December 2013 NUCLEUS 11-7-2013Aa6web
DED UN 18 O 98 F
http://www.nesacs.org
N
Y
O
T
R
E I
T
H C
E N O A E S S S L T A E A C R C I N S M S E E H C C TI N December 2013 Vol. XCII, No. 4 O CA N • AMERI
Monthly Meeting Summer Scholar Report A Medicinal Chemistry Symposium at Asymmetric Mannich Reactions via Pseudoephenamine Genzyme/Sanofi in Waltham Glycinamide Enolization. By Claire S. Harmange, Ian B. Seiple, Robin J. Sussman, Andrew G. Myers Photos and Reports NAS Biographical from NERM Memoirs By Morton Z. Hoffman By Michael Filosa Report from New Haven: Meeting of the Board of Directors of NERACS Morton Z. Hoffman, NESACS Representative to the NERACS Board [[email protected]] The Board of Directors of the North- east Region of the ACS, Inc. (NER- ACS) met on Saturday, October 26, 2013, in the Omni New Haven Hotel on the occasion of the Northeast Regional Meeting (NERM 2013). The NERACS Board consists of its Chair (Julianne Smist, Springfield College), Vice Chair (Richard Cobb, Eastman Kodak, retired), Secretary (Christopher Masi, Westfield State University), Treasurer (Wayne Jones, SUNY Bing- hamton), and representatives from the Doris Lewis (Suffolk University), flanked by Sharon Palmer (Amherst Regional High following local sections: Binghamton, Marinda Wu (ACS President) at left and Julie School), flanked by Marinda Wu (ACS Presi- Central Massachusetts, Central New Smist (NERACS Chair), receiving the 2013 E. dent) at left and Julie Smist (NERACS Chair), Ann Nalley Northeast Region Award for Volun- receiving the 2013 Division of Chemical Educa- York, Connecticut Valley, Cornell, teer Service to the ACS. tion Northeast Region Award for Excellence in Corning, Eastern New York, Green High School Teaching. Mountain, Maine, Mid-Hudson, New the present time, any income above (Photos by M. Z. Hoffman) Haven, Northeastern, Northern New expenditure for a NERM is shared in a financial balance sheet for the meeting York, Penn-York, Rhode Island, 40/60 ratio between NERACS and the should be in positive territory. Rochester, Western Connecticut, West- hosting local section. NERM 2015 will be held at Ithaca ern New York. Cobb expressed concern about the College, June 10-13, with Akiko Fill- In addition to executive officers paucity of nominations for the region continued on page 12 Smist, Cobb, and Masi, the following awards that are presented at NERM; in local section representatives were pres- fact, some awards cannot be given ent at the meeting: Willem Leenstra because the number of nominations (Green Mountai n), Mark Zell (Rhode does not reach the stipulated minimum. Island), Akiko Fillinger (Cornell), He asked the representatives of the Richard Hartmann (Rochester), local sections to urge their officers and Mitchell Bruce (Maine), Kenneth members to be active in the nomina- White and Jefferson Chin (New tion process. Inasmuch as there will be Haven), Morton Hoffman (Northeast- no NERM in 2014, there is now ample ern). Also in attendance were Thomas time for nominations to be generated Gilbert (ACS District I Director) and for the 2015 cycle of the following Michelle Stevenson (ACS staff liaison Northeast Region awards: Achieve- to NERM). ments in the Chemical Sciences, The Board elected Richard Cobb Excellence in High School Teaching, and Willem Leenstra as Chair and Vice Volunteer Service to the ACS, Advanc- Chair, respectively, for two-year terms ing Diversity in the Chemical Sci- (2014-15). It voted by acclamation its ences. appreciation for the service Julianne It was reported that as of that Smist provided as Chair for six years morning, more than 850 registrations from the time of the incorporation of had been received for NERM 2013; NERACS. The terms for the current over 480 oral and poster presentations Secretary and Treasurer run through were included in the program. There 2014. were 140 undergraduate research It was announced that the assets in posters, four high school student the NERACS Treasury are close to posters, and 27 exhibitors at the meet- $50,000; when they reach that level, ing. Although the room quota had not discussions will take place concerning been met at the Omni Hotel, which the long-term use of those funds. At will result in some penalty, overall the
