Four strategies which involve synthetic elaboration of
the shikimate nucleus are discussed. Methyl shikimate was
differentially protected as the 3,4-0-cyclopentylidene ketal
and as the 5- 0- tert- butyldiphenylsilyl ether. The methyl
ester was then reduced with diisobutylaluminum hydride and
the resulting allylic alcohol was oxidized to aldehyde 47
with pyridinium...
The cyclopropene fatty acids, sterculic and malvalic, occur
naturally in a major food lipid, cottonseed oil, and have been implicated
in several physiological disorders. Rainbow trout in this
study were fed semipurified diets containing 200 or 300 ppm methyl
sterculate, and the effects on hepatic lipid and glycogen levels,
lipid...
Molecular genetic and enzymological techniques have been employed to study antibiotic biosynthesis. In this thesis, we studied the formation and modification of the nonproteinogenic amino acid enduracididine (End), which exists in two important antibiotics, mannopeptimycins (MPPs) and enduracidin.
Sequence analysis of the MPP gene cluster revealed that the product of...
Early studies on the biosynthesis of the quinoline quinone portion of
streptonigrin, 1, had suggested the intermediacy of novel aromatic amino
acids. In order to test this hypothesis, a series of compounds was synthesized
and tested for potential incorporation. [4-¹⁵N] 4-Aminoanthranilic acid,
4 5 a , [4-² H] 7-aminoquinaldinic acid,...
The two naturally occurring cyclopropene fatty acids, sterculic
and malvalic, have been synthesized. The cyclopropene ring was
made by inserting a methylene unit into an acetylenic linkage.
The synthesis of methyl sterculate was repeated using diethyl
aluminum chloride, diazomethane, and methyl stearolate.
Methyl malvalate was totally synthesized. Diethyl malonate
was...
The object of this study is the synthesis of trans-cyclopentane-1, 2-dicarboxylic acid. Five procedures designed for the synthesis of
this trans diacid are described in the literature. The procedure
devised by Perkin in 1887, Fuson and Cole in 1938, and by Brenner
in 1961 were investigated to determine which of...