December 22, 2003
Volume 81, Number 51
CENEAR 81 51 pp. 39-50

ISSN 0009-2347


ORGANICS & CARBS

STU BORMAN, C&EN WASHINGTON

Exemplifying new organic reactions devised this year, Noritaka Mizuno of the University of Tokyo and coworkers developed a hydrogen peroxide-based system for converting a range of linear and cyclic olefins to epoxides with high selectivity and high atom economy [Science, 300, 964 (2003)]. It's an advance over earlier epoxidations with expensive peroxides and peracids or with environmentally polluting chlorine.

And a strategy to prepare molecular crystals with perfectly predictable architecture--by carrying out reactions on molecular crystals with porous interiors containing reagent-accessible reactive sites--was demonstrated by a group led by James D. Wuest of the University of Montreal [Angew. Chem. Int. Ed., 42, 5303 (2003)].

In organic catalysis, the first metal complexes that catalyze transamidation (amide-exchange reactions) efficiently under moderate conditions were identified by Shannon S. Stahl, Samuel H. Gellman, and coworkers at the University of Wisconsin, Madison [J. Am. Chem. Soc., 125, 3422 (2003)]. These complexes could expand the range of synthetically accessible amide-based compounds.

R. Morris Bullock and Vladimir K. Dioumaev of Brookhaven National Laboratory discovered an organometallic tungsten complex that precipitates at the end of a ketone hydrosilylation reaction--providing a new way to separate catalyst from product [Nature, 424, 530 (2003)].

In carbohydrate chemistry this year, the first enzymatic method for the synthesis of sulfur-linked oligosaccharides--an approach that could be useful for constructing thioglycosylated proteins--was developed by Stephen G. Withers and coworkers at the University of British Columbia, Vancouver [Angew. Chem. Int. Ed., 42, 352 (2003)].

A novel way to identify proteins derivatized with O-linked N-acetylglucosamine (O-GlcNAc) or O-linked N-acetylgalactosamine groups was devised by Carolyn R. Bertozzi of the University of California, Berkeley, and coworkers [Proc. Natl. Acad. Sci. USA, 100, 9116 (2003); Proc. Natl. Acad. Sci. USA, published online Dec. 1, http://www.pnas.org/cgi/content/abstract/2335201100v1]. The method--in which azides are used as handles for introducing detectable probes selectively into either type of glycosylated protein--could prove useful for high-throughput proteomics.



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