2 The Nucleus December 2013 The Northeastern Section of the American Chemical Society, Inc. Contents Office: Anna Singer, 12 Corcoran Road, Burlington, MA 01803 (Voice or FAX) 781-272-1966. e-mail: secretary(at)nesacs.org Report from New Haven: NERACS ______2 NESACS Homepage: Meeting of the Board of Directors http://www.NESACS.org Officers 2013 Chair NESACS SE-MA Area Event______4 Liming Shao By Morton Z. Hoffman 158South Great Road Lincoln, MA 01773 limingshao(at)comcast.net Monthly Meeting ______5 shao(at)fas.harvard.edu 781-518-0720 A Medicinal Chemistry Symposium “Innovative Treatments for Chair-Elect Unmet Medical Needs” at Genzyme/Sanofi in Waltham, MA Catherine Costello Boston University School of Medicine 670 Albany Street, room 511 Report from New Haven: NERM ______6 Boston, MA 02118-2646 by Morton Z. Hoffman cecmsms(at)bu.edu Immediate Past Chair Ruth Tanner NAS Biographical Memoirs 7 Olney Hall 415B ______Lowell, MA 01854 By Michael P. Filosa University of Mass Lowell Ruth_Tanner(at)uml.edu 978-934-3662 Summer Scholar Report ______8 Secretary: Asymmetric Mannich Reactions via Pseudoephenamine Glycinamide Enolization Michael Singer Sigma-Aldrich By Claire S. Harmange, Ian B. Seiple, Robin J. Sussman, Andrew G. Myers 3 Strathmore Rd, Natick, MA 01360 774-290-1391, michael.singer(at)sial.com Photos from NERM 10 Treasurer: ______James Piper 19 Mill Rd, Harvard, MA 01451 978-456-3155, piper28(at)attglobal.net Cover: Pictured at the first SE-MA NESACS area event held at UMass - Dart- Auditor: mouth on October 3, 2013 from L-R are Morton Hoffman, Robert Lichter, Jack Anthony Rosner Driscoll, Madeleine Jacobs, Ruth Tanner and Liming Shao. (Photo courtesy of Archivist Tim Frigo M. Z. Hoffman) Trustees: Peter C. Meltzer, Esther A. H. Hopkins, Editorial Deadlines: Michael E. Strem February 2014 Issue: December 15, 2013 Directors-at-Large March 2014 Issue: January 15, 2014 David Harris, Stephen Lantos, James Phillips, Ralph Scannell, Mary Burgess, John Burke Councilors Alternate Councilors Term Ends 12/31/2013 Alfred Viola Mark Froimowitz Michael Singer Sophia R. Su Robert Lichter Kenneth C. Mattes Mary Shultz Tim Frigo Leland L. Johnson, Jr. Mukund Chorghade Term Ends 12/31/2014 Katherine Lee C. Jaworek-Lopes The Nucleus is published monthly, except June and August, by the Northeastern Section of the American Michael P. Filosa Lawrence Scott Chemical Society, Inc. Forms close for advertising on the 1st of the month of the preceding issue. Text Doris Lewis Andrew Scholte must be received by the editor six weeks before the date of issue. Morton Z. Hoffman Raj Rajur Editor: Michael P. Filosa, Ph.D., 18 Tamarack Road, Medfield, MA 02052 Email: Patrick Gordon John Podobinski Mary Burgess Stuart Levy filosam(at)verizon.net; Tel: 508-843-9070 Term Ends 12/31/2015 Associate Editors: Myron S. Simon, 60 Seminary Ave. apt 272, Auburndale, MA 02466, Catherine E. Costello Marietta Schwartz Mindy Levine, 516-697-9688, mindy.levine(at)gmail.com Ruth Tanner JerryJasinski Board of Publications: Mary Mahaney (Chair), Vivian K. Walworth, James Phillips Dorothy J. Phillips Stephen Lantos Michaeline Chen Norton P. Peet Business Manager: Karen Piper, 19 Mill Rd., Harvard, MA 01451, Tel: 978-456-8622 Jackie O’Neil Wilton Virgo Advertising Manager: Vincent J. Gale, P.O. Box 1150, Marshfield, MA 02050, All Chairs of standing Email: Manager-vincegale(at)mboservices.net; Tel: 781-837-0424 Committees, the editor Contributing Editors: Morton Hoffman, Feature Editor; Dennis Sardella, Book Reviews of THE NUCLEUS, and Calendar Coordinator: Michael P. Filosa, email: Michael.filosa(at)verizon.net the Trustees