out of dozens that had listed Victor Lo, sales manager the compound as a product of Atomax Chemicals, based for sale to find out what they in Shenzhen, China, says his might know. The answers firm has only (+)-sparteine N N only deepened the mystery. in stock and is out of “We did hear about the (–)-sparteine. Atomax sup(–)-Sparteine’s shortage a few years ago, and plies lab- and industrial-scale chemical reactivity we’re not sure what caused amounts of chemicals to is attributed to the it,” says Ephraim S. Honig, most large pharmaceutical twisted conformation chief executive officer of companies around the world. of its double Strem Chemicals, based in Lo was equally puzzled by quinolizidine ring Newburyport, Mass. Honig the missing (–)-sparteine. In system, which orients said Strem would look to see fact, Lo says, it isn’t available the two amine nitrogen anywhere in China. “I do not if the company could source atoms and their lone (–)-sparteine to help make it know who the supplier(s) available to researchers again pair of electrons for outside China might be, but metal-ligand binding or I am pretty sure it is not proat a reasonable price. for hydrogen bonding. But after a couple of duced in China anymore.” weeks of checking around, A few clues in the case Honig came up empty-handed. “We heard of the missing (–)-sparteine did turn up back from a colleague that (–)-sparteine during C&EN’s investigation. The comproducers in China stopped making it, as pound has been found in two places: U.S.it was a complicated production method based chemical suppliers Sigma-Aldrich and they didn’t have a market for it,” Honig and TCI America report having small says. “But we can’t confirm if that is true. quantities available. Sigma-Aldrich sales Unfortunately, we have been unable to find representatives say they have no idea a source for (–)-sparteine or any further inwhat is happening with the (–)-sparteine formation on the reasons for the shortage.” supply chain and can’t disclose its source. Like many of those C&EN reached out to, The company lists (–)-sparteine from Honig says: “If we get any further informa$50 per 0.5 g and up, depending on the tion, we’ll get back to you.” grade and amount.
20
C&EN | CEN.ACS.ORG | APRIL 24, 2017
At TCI, R&D Manager Sriramurthy Vardhineedi has a bit more to share. In 2011, when TCI recognized the shortage, the company developed a proprietary procedure to produce kilogram quantities of high-purity (–)-sparteine as needed, Vardhineedi says. TCI is possibly the world’s only current commercial producer, he notes. (–)-Sparteine remains in high demand, Vardhineedi adds, but he points out it is expensive. TCI offers the compound at $98 per gram and up, depending on the amount. As to what happened to the supply after 2010? “We are guessing that some company decided to stop making this valuable chiral alkaloid without realizing they were the sole supplier,” Vardhineedi says. A SciFinder search for (–)-sparteine reveals how the shortage has affected chemical research. The number of papers published mentioning the compound dropped by half after the shortage, from about 60 per year in 2009 to about 30 per year in 2015; the number edged back up in 2016. For Rochester’s Weix, he remains perplexed. “I’ve asked around over the years about what happened to (–)-sparteine, and we all still wonder about it,” Weix says. “If it could be plentiful again, that would be a great service to chemistry.” ◾
®
American Chemical Society
ACS membership means …
SHAPING THE FUTURE of the chemistry enterprise. Your membership enables ACS to be on the frontlines advocating for increased funding for STEM education, R&D opportunities, science and technology jobs, and many other areas in need of support.
Learn More at
e r a h S S C A / g www.acs.or
ACS PUBLICATIONS CONGRATULATES
Carolyn Bertozzi Inducted into the 2017 National Inventors Hall of Fame for her work in Bioorthogonal Chemistry
Carolyn Bertozzi Editor-in-Chief ACS Central Science Standford University
Something new is coming in peer review. Announcing ACS Reviewer LabTM, a free online course from ACS Publications, designed to educate researchers on the fundamentals of peer review featuring six modules and interactive assessments.
acsreviewerlab.org
Brou Br ough ghtt to you by
Revelations, enlightenment, and the occasional product reincarnation. Chemistry’s dawning New Age.
