Endocrine What disruptor compounds screening give cocktail hits the fast bitters their lane flavor? P.22 P.40 MARCH 12, 2018 The formidable f lu Searching for new vaccines and antivirals to beat the seasonal threat P.42 Browse the largest selection of USP chemicals in the industry. 1000 USP CHEMICALS.COM from bottles to BULK Need more than just a CofA? Get Spectrum’s professionally prepared scientific documentation on most USP items. 800.772.8786 1000USPCHEMICALS.COM FileNameGoesHere:2:0 Novel Boronic Esters for Drug Discovery CombiPhos Catalysts, Inc. P.O. Box 220, Princeton, NJ 08542-0220 Phone: 609-587-6500 Fax: 609-587-6570 Website: www.combiphos.com Contents VOLUME 96, NUMBER 11 March 12, 2018 Features Cover story Outsmarting influenza Making a flu vaccine that will last 35 How to compete longer than a season is a dream 22 Endocrine assays against WuXi scientists have been chasing for go fast track Expansion of drug services giant years. Here’s how they’re working EPA ramps up efforts to create still leaves plenty of room for to make it a reality high-throughput approaches for other players in China screening chemical effects on Page 42 hormone synthesis and receptor 38 C&EN talks with pathways Angela Belcher MIT scientist harnesses biology to grow materials from the bottom up 29 Searching for cheaper malaria medicines Efforts to produce low-cost synthetic artemisinin gain momentum 40 Periodic graphics: Quote of the week The chemistry of 32 Cultural change in bitters the Midwest Andy Brunning samples the “Viruses Evonik claims success in ingredients and molecules that turning a Lilly drug plant into a lend the cocktail flavorings their are liars, pharmaceutical services facility pungency cheats, and Departments ACS News thieves.” An artist’s rendering 4 Reactions 49 ACS Comment of glycoprotein spikes 9 Concentrates 51 Inaugural hemagglutinin (orange) and 54 C&ENjobs ABCChem meeting neuraminidase (green) on —Andrew Mehle, professor, 56 Newscripts Conference builds scientific ties influenza virus particles. University of Wisconsin, around the Atlantic basin Illustration by Shutterstock Madison Page 42 53 Obituaries CENEAR 96 (11) 1–56 • ISSN 0009-2347 Reactions 1155—16th St., N.W., Washington, DC 20036 (202) 872-4600 or (800) 227-5558 EDITOR-IN-CHIEF: Bibiana Campos Seijo EDITORIAL DIRECTOR: Amanda Yarnell PRODUCTION DIRECTOR: Rachel Sheremeta Pepling SENIOR ADMINISTRATIVE OFFICER: Marvel A. Wills BUSINESS ▸ Letters to the editor career success is not unique to chemistry. NEW YORK CITY: (212) 608-6306 Michael McCoy, Executive Editor It is a stereotype that undermines all types RHic. kT uMllou l(liSne (nSioern Cioor rEredsitpoorn),d Menatr)c, RSa. Rcheeisl cEhs k(Seneanzioi r( ACdomrreinsipsotnradteivnet )A, sAsleisxtaanndt)e.r Microdroplets of valid discussions. BOSTON: (202) 236-7633 Ryan Cross (Assistant Editor). Last month a colleague and I were at CHICAGO: (917) 710-0924 Lisa M. Jarvis (Senior Correspondent). HONG KONG: 852 9093 8445 Jean-François Tremblay (Senior In a recently published interesting [ar- Pittcon to plan our 2018–20 purchases. Correspondent). LONDON: 44 1494 564 316 Alex Scott (Senior Editor). ticle] (C&EN, Nov. 20, 2017, page 16), it On day two of the expo, we were visit- WEST COAST: (315) 825-8566 Melody M. Bomgardner (Senior Editor) was mentioned that the experimentally ing a new vendor that sold a number of POLICY observed huge (up to 103 times) intensifi- products that would increase our lab’s ef- WEST COAST: (925) 519-6681 Jyllian Kemsley, Executive Editor WASHINGTON: Cheryl Hogue (Senior Correspondent) cation of chemical reactions Britt E. Erickson (Senior Editor), Andrea L. Widener (Senior Editor) in a dispersion of droplets SCIENCE/TECHNOLOGY/EDUCATION in a continuous phase has WASHINGTON: Lauren K. Wolf, Executive Editor, Deputy Editorial Director Celia Henry Arnaud (Senior Editor), Stuart A. Borman (Senior Correspondent), not received any explana- Matt Davenport (Senior Editor, Multimedia), Carmen Drahl (Senior Correspondent), Kerri Jansen (Assistant Editor, Multimedia), tion. The goal of this letter Tien M. Nguyen (Assistant Editor). is to provide one. BERLIN: 49 30 2123 3740 Sarah Everts (Senior Editor). BOSTON: (973) 922-0175 Bethany Halford (Senior Editor). An intensified reac- CHICAGO: (847) 679-1156 Mitch Jacoby (Senior Correspondent). tion can occur when the WEST COAST: (626) 765-6767 Michael Torrice (Deputy Executive Editor), (202) 815-6827 Sam Lemonick (Assistant Editor) mass-transfer coefficient JOURNAL NEWS & COMMUNITY between the continu- (510) 768-7657 Corinna Wu (Senior Editor) ous phase and droplets (651) 447-6226 Jessica H. Marshall (Associate Editor) becomes large enough. ACS NEWS & SPECIAL FEATURES This can happen for Linda Wang (Senior Editor) nano-range droplets. In- EDITORIAL PROJECTS EDITOR: Jessica Morrison deed, the mass-transfer AUDIENCE ENGAGEMENT EDITOR: Dorea I. Reeser coefficient is given by the EDITING & PRODUCTION well-known expression Sabrina J. Ashwell (AKsimsisbtearnlyt RE.d Bitoryrs),o Cnr, aEigxe Bceutttiveen hEaduitsoern (Associate Editor), kR/D ~ (RU/v)1/2(v/D)1/3, Melissa T. Gilden (Assitant Editor), Taylor C. Hood (Assistant Editor), Manny where R is the radius of I. Fox Morone (Associate Editor), Alexandra A. Taylor (Assistant Editor) the droplet, U its velocity, C&EN MEDIA PRODUCTION LAB v the kinematic viscosity, Robert Bryson, Creative Director, Head of Media Production Lab Tchad K. Blair, Head of UI/UX Design D the diffusion coefficient, Robin L. Braverman (Senior Art Director), Luis A. Carrillo (Web Production Manager), Ty A. Finocchiaro (Senior Web A ssociate), Yang H. Ku and k the mass-trans- (Art Director), William A. Ludwig (Art Director), Kay Youn (Art Director) fer coefficient. Hence C&EN BRANDLAB k ~ R–1/2U1/2v–1/6D2/3. Rajendrani Mukhopadhyay, Executive Editor The above equation re- Jeff Lee (Senior Editor), Kirsten Dobson (Marketing Manager) veals that in the nano range SALES & MARKETING Stephanie Holland, Assistant Director, Advertising Sales & Marketing (very small R), the mass Natalia Bokhari (Advertising Operations Manager), transfer is increased in Sondra Hadden (Senior Marketing Manager), Joyleen SanFe- liz Parnell (Advertising Operations Associate), Quyen Pham (Lead comparison to the non-na- Generation Associate), Ed Rather (Recruitment Advertising Prod- uct Manager), Ben Smith (Audience Development Manager), no range, and this can Kierra Tobiere (Recruitment Sales & Marketing Associate) indeed increase the rate of the chemical ficiency. The vendor shared a large booth ADVISORY BOARD reaction in droplets. with its sister company specializing in Deborah Blum, Raychelle Burks, Jinwoo Cheon, Kendrew H. Colton, François- Eli Ruckenstein lab-themed gifts. There were a few plush Xavier Coudert, Cathleen Crudden, Gautam R. Desiraju, Paula T. Hammond, Matthew Hartings, Christopher Hill, Yan Liang, Javier García Martínez, Peter Williamsville, N.Y. “lab rat” toys displayed. One appeared to Nagler, Daniel García Rivera, Anubhav Saxena, Dan Shine, Michael Sofia, William Tolman, James C. Tung, Jill Venton, Helma Wennemers, Geofrey K. Wyatt, be female and wore a white lab coat with Deqing Zhang Products perpetuating “Flirty” embroidered on it. PuTbhloismheads bMy. tChoen AneMllEy RJrI.C, EAxNe cCuHtivEeM DIiCreAcLto Sr O&C CIEEOTY stereotypes Here was a toy that perpetuated the H) gender bias stereotype. There was also a T Brian D. Crawford, President, Publications Division O B EDAICTSO RBIoAaLrd B oOf DAiRreDc:t oNrisc oClhea Sir. JSoahmnp Es.o And (aCmhasi,r ), Scievxil- braigshetds dviisoclraitmioinn atthiaotn t iask ae sc ommanmyo n TTe-sshtyir)t bweiitnhg atnooldth beyr af emmaallee l laabb r raatt t (hnaatm sheed OVE ( ACS President Peter K. Dorhout, Cynthia J. Burrows, forms. How does it begin? How can we was overreacting. It was a double enten- GR Jerzy Klosin, Julia Laskin, John Russell LE build more positive outcomes? The arti- dre because Testy was holding a bubbling O C CopCyraingahdt i2an0 1G8S, TA mReegri.c Naon. CRh1e2m75ic7a1l 3S4o7ci ety cle “Confronting Sexual Harassment in flask. Flirty was not an outlier; she was a HY T Volume 96, Number 11 Chemistry” from the Sept. 18, 2017, issue trend. I reviewed the company’s website O R O brought to light the different experiences and found kid-sized T-shirts emblazoned D between genders in chemistry. The idea with Flirty proclaiming, “Future Scientist” DIT: E that women use their sexuality to leverage (or “Biologist” or “Physicist”). The male R C 4 C&EN | CEN.ACS.ORG | MARCH 12, 2018 Expertise on every level to craft science and technology solutions in life science Trusted Analytical Products Pioneering Lab Water Solutions State-of-the-Art Lab & Production Materials Expert Pharma & Biopharma Manufacturing & Testing Services Tailored Pharma & Biopharma Raw Material Solutions Proven Preparation, Separation, Filtration & Testing Products The life science business of Merck KGaA, Darmstadt, Germany operates as MilliporeSigma in the U.S. and Canada. MilliporeSigma, the vibrant M, Milli-Q, Millipore, SAFC, BioReliance, MilliporeSigma has brought together the world‘s Supelco and Sigma-Aldrich are trademarks of Merck KGaA, Darmstadt, Germany or its affiliates. All other trademarks are the property of their leading Life Science brands, so whatever your life respective owners. Detailed information on trademarks is available via publicly accessible resources. science problem, you can benefit from our expert products and services. © 2018 Merck KGaA, Darmstadt, Germany and/or its affiliates. All Rights Reserved. To find out how MilliporeSigma can help you work, visit SigmaAldrich.com/advancinglifescience #howwesolve LSCI17UKLO0737_C&EN_Advert_MilliporeSigma.indd 2 19/12/2017 17:51 rats are Matt (founder’s son), Gym, and of gas chromatography/mass spectrome- Introducing our podcast, Slacker (I recommend renaming this one). try with injections made with solid-phase Why not rename the female rats Testy, microextraction GC syringes could give Flirty, and Petri as Marie, Shirley, and bibliographic science a handle on (1) the Rosalind? animal source of the vellum; (2) the Viewing these products made me think age of the vellum, both when first made twice about doing any business with either and later after having been written company. The strongest power I have is on; and (3) possibly the methods used as a consumer, and I will choose to forgo in the vellum preparation. Currently, purchasing their products because of the 14C radiocarbon dating has been applied latent sexism. I recognize the irony of me to determine vellum age (as the source being labeled as “overreacting” about a toy was once living), but this involves some Tune in every month for by the same vocal minority that dismisses skin destruction to obtain a sufficient harassment claims. But I also see this as sample. And identifying the animal used the chemistry stories a clear example of the hidden sexism that for the vellum by microscopic analysis of is so ingrained in our profession that the skins to detect original hair follicles can that matter most. joke has been monetized in an unironic sometimes pose problems in handling an- manner. I struggle even to put my full cient manuscripts. The method of vellum name to this letter for fear of negative preparation, such as treatment