of Section Photographers: Morton Hoffman and James Phillips Funds are members of the Board of Directors. Any Proofreaders: Donald O. Rickter, Vivian K. Walworth, Mindy Levine Coun cilor of the American Chemical Soci- Webmaster: Roy Hagen ety residing within the section area is an ex Copyright 2013, Northeastern Section of the American Chemical Society, Inc. officio member of the Board of Directors. The Nucleus December 2013 3 “Everything You Always Wanted to NESACS Know about ACS, But Were Afraid to 2013 NESACS Golf Sponsors Ask” at the first Southeastern Massa- chusetts (SE-MA) area event organized LSNE Lyophilization Services of NE SE-MA Area by the Subsection Task Force (STF). Strem Chemical Among those attending were former Litman Gerson Event and current NESACS members from Sage Chemical industry and academia, nonmember Davos at UMass Dartmouth – chemists and teachers from the area, Prime Organics October 3, 2013 representatives from the Rhode Island Brian O-Reilly, LLP, Patent Litigation Local Section, and guests. The meet- By Morton Z. Hoffman ing also attracted a significant number Johnson Matthey of UMD faculty and students. IRIX Pharmaceuticals Cambridge Major O’Conner Carnathan and Mack, LLC Edelstein and Co. Chengda - Social Hour Sponsor
engage members in areas that are remote from our Boston/Cambridge and environs core in which almost all Emmanuel Ojadi with MadeleineJacobs the Section’s activities take place, specifically, SE-MA (Barnstable, Bris- MadeleineJacobs meets with UMD Students Approximately 80 people came to the tol, Dukes, Nantucket, and Plymouth University of Massachusetts Dart- The purpose of the meeting was to Counties) and New Hampshire (NH). mouth (UMD) on Thursday, October 3, begin the process of exploring the fea- At the present time, STF has the fol- to hear Madeleine Jacobs, ACS Execu- sibility of establishing subsections lowing membership: Morton Hoffman tive Director and CEO, speak on within NESACS to help connect and (Boston University), Ruth Tanner (University of Massachusetts Lowell), Robert Lichter (Merrimack Consult- ants), Jack Driscoll and Jennifer Maclachlan (PID Analyzers), Robert Howard (Weeset Advisors), Jerry Jasinski (Keene State College) and Gary Weisman (University of New Hampshire). The meeting began with a recep- tion with light refreshments that was sponsored by the UMD Department of Chemistry and Biochemistry, which is chaired by Emmanuel Ojadi; he and Liming Shao, NESACS Chair, gave welcoming remarks, and Provost Mohammad Karim brought greetings from the administration of the Univer- sity. Jack Driscoll then spoke about the purpose of the event, described the many activities that NESACS has sponsored and cosponsored in SE-MA over the past several years, and pro- vided a blueprint for the future. Robert Lichter introduced Ms. Jacobs, who spoke about the vision (“Improving people’s lives through the continued on page 12
4 The Nucleus December 2013 Abstract Monthly Meeting Title: A Winding Journey of Medicinal The 936th Meeting of the Northeastern Section of the American Chemistry toward the Discovery of a Potent, Selective, and Orally Bioavail- Chemical Society able Histamine H3 Receptor Antago- Organized by the Medicinal Chemistry Group of the nist for Cognitive Impairment: From a Northeastern Section of the American Chemical Society Biological Concept to a Development Candidate Sponsored by Sanofi Cognitive impairment or deficit is an Symposium inclusive term to describe any charac- teristic that acts as a barrier to the cog- Innovative Treatments for Unmet Medical Needs nition process. More than 16 million December 12, 2013 people in the United States are living Genzyme Corporation/Sanofi with cognitive impairment. Currently, 153 Second Avenue, Waltham Massachusetts 02451 no cognitive impairment drugs or other Northeastern Conference Room treatments are specifically approved by the Food and Drug Administration 3:00 pm