes.  The discovered phenomenon has been realized as a highly diastereoselective alkylation process for practical asymmetric synthesis of sterically constrained a,b-dialkyl substituted a-amino acids. 

•         Discovered highly diastereoselective Michael addition reactions between achiral Ni-complexes of glycine and chiral oxazolidin-2-one-derived a,b-unsaturated carboxylic acids, as an efficient and generalized methodology for preparing various poly-substituted glutamic acids and related compounds. 

•         Proposed, designed and realized new di-peptide isostere units and on this basis developed new generation of peptide b-turns mimics. 

National Industrial Research Institute of Nagoya, Aichi Pref., Nagoya, Japan (11/95-08/98).

Senior Scientist:  Development of highly enantioselective transfer of chirality from less to more configurationally unstable stereogenic centers, the stoichiometric asymmetric [1,3]-Proton Shift Reaction.  Development of practical strategies for stereoselective additions of stabilized C-nucleophiles to C,N double bond;  asymmetric syntheses of a,b-diamino carboxylic acids and amines. 

•         Discovered truly biomimetic one-stage biomimetic transamination process via reaction of fluoroalkyl carbonyl compounds with 4-picolylamine. 

•         Discovered highly enantioselective biomimetic transamination via azomethine-azomethine isomerization ([1,3]-Proton Shift Reaction) of the imines derived from perfluoroalkyl carbonyl compounds and (S)- or (R)-a-phenylethylamine, and applied it to the practical generalized asymmetric synthesis of enantiomerically pure fluorine-containing amino compounds (amines, amino acids) of biomedicinal importance. 

•         Discovered highly diastereoselective aza-aldol condensations between aldimines and a Ni(II) complex of Schiff base of glycine with (S)-o-[N-(N-benzylprolyl)amino]benzophenone. 

•         Discovered highly diastereoselective addition reactions of a-lithiated alkyl p-tolyl sulfoxides to fluoroalkyl N-PMP aldimines. 

The Academy of Science of Ukraine, Institute of Bioorganic Chemistry and Petrochemistry, Kiev, Ukraine 9/83-11/95).

Senior Research Associate: Leader of a research group consisting of eight persons (staff, undergraduate and Ph.D. students):  Design and development of practical strategies for preparing fluorine-containing amines, a-amino and a-hydroxy carboxylic acids.  Design and development of practical asymmetric methods for preparing enantiomerically pure organoelement analogs of amino acids.  Studies into biocatalytic resolutions of a- and b-amino acids by means of penicillin acylase. 

•         Discovered unusual reactivity of fluoroalkyl-containing azomethines and developed generalized reducing agent-free base-catalyzed biomimetic transamination method referred to as [1,3]-Proton Shift Reaction.  The reaction consists in the formation of Schiff base from fluoroalkyl carbonyl compounds and benzylamine, followed by its base-catalyzed isomerization to the corresponding N-benzylidene imine, which upon acidic hydrolysis gives rise to the targeted amino compound.  The reaction allows for large scale preparative transamination of fluoroaryl and fluoroalkyl aldehydes, ketones, a-, and b-keto carboxylic esters to fluoro-amines, a-, and b-amino acids of high biomedicinal importance.

•         Discovered and developed N-(alkoxycarbonyl/acyl)imines of trifluoropyruvic acid esters as versatile synthons for generalized synthesis of a-trifluoromethyl a-amino acids of biomedicinal importance.  Investigated reactivity and physical properties of the a-trifluoromethyl a-amino acids. 

•         Discovered and developed chemistry of trifluoropyruvic acid esters as a useful starting material for preparing various a-trifluoromethyl a-hydroxy acids via alkylation, cycloaddition and ene reactions. 

•         Discovered (R,S)-2-hydroxy-2-trifluoromethyl-trans-n-octadec-4-enoic acid as the first synthetic activator of 5-lipoxygenase. 

•         Developed chromatographic resolution of fluorine-containing a-, and b-amino acids, and amino acids possessing two chiral centers. 

