Modern Methods of Monosaccharide Synthesis from Non-Carbohydrate Sources.

Department of Chemistry, University of Florida, Gainesville, Florida 32611.
Chemical Reviews (Impact Factor: 45.66). 06/1996; 96(3):1195-1220. DOI: 10.1021/cr9403300
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    ABSTRACT: Cyclopropylbenzene was subjected to whole-cell fermentation with either Escherichia coli JM109 (pDTG601) or E. coli JM109 (pDTG602), expressing toluene dioxygenase and toluene dioxygenase - dihydrodiol dehydrogenase enzymes, respectively. The corresponding metabolites, 3-cyclopropylcyclohexa-3,5-diene-1,2-diol ( 3) and 3-cyclopropylbenzene-1,2-diol (5) have been isolated in yields of 2.5 an d1gL -1, respectively. The absolute stereochemistry correlation for 3 is provided, along with a preliminary discussion of its potential in asymmetric synthe - sis. Possible mechanistic implications are indicated for the enzymatic oxygenation through the use of calculations. Ex - perimental data are provided for all new compounds. Résumé : On a soumis le cyclopropylbenzène à une fermentation à l'aide de cellules entières d'Escherichia coli JM109 (pDTG601) ou d'E. coli JM109 (pDTG602) qui laissent écouler respectivement les enzymes dioxygénase du to- luène et dioxygénase du toluène/déshydrogénase du dihydrodiol. On a isolé les métabolites correspondants, le 3- cyclopropylcyclohexa-3,5-diène-1,2-diol (3) et le 3-cyclopropylbenzène-1,2-diol (5) avec des rendements respectifs de 2,5 g/L et 1 g/L. On présente une corrélation absolue de la stéréochimie du produit 3 ainsi qu'une discussion prélimi- naire de son potentiel éventuel en synthèses asymétriques. En se basant sur des calculs théoriques, on indique les im- plications mécanistiques possibles pour l'oxygénation enzymatique. On rapporte les données expérimentales relatives à tous les nouveaux composés.
    Canadian Journal of Chemistry 06/2002; 80(6):708-713. DOI:10.1139/v02-098 · 1.01 Impact Factor
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    ABSTRACT: A variety of global catastrophes threaten the survival of human civilization. For many of these catastrophes, isolated refuges could keep some people alive and enable them to rebuild civilization in the post-catastrophe world. This paper examines the potential importance of refuges and what it would take to make them succeed. The successful refuge will have a variety of qualities, including isolation from catastrophes and self-sufficiency. These qualities can be achieved through a variety of specific design features. We introduce the concept of surface-independence as the gold standard for refuge excellence: refuges isolated from Earth's surface will offer maximum protection against both the catastrophe itself and potentially harmful post-catastrophe populations. However, surface-independence introduces significant design challenges. We present several challenges and evaluate possible solutions. Self-sufficiency in food provision can be greatly enhanced via chemical food synthesis. The rejection of waste heat from subterranean refuges can be enhanced via building piping networks and locating refuges near running groundwater or in ice. The high cost of extraterrestrial refuges can be offset by integrating refuges into space missions with scientific, political, or commercial goals. Overall, refuges show much promise for protecting civilization against global catastrophes and thus warrant serious consideration.
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    ABSTRACT: An efficient route toward biologically relevant pentose derivatives is described. The de novo synthetic strategy features an enantioselective α-oxidation reaction enabled by a chiral amine in conjunction with copper(II) catalysis. A subsequent Mukaiyama aldol coupling allows for the incorporation of a wide array of modular two-carbon fragments. Lactone intermediates accessed via this route provide a useful platform for elaboration, as demonstrated by the preparation of a variety of C-nucleosides and fluorinated pentoses. Finally, this work has facilitated expedient syntheses of pharmaceutically active compounds currently in clinical use.
    Journal of the American Chemical Society 03/2014; 136(16). DOI:10.1021/ja502205q · 11.44 Impact Factor


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