ACS News Service Weekly PressPac: Mon May 01 16:42:03 EDT 2006

News Items in This Edition

Journalists’ Resources

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News Items in this Edition

Two New Recipes for Bird-Flu Fighter Tamiflu



A shortage of star anise is the major bottleneck in production of Tamiflu (oseltamivir), and a key reason for the shortage of Tamiflu that emerged in 2005. Tamiflu is the drug being stockpiled around the world for use in combating a possible epidemic of avian influenza. Star anise has been used for centuries to give a pungent, licorice-like flavor to Chinese foods and western favorites like Pernod and anisette. Grown mainly in China, it now provides the starting material — shikimic acid — for making Tamiflu.

Roche, which markets Tamiflu, uses about 90 percent of the world’s star anise harvest. The Roche recipe for Tamiflu not only requires a scarce starting material, but also is complicated.

Two studies, scheduled for publication in the May 24 edition of the Journal of the American Chemical Society, report development of new recipes for making Tamiflu. They are part of an effort to make more Tamiflu available at more affordable prices.

One was developed by Masakatsu Shibasaki and colleagues, at the University of Tokyo. Chemistry Nobel Laureate E. J. Corey headed the Harvard University group that developed the other synthesis. The Corey process uses abundant, inexpensive starting materials, and eliminates a potentially hazardous production step. The Corey synthesis begins with butadiene and acrylic acid (which cost only pennies per pound), has fewer steps than the Roche process, and produces twice as much Tamiflu. The discoveries also are discussed in an article in Chemical & Engineering News.

Spreading Antiseptic on Farm Fields

Journal Information

Journal: American Chemical Society

Journal Article: Corey’s Tamiflu Synthesis: “A Short Enantioselective Pathway for the Synthesis of the Anti-Influenza Neuramidase Inhibitor Oseltamivir from 1,3-Butadiene and Acrylic Acid”

Journal Article: Shibaski’s Tamiflu Synthesis: “De Novo Synthesis of Tamiflu via a Catalytic Asymmetric Ring-Opening of meso-Aziridines with TMSN3”

Pharmaceuticals and personal care products (PPCPs) have gotten a lot of attention for passing through conventional sewage treatment plants and winding up in lakes, rivers and other bodies of water. Relatively little research, however, has been done on the fate of PPCPs in the millions of tons of sewage sludge now applied to farm fields. Nationally, about 63 percent of sludge produced at sewage treatment facilities is applied to agricultural fields.

Rolf U. Halden and associates at the Johns Hopkins University Bloomberg School of Public Health in Baltimore, Md., now have begun to fill existing knowledge gaps by studying the concentrations in municipal sludge of triclocarban (TCC). This topical antiseptic is a common ingredient in many antibacterial personal care products, and primarily soaps.

In a report scheduled for the June 1 issue of Environmental Science & Technology, Halden analyzed sewage sludge at a typical activated sludge wastewater treatment plant. Researchers found that conventional sewage treatment left 79 percent of the TCC entering the plant unchanged. About 3 percent of TCC was contained in the effluent, while the majority of the TCC wound up in the sludge.

They estimate that, due to sludge recycling practices, more than 70 percent of the TCC used by consumers served by the plant is ultimately released to the environment by application of sludge to land used in part for food production. TCC in sludge, they note, can potentially accumulate in agricultural crops and may contaminate resources when it runs off or soaks into the soil.

Toward a Tastier Electronic Tongue

Journal Information

Journal: Environmental Science & Technology

Journal Article: “Partitioning, Persistence, and Accumulation in Digested Sludge of the Topical Antiseptic Triclocarban During Wastewater Treatment”

Efforts are underway to develop electronic devices that mimic the human senses of taste and smell and have useful applications. An electronic tongue, for instance, could be used in quality control in the beverage industry to ensure that each batch of soda pop or beer is uniform in flavor. Medical applications include analyzing blood and other biological fluids.

One version of an electronic tongue uses “taste buds” consisting of chemically coated beads that change color upon encountering flavor molecules that are sweet, sour, bitter or salty. In a slightly different format, Eric V. Anslyn and colleagues at the University of Texas at Austin have now taken a major step toward giving electronic tongues the fuller range of gustatory prowess of the human tongue.

Many molecules exist in a format that chemists describe as left-handed or right-handed. When most left-handed amino acid (a component of proteins) lands on the human tongue, taste buds register a bitter taste. Right-handed amino acids commonly taste sweet. In a study scheduled for the May 3 issue of the Journal of the American Chemical Society, Anslyn’s group reports the first electronic tongue with this human-like taste discrimination.

Sexy Head Turner

Journal Information

Journal: American Chemical Society

Journal Article: “Pattern-Based Discrimination of Enantiomeric and Structurally Similar Amino Acids: An Optical Mimic of the Mammalian Taste Response”

Advertising and public relations firms devote great effort to determining what turns consumers' heads and forges that critical attraction between customer and product. Scientists are trying to solve a corollary mystery in biology: What turns a sperm's head and attracts it to an egg for the encounter that results in fertilization?

