Synthetic and biosynthetic studies in the deoxyxylulose pathway.
by Feng, Ju, Ph.D., STATE UNIVERSITY OF NEW YORK COL. OF ENVIRONMENTAL SCIENCE & FORESTRY, 2010, 193 pages; 3439904

Abstract:

Terpenoids (also called isoprenoids) natural products are one of the largest groups of natural products displaying a wide variety of biological functions and potential medicinal applications. All terpenoids are biosynthetically either from the mevalonate (MVA) or from the 1-deoxy-D-xylulose (DOX) pathway.

This thesis will discuss: (1) the chemical synthesis of isotopically labeled deoxyxylulose (DOX) and its application to biosynthetic studies, and (2) the synthesis of analogs of (E)-4-hydroxy-3-methyl-2-butenyl pyrophosphate (HMBPP).

The results from feeding experiment show that multiply labeled deoxyxyluloses ([1-13C]-, [1-13C, 3-2H]-, [1- 13C, 4-2H]- and [1-13C, 3,4- 2H2]-1-deoxy-D-xylulose) provide detailed information in biosynthetic studies of terpenoids, and that all of the marine algae that were tested have the deoxyxylulose pathway as found in plants and green freshwater algae. Several chemically more stable analogs of HMBPP (a powerful immunostimulatory molecule) were synthesized.

Key Words: terpenoids, synthesis, isotope, deoxyxylulose, marine algae, (E)-4-hydroxy-3-methyl-2-butenyl pyrophosphate.

 
AdviserJose L. Giner
SchoolSTATE UNIVERSITY OF NEW YORK COL. OF ENVIRONMENTAL SCIENCE & FORESTRY
SourceDAI/B 72-04, p. , Feb 2011
Source TypeDissertation
SubjectsAnalytical chemistry; Biochemistry; Organic chemistry
Publication Number3439904
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