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Claude S. Hudson Award in Carbohydrate Chemistry

January 8, 2007 | APPEARED IN VOLUME 85, ISSUE 2

Credit: Courtesy of Pierre Sinaÿ
Credit: Courtesy of Pierre Sinaÿ

Stu Borman

Sponsored by National Starch & Chemical

This year's Claude S. Hudson Award in Carbohydrate Chemistry goes to a researcher who has introduced and developed important new synthetic methods in the carbohydrate field, including the synthesis of a key fragment of the commercial anticoagulant heparin. The awardee is Pierre Sinaÿ, professor emeritus of organic chemistry at Pierre & Marie Curie University and at Ecole Normale Supérieure, in Paris.

Sinaÿ, 68, earned a degree in chemical engineering from Ecole Nationale Supérieure des Industries Chimiques (ENSIC), in Nancy, France, in 1961, and a Ph.D. in chemistry from the University of Nancy five years later. After research fellowships at Harvard University and Paris South University, in Orsay, France, he became an associate professor of biochemistry at the University of Orléans, in France, in 1969, and was promoted to professor in 1972. In 1986, he moved to the two Paris institutions, where he is now active as professor emeritus. Sinaÿ is a member of the French Academy of Sciences.

Sinaÿ's first postdoctoral research fellowship was in the group of Harvard professor (now professor emeritus) of biological chemistry Roger W. Jeanloz. As Sinaÿ's supervisor during his postdoctoral studies, Jeanloz notes, "I found him to be not only an excellent experimentalist but also a scientist full of new ideas in synthetic chemistry and in the application of synthetic compounds for the elucidation of biological problems."

A historical achievement in synthetic methodology was his group's discovery of glycoside formation via imidate intermediates. A subsequent modification of this technique by another researcher has become today's method of choice for the chemical synthesis of complex oligosaccharides.

Another important breakthrough by Sinaÿ and coworkers was their synthesis of a pentasaccharide fragment responsible for the antithrombotic properties of heparin. This pioneering work led to a much better understanding of heparin's drug properties by elucidating the importance of the conformational flexibility of L-iduronic acid for heparin's anticoagulant activity. To study the role of carbohydrates in different human blood types, the researchers also synthesized oligosaccharide determinants of these blood groups.

Other methods and syntheses developed and carried out by Sinaÿ and coworkers include a stereoselective method to convert glycals into anomeric spiro orthoesters; a samarium iodide-promoted ring contraction of carbohydrate derivatives; innovative syntheses of C-disaccharides as stable mimics of biologically active glycosides; and the use of di- and triisobutylaluminum for novel rearrangements of monosaccharides into carbocycles and for regioselective debenzylation. A remarkable recent follow-up was a regioselective and high-yielding double debenzylation of perbenzylated cyclodextrins, which paved the way to many new derivatives of potential utility. Among other research achievements, Sinaÿ's group has also helped advance the chemistry of anomeric organometallic species.

The award address will be presented before the Division of Carbohydrate Chemistry.



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