Refreshments (FDA), although physicians sometimes 3:15 pm Welcome prescribe cholinesterase inhibitors. Raj (SB) Rajur, Program Chair, CreaGen Biosciences, Inc., These, however, aren’t recommended Woburn, MA for routine treatment because they 3:20 pm Introductory Remarks don’t appear to provide lasting benefit. H3 receptor (H3R), a pre-synaptic Norton P. Peet, Director of Chemistry, Microbiotix, Worcester, MA GαI/O protein-coupled auto-receptor, 3:30 pm Barry Toure, Novartis Institute for Biomedical Research, Boston is widely expressed in the mammalian 4:15 pm John Williams, Senior Scientist, Microbiotix, Inc., Worcester, MA brain, particularly in areas involved in “Novel Inhibitors of the Pseudomonas Type Three Secretion System” cognitive processes and arousal, such 5:00 pm TBA as the cerebral cortex, hippocampus, basal ganglia, and hypothalamus. 6:00 pm Social Hour Blockade of H3R with selective antag- 6:45 pm Dinner onists/ inverse agonists is hypothesized 7:45 pm Keynote Presentation to increase the synthesis and release of Introduction: David Aldous, Head of Boston LGCR, Sanofi, histamine and other neurotransmitters Waltham, MA involved in alert and cognitive func- tions. We are interested in discovery Speaker: continued on page 12 Zhongli Gao, Genzyme-Sanofi, Waltham, MA A Winding Journey of Medicinal Chemistry toward the Discovery of a Potent, Selective, and Orally Bio-available Histamine H3 Directions to Genzyme-Sanofi Receptor Antagonist for Cognitive Impairment: From a Biological From North or South 95/Rt 128 Concept to a Development Candidate South. YOU MUST REGISTER IN ADVANCE, BUT THERE IS NO REGIS- Take Exit 27B/Winter Street. Follow TRATION FEE TO ATTEND THE SYMPOSIUM; the signs for Second Avenue (stay in DINNER RESERVATIONS ARE REQUIRED. right lane). Take a right after the Embassy Suites Hotel onto Second THE PUBLIC IS INVITED Avenue. Go past Costco on the right Dinner reservations should be made no later than noon, Thursday, December At ADP take a right between ADP 5th, 2013. Reservations are to be made using PayPal: http:// garage and ADP offices. (There is a acssymposium.com/paypal.html. Select pay with credit or debit card option sign directing you to Genzyme). Pro- and follow the additional instructions on the page. Members, $30; Non-mem- ceed about 100 feet. Genzyme will be bers, $35; Retirees, $20; Students, $10. Reservations for new members and for on the right. additional information, contact the secretary, Anna Singer, at (781) 272-1966 Link to directions: between 9am and 6pm or e-mail at [email protected]. Reservations not http://www.genzyme.com/~/media/Fil cancelled at least 24 hours in advance must be paid. es/GenzymeCorp/PDF/directions_walt ham.pdf u
The Nucleus December 2013 5 Report from New Haven: NERM 2013 Morton Z. Hoffman, Chair, NERM Committee [[email protected]] The New Haven Local Section hosted the ACS Northeast Regional Meeting (NERM 2013) on October 23-26 at the Omni New Haven Hotel. With more than 850 registrants making over 480 oral and poster presentations (includ- ing 140 undergraduate research posters, and four high-school student posters) as well as 27 exhibitors, the meeting was an exciting professional event with ACS President Marinda Wu and Classic New England Immediate Past President Bassam Shakhashiri in attendance. Forty-three Stefan Zajonc (Karlsruhe University of separate sessions, spanning a broad Michelle Stevenson (ACS), staff liaison to Education). NERM, with Jefferson Chin (Bristol-Myers spectrum of the chemical sciences, The members of the NESACS Squibb), General Co-Chair of NERM. were packed into three days of pro- German Exchange Steering Committee gramming. The full program is avail- who attended NERM were Morton 3:00-3:10 p.m. Intermission able online at