Sperm are notorious for turning their microscopic heads and changing directions during their journey toward the egg. Research shows that sperm turn in response to chemical signals, a process termed chemotaxis, and even have their own olfactory receptors. Those signals may play key roles in the fertilization process. Defects in sperm chemotaxis may be a cause of infertility, and sperm chemotaxis could potentially be used as a diagnostic tool to determine sperm quality to treat male infertility.

A study scheduled for publication May 1 in Analytical Chemistry offers a new tool to probe the whats and whys of sperm chemotaxis. In a collaborative effort, the research groups headed by Milos V. Novotny and Stephen C. Jacobson at Indiana University report development and initial testing of a microfluidic device for studying sperm chemotaxis. “An advantage of the microfluidic platform over conventional chemotaxis assays is the ability to create chemical gradients with temporal and spatial stability, leading to greater repeatability in the experimental conditions,” according to the researchers.

Lessons from Magic Nano

Journal Information

Journal: Analytical Chemistry

Journal Article: “Chemotaxis Assays of Mouse Sperm on Microfluidic Devices”

A household aerosol spray called Magic Nano, which uses nanotechnology in repelling dirt and water on glass and ceramic surfaces, was recently connected to health problems. There's uncertainty over what component of the product caused the problems and whether any nanomaterials were inhaled from the spray. However, the manufacturer pulled Magic Nano from store shelves in Germany in March after nearly 100 reports of respiratory problems among consumers.

The Magic Nano affair, reportedly the first product recall in the rapidly emerging nanomaterials industry, stands as a wake-up call for hundreds of other companies hoping to steward their products to market. Chemical & Engineering News (C&EN) features the topic in a cover story appearing in its May 1 issue.

Authored by Ann M. Thayer, the article, “Chance of a Lifetime,” describes how nanomaterial producers have a rare opportunity to address environmental, health and safety concerns from the very start. Nanomaterial companies view it as a chance to “get it right from the start,” notes C&EN, the highly regarded weekly newsmagazine published by the American Chemical Society. Manufacturers are striving to anticipate and address possible health and environmental concerns, rather than playing catch-up after products are in wide use.

Taming the Toxicity of Carbon Nanotubes

Journal Information

Journal: Chemical & Engineering News

Journal Article: “Chance of a Lifetime”

More incredible claims have been made about the future of nanotechnology than perhaps any other new field of science. Big claims for the small science have included many medical applications. Among them are microscopic biosensors and drug delivery modules that bring nanodevices into direct contact with living cells in the body.

New ways of controlling the toxicity of carbon nanotubes (CNTs) and other nanostructures are critical, however, to make those visions a reality. CNTs, for instance, typically kill the cells they touch.

Researchers at the University of California in Berkeley are reporting an advance in reducing CNT toxicity. It is scheduled for publication May 3 in the Journal of the American Chemical Society. The researchers coated CNTs with gylcans, biopolymers designed to mimic the glycoproteins that make up the natural surface of cells.

Tests showed that the coated CNT were nontoxic to cells, while uncoated CNTs killed cells. “This approach for interfacing CNTs with cells should accelerate their use in biological systems,” the researchers said. Since glycans also are involved in a cell’s ability to recognize and bind, the approach also could be used to target specific CNTs to specific cells.

The work resulted from a joint interdisciplinary collaboration between research groups at Berkeley headed by Carolyn R. Bertozzi (chemistry) and Alex Zettl (physics). The lead author, X. Chen, is a graduate student jointly supervised by Bertozzi and Zettl.

Journalists’ Resources

  • Patent Watch

Anyone preoccupied with chocolates and flowers on Valentine’s Day may have missed a landmark in technological innovation. On February 14, the United States Patent and Trademark Office (USPTO) issued patent number 7,000,000. It went to Dupont senior researcher and polymer chemist John P. O’Brien for inventing polysaccharide fibers. Cotton-like material made from corn and other renewable resources, polysaccharide fibers are biodegradable and suitable for use in textiles.

USPTO received a record 406,302 patent applications in 2005, and granted 165,485 patents, including 151,079 utility (inventions), 13,395 design and 816 plant patents. The inventions being patented today are on the cusp of tomorrow’s science news.

To keep pace with some of the hottest patent activity, try the ACS’s Patent Watch publication, which focuses on important new chemistry patents. Try the RSS feed option for this website. RSS stands for Really Simple Syndication or Rich Site Summary and will deliver new content posted on the site straight to your computer, instantly and automatically. Click the orange RSS button.

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Journal Information

Journal: American Chemical Society

Journal Article: “Interfacing Carbon Nanotubes With Living Cells”