with alkali Subscribe now on iTunes, Google Play, comments like “Just get over it” and “It’s to remove residual hair (left in some cas- SoundCloud, or TuneIn. just a joke.” However, I will take my in- es) and soften the skins, is likely based spiration from the Feb. 15 ACS webinar mainly on the known practices used in (“Sexual Harassment in the Sciences: their usual methods of preparation but is Steps Forward”) that encouraged, “I’ll not chiefly guesswork. be silent.” Wishing them continued success in Dorothy Colegrove further developing and employing their Anchorage method, which I think could be of huge significance in handling old paper and, I Aromas and chemistry am convinced, likely vellums. Thomas F. Spande I found the article by Carrie Arnold in the Bethesda, Md. Nov. 27, 2017, issue of C&EN (page 19) on the work of graduate student Bembibre Carrie Arnold credits the first aroma and her supervisor Strlič in identifying the wheel to Ann Noble “in the 1980s” with odors released by aging paper to be stim- flavor wheels for other products, like ulating and possibly of importance in an- beer, coming later. The actual date of other area: possible odorous and nonodor- Noble’s aroma wheel seems to be 1984, ous compounds emanating from vellum five years after the publication of the beer manuscripts. Even after paper was a com- flavor wheel by a subcommittee of the mon article of commerce, some important American Society of Brewing Chemists (J. documents continued to be produced by Am. Soc. Brew. Chem. 1979, DOI: 10.1094/ scribes writing on the specially treated ASBCJ-37-0047). The wheel itself is on skins chiefly of calves, young goats, and page 51. lambs, called vellums, in general. Roger Barth Perhaps their use of the combination West Chester, Pa. Correction ▸ March 5, page 3: In the news story on the Chematica computer program, the description of how the program’s 50,000 synthetic rules were developed was incom- plete. The rules were developed on the basis of reactions published in the chemical literature and insights from organic chemists on the team. Also, the story incorrectly stated that only one of the eight tested target molecules did not have a previously published synthetic route. In fact, two of the targets had not been synthesized before. The story also failed to point out that a contender to Chematica—ChemPlanner from John Wiley & Sons—will be integrated into SciFindern, which is a product from CAS, a division of the American Chemical Society. Finally, K. C. Nicolaou’s thoughts on how the program could improve lab productivity were described inaccurately. The sentence should have read: “ ‘These encouraging results should serve as a spark for another advancement in organic synthesis,’ says K. C. Nicolaou, a synthetic chemist at Rice University, adding that Chematica could increase speed and productivity in chemistry labs, especially if paired with automated synthesis machines.” 6 C&EN | CEN.ACS.ORG | MARCH 12, 2018 Every shade of brilliance for creative science and technology solutions in life science Proven Preparation, Separation, Filtration & Testing Products Expert Pharma & Biopharma Manufacturing & Testing Services State-of-the-Art Lab & Production Materials Trusted Analytical Products Pioneering Lab Water Solutions Tailored Pharma & Biopharma Raw Material Solutions The life science business of Merck KGaA, Darmstadt, Germany operates as MilliporeSigma in the U.S. and Canada. MilliporeSigma, the vibrant M, Milli-Q, Millipore, SAFC, BioReliance, MilliporeSigma has brought together the world‘s Supelco and Sigma-Aldrich are trademarks of Merck KGaA, Darmstadt, Germany or its affiliates. All other trademarks are the property of their leading Life Science brands, so whatever your life respective owners. Detailed