6 The Nucleus December 2013 National Academy of Sciences - Biographical Memoirs http://www.nasonline.org/publications/biographical-memoirs/online-collection.html By Michael P. Filosa While searching for a photo of James their long friendship. Another is the memoir for Margaret Flack Norris (1871-1940) for the Woodward and James Conant Mead. November Nucleus, I came across his were influenced at Harvard by E. P. Florence Rena Sabin was born in biographical memoir on the website of Kohler (1865-1938). Kohler’s memoir Central City, Colorado. Her father the National Academy of Sciences was written by James Conant in 1952. abandoned the idea of a medical career (NAS). This memoir was written by Conant in turn was memorialized by to become a mining engineer, leaving John D. Roberts and was presented to his student Paul D. Bartlett. Bartlett the family farm in Vermont for Col- the Academy in 1974, a scant(!) 34 was an immensely influential physical orado in 1860, where he married a years after his death. organic chemist. His memoir was writ- school teacher from Blackhawk, Col- The NAS was founded in 1863 by ten by Frank Westheimer and begins: orado in 1868. Florence’s mother died 50 of the most prominent scientists in “Paul Bartlett was one of the great when she was young and she and her the United States, and its initial charter chemists of the twentieth century. His sister were sent back east to live with was signed by Abraham Lincoln. It is a research and teaching were in the area their uncle and grandparents in Illinois tradition that each of its members be of physical-organic chemistry, and he and Vermont. Florence ultimately memorialized in a memoir to the Acad- dominated that field for perhaps four attended Smith College with her sister. emy written by a peer (or two). decades. He wasn’t old enough to be There she developed her interest in sci- These memoirs are a treasure among the earliest practitioners; that ence. trove of the history of science. The honor is shared among Arthur Lap- Florence initially taught school in sole weakness is that they are posthu- worth, A. Hantzsch, C. K. Ingold, and Denver and then was an assistant in mous and not necessarily, very timely. L. P. Hammett. But Bartlett created a zoology at Smith before working at the However, they are quite thorough and school of physical-organic chemistry Marine Biological Laboratories in a good overview of the scientists, com- that sparked a revolution in the way Woods Hole. However, her ultimate plete with a detailed listing of their organic chemistry is taught and prac- ambition, once she had saved some major works. ticed throughout the world.” money, was to attend Johns Hopkins During my school years, I was If the history of Harvard’s great Medical School, which was founded in always intrigued with stories about chemists and the development of Har- 1893 with the stipulation by its bene- great scientists. Dan Kemp would talk vard chemistry are not your interest, factors that women should be admitted extensively about his thesis advisor, R. you can read the memoirs of A. C. as well as men. B. Woodward, and his works. Those Cope, John Sheehan or George Buchi Florence became a protégé of Dr. stories about Woodward (1917-1979) of M.I.T. Sheehan’s memoir was writ- Franklin Paine Mall, the school’s first and also Gilbert Stork were very influ- ten by E. J. Corey and John D. Professor of Anatomy. She flourished ential in my decision to pursue syn- Roberts. You can also read the memoir under the guidance of Dr. Mall and his thetic organic chemistry as a career. of William Barton Rogers, founder of philosophy of education. Her inde- Woodward’s memoir was written M.I.T., or the memoir of Vannevar pendent work won much acclaim and by Elkan Blout (with assistance from Bush, written by Jerome Wiesner. she was appointed in 1917 Professor of Frank Westheimer) and was published Edwin Land’s memoir was written Histology, the first woman to obtain a in 2001, a “scant” 22 years after his by his biographer, Victor K. McElheny. full professorship in the Johns Hopkins death. The memoir is a