Graduation Year

2006

Document Type

Thesis

Degree

M.S.

Degree Granting Department

Chemistry

Major Professor

Kirpal S. Bisht, Ph.D.

Co-Major Professor

Abdul Malik, Ph.D.

Committee Member

Edward Turos, Ph.D.

Keywords

lipase, sophorolipid, ionic liquid, caprolactone, maltose

Abstract

New catalytic synthetic methods in organic chemistry that satisfy increasingly stringent environmental constraints are in great demand by the pharmaceutical and chemical industries. Studies over last 15 years have revealed that activity of enzymes can be increased in organic solvents rather than their natural aqueous environment. Because of their ease of use, high selectivity and environment friendliness, enzymes are enjoying increasing popularity in today's synthesis world.

Chapter 1 describes chemo-enzymatic synthesis of various glycolipid analogs. A highly regioselective macrolactonization was achieved using lipase from Candida antarctica as a catalyst. It also describes evaluation of lipases from different source and their efficiency in catalyzing the macrolactonization reaction. These analogs were synthesized using commercially available agriculture based disaccharides (maltose, lactose, cellobiose, melibiose). These glycolipid analogues have potential applications in the cosmetic industry, formulation, food production, and pharmaceutical industry.In Chapter 2, ring opening polymerization of epsilon-caprolactone in ionic liquid, [bmim][PF6] was investigated. A comparative study of ROP in different solvents (toluene, Ionic liquid, and bulk condition) was conducted. Effect of time and enzyme concentration on molecular weight and % yield was investigated. It was concluded that enzymatic ring opening polymerization of epsilon-caprolactone in ionic liquid, [bmim][PF6 ] is a very competitive and environmental friendly way of synthesizing high molecular weight polyesters.

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