Jennifer M. Mason

The chemistry of castanospermine, part II: Synthesis of deoxyfluoro analogues of castanospermine

Abstract The deoxyfluorocastanospermine compounds (4), (5), (6) and (7) were prepared from castanospermine via the novel partially protected intermediates (8), (9), (11), (13) and (17).

Acyclic phosph(on)ate inhibitors of Plasmodium falciparum hypoxanthine-guanine-xanthine phosphoribosyltransferase.

The pathogenic protozoa responsible for malaria lack enzymes for the de novo synthesis of purines and rely on purine salvage from the host. In Plasmodium falciparum (Pf), hypoxanthine-guanine-xanthine phosphoribosyltransferase (HGXPRT) converts hypoxanthine to inosine monophosphate and is essential for purine salvage making the enzyme an anti-malarial drug target. We have synthesized a number of simple acyclic aza-C-nucleosides and shown that some are potent inhibitors of Pf HGXPRT while showing excellent selectivity for the Pf versus the human enzyme.

A practical synthesis of (3R,4R)-N-tert-butoxycarbonyl-4-hydroxymethylpyrrolidin-3-ol

The title compound (+)-, required for production of transition state analogue inhibitors of enzymes involved in T-cell-dependent disorders, was synthesized in five steps. A 1,3-dipolar cycloaddition of the nitrone formed from formaldehyde and N-benzylhydroxylamine to diethyl maleate gave the racemic cis-isoxazolidine (+/-)-. Reduction of the N-O bond of this compound gave pyrrolidone (+/-)- in excellent yield. A very efficient enzymic resolution of this racemic product led to the title enantiomer (+)-. This route employs only one chromatographic purification.

The chemistry of castanospermine, part III:1,2 Castanospermine-6-phosphate, an unusual route to a novel compound

Abstract Castanospermine-6-phosphate ( 6 ) is formed efficiently from 6-chloro-6-deoxycastanospermine ( 2 ) by an unusual nucleophilic displacement of chloride by a (di)hydrogenorthophosphate anion.

Doubly Renewable Cellulose Polymer for Water-Based Coatings

A levulinoyl ester-containing cellulose polymer is introduced as a waterborne coating. Incorporation of the biomass-derived levulinic acid proceeds via an unexpected intermediate and provides the unusual feature of a cellulose derivative that is readily chemically modified. The levulinoyl-cellulose ester could be chemically manipulated, allowing it to be dispersed to generate a waterborne hydrocolloid latex. This was capable of film-formation at room temperature, and was formulated for use as a coating of high-renewable content.