information on trademarks is available via publicly accessible resources. science problem, you can benefit from our expert products and services. © 2018 Merck KGaA, Darmstadt, Germany and/or its affiliates. All Rights Reserved. To find out how MilliporeSigma can help you work, visit SigmaAldrich.com/advancinglifescience #howwesolve LSCI17UKLO0737_C&EN_Advert_MilliporeSigma.indd 3 19/12/2017 17:51 ▸ From the web their distinctive odor, which I find mildly before modern manufacturing all but elim- pleasant. inated compounding from everyday phar- Re: How science may ken osborn macy practice. The favorite aroma for most old-timers? Tincture of benzoin, of course! help us smell the past Here at the American Institute of the His- Greg Higby tory of Pharmacy (UW Madison School of Readers commented on the intersection of Pharmacy) we routinely open up one or Join the conversation. smell and chemistry online. two of our artifact cabinets so that visitors facebook.com/CENews cenm.ag/smellpast can experience “that old drugstore smell.” This experience is especially moving for @cenmag Interesting work, but establishing a list of pharmacists over the age of 70, who re- @cenmag vocabulary words is only one piece of the member how pharmacies used to smell puzzle. These metaphors or associations will differ from one person to another depending upon our individual experi- How to reach us ences and associations. It is unlikely that we will be able to recreate the emotions associated with odors by historical figures Chemical & Engineering News Subscriptions because, as pointed out in the article, our Letters to the Editor Send all new and renewal subscriptions and requests for subscription rates to ACS, Dept. L-0011, Columbus, OH odor experiences and associations will be ▸ Our e-mail address is [email protected]. 43268-0011. very different. ▸ Our fax number is (202) 872-8727. Nick Sauer ▸ Comments can be left at cen.acs.org. ▸ Changes of address, claims for missing issues, sub- scription orders, status of records, and accounts should ▸ Or you can send your letter to: be directed to Manager, Member & Subscriber Services, As a retired lab rat from an environ- C&EN Editor-in-Chief ACS, P.O. Box 3337, Columbus, OH 43210; telephone mental lab that included an odor panel 1155—16th St., N.W. (800) 333-9511 or (614) 447-3776; or send an e-mail to rate drinking water samples, I find Washington, DC 20036 to [email protected]. the use of odor profiles through the ▸ Letters should generally be 400 words or fewer and should include the writer’s full name, address, and home Advertising human-instrument combination fasci- telephone; letters and online comments may be edited ▸ For advertising information and opportunities, go to nating. At my home library I have a few for purposes of clarity and space. Because of the heavy cen.acs.org/advertise. For advertising rates, contact books that date to the late 19th century volume of mail received at C&EN, writers are limited to one Stephanie Holland at [email protected]. For the editorial and can detect and distinguish them by letter in a six-month period. calendar, contact Kirsten Dobson at [email protected]. talks with Priestley Medalist GERI RICHMOND Meet the recipient of this year’s Priestley Medal, Geraldine Richmond. Richmond has been recognized for her pioneering contributions to our understanding of the molecular properties of liquid surfaces and her extraordinary service to chemistry on a global level. Visit the ACS Theater at the ACS spring national meeting to learn more and receive an autographed copy of C&EN. ▸ Tuesday, March 20 11 AM–noon ▸ Ernest N. Morial Convention Center New Orleans ACS Theater; ACS booth 8 C&EN | CEN.ACS.ORG | MARCH 12, 2018
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