•         Developed practical methods for preparing fluorine-containing derivatives of adamantane. 

•         Developed asymmetric methods for preparing enantiomerically pure fluoro- phosphorus- and sulfur-containing amino acids via alkyl halide alkylation of, aldol and Michael additions to a chiral Ni(II) complexes of glycine and alanine.  Discovered unusual stereodirecting features of the trifluoromethyl group. 

•         Discovered and developed the first general method for the biocatalytic resolution of b-amino acids by means of penicillin acylase.  Developed large scale biocatalytic methods for preparing enantiomerically pure fluoro-amino acids. 

Hokkaido University, Catalysis Research Center, Sapporo, Japan (6/94-8/95);  on leave from The Ukrainian Academy of Science

JSPC Research Fellow:  Studies of the transition metal-catalyzed stereoselective aldol and aza-aldol reactions of methyl isocyanoacetate with fluorinated carbonyl compounds and their imines. 

•         Developed practical methods for preparing diastereo/enantiomerically pure a-amino-b-hydroxy and a,b-diamino carboxylic acids. 

•         Discovered unusual stereocontrolling properties of perfluoroalkyl and polyfluorophenyl groups. 

Politecnico di Milano; Milan, Italy, (1/93-7/93);  on leave from The Ukrainian Academy of Science

Visiting Professor:  Design and development of new fluorine-containing chiral building blocks for efficient asymmetric synthesis of fluorinated analogs of naturally occurring compounds. 

•         Discovered a highly stereoselective epoxidation of chiral non-racemic [(4-methylphenyl)-sulfinyl]methyl fluoroalkyl ketones and applied it to the asymmetric synthesis of fluorinated nucleosides, alcohols, amines, amino and hydroxy acids. 

•         Developed asymmetric synthesis of a-trifluoromethyl amino acids via addition of chiral sulfoxide derived C-nucleophiles to the imines of trifluoropyruvic acid. 

OTHER PROFESSIONAL ACTIVITIES:

Edited works

•         Fluorine-Containing Amino Acids.  Synthesis and Properties, Kukhar, V. P.; Soloshonok, V. A. Eds., John Wiley & Sons Ltd., 1994; 

•         Enantiocontrolled Synthesis of Fluoro-Organic Compounds, Tetrahedron Asymmetry Special Issue, Guest Editors: T. Hayashi and V. A. Soloshonok, Tetrahedron: Asymmetry, 1994, 5, N 6; 

•         Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards, Tetrahedron Symposium-in-Print, # 58; Guest Editors: G. Resnati and V. A. Soloshonok, Tetrahedron, 1996, 52, N 1; 

•         Enantiocontrolled Synthesis of Fluoro-Organic Compounds, Soloshonok, V. A. Ed., John Wiley & Sons Ltd., in progress, scheduled to appear in 1999. 

•         Asymmetric Synthesis of Novel Sterically Constrained Amino Acids, Tetrahedron Symposium-in-Print # 88; Guest Editors: V. J. Hruby and V. A. Soloshonok, Tetrahedron 2001,  57, No 30. 

EDUCATION:

B.S., Organic Chemistry,

T.G.Shevchenko Kiev State University, Department of Organic Chemistry, July 1983. 

Ph.D., Organic Chemistry,

The Ukrainian Academy of Sciences, Institute of Bioorganic Chemistry, December 1987,

Thesis: "Synthesis of a-Trifluoromethyl-Containing a-Amino Acids, Amines, and a-Hydroxy Acids as Potential Inhibitors of Pyridoxal-Phosphate-Dependent Enzymes". 

Research advisor:  Professor V.P. Kukhar

AWARDS:  

•     Medal and Diploma of the Presidium of the Ukrainian Academy of Sciences for the extraordinary research achievements  (among the scientists under 35), 1988.

•     Visiting Professorship by the National Research Council (CNR), Italy, 1992. 

•     JSPS Fellowship by Japanese Society for Promotion of Science, Japan, 1993. 

•     STA Fellowship by Science and Technology Agency, Japan, 1995.