far more succinct Medical School. The memoirs are often glowing: summary of Land’s life than the book. Other non-chemistry memoirs of “Robert Burns Woodward was the pre- The best way to find a memoir is note is the glowing memoir written eminent organic chemist of the twenti- to use the search engine. I became about Louis Agassiz, one of the 50 eth century. This opinion is shared by intrigued with who was the first female founding members of the NAS. I was his colleagues, students and by other member of the NAS. The search also fascinated to find the memoirs for distinguished chemists.” engine did not provide a way to find the two protagonists of the “Dinosaur Blout includes lengthy commen- this person, but Google gave me a Wars:” Edward Drinker Cope and Oth- taries from Sir Derek Barton, Roald quick answer, Florence Rena Sabin niel Charles Marsh. Their biographers Hoffman and Albert Eschenmoser in (1871-1953), inducted into the Acad- do not shy away from their vicious the memoir. He concludes with his emy in 1925. Her memoir is a fascinat- competition. own insights and observations from ing one and well worth reading. continued on page 12
The Nucleus December 2013 7 Summer Scholar Report Asymmetric Mannich Reactions via Pseudoephenamine Glycinamide Enolization Claire S. Harmange*, Ian B. Seiple, Robin J. Sussman, Andrew G. Myers Department of Chemistry and Chemical Biology, Harvard University Since the discovery of penicillin G (1, Fig. 1) nearly 75 years ago, β-lactams are some of the most widely prescribed antibiotics in the United States and around the world. Rap- idly increasing resistance to β-lactams is threatening the limited arsenal of antibiotics available to physicians, and the lack of innovation and momentum in the field of antibiotic development has caused the drug pipeline to virtually dry out. Significant research in the practical and variable synthe- sis of antibiotics playing a central role in the battle against resistant bacteria.1a,b The β-lactam’s characteristic four-membered ring exerts its antibacterial effect by interfering with bacterial cell wall synthesis. In binding to the bacteria’s β-lactam- binding enzymes called PBPs (penicillin-binding proteins), the drug inhibits cell wall synthesis, eventually leading to cell death. Resistance mechanisms include: changes in one or more of the PBPs, which decreases the drug’s ability to bind to the target bacteria; changes in cell wall porins, which The Myers group has shown that stereocontrolled syn- prevent penetration of the antibiotic;i and finally, bacterial thesis of syn-β-hydroxy-α-amino acids can be achieved via xi production of β-lactamases, which deactivates the antibiotic direct aldolization of pseudoephenamine glycinamide. before it can reach its target.ii Analoguous enolization of pseudoephenamine glycinamide The discovery of nocardicins (2, Fig. 1) in 1976, as well (4) followed by the trapping an imine electrophile was as others, prompted new interest in the pharmaceutical expected to deliver a diastereoselective Mannich reaction potential of monocyclic β-lactams, which has motivated and produce the desired diamine (5) β-lactam precursor chemists to develop a variety of routes to these compounds.ii (Fig. 2). Most notable among these is Aztreonam (3, Fig. 1), which Initial challenges in the project involved the choice of represents the only fully synthetic monobactam to be devel- electrophile. Trimethylsilyl-benzaldimine was at first oped as a commercial drug in the United States.i Develop- selected for its lability and consequent potential for simulta- ments in the synthesis of monocyclic β-lactams have neous cyclization the β-lactam and cleavage of the auxiliary included cyclization of amino acids,v [2+2] cycloaddition of upon formation of the Mannich adduct. Several attempts to ketenes and imines,v ester enolate-imine condensations,vi effect a Mannich coupling with TMS-imine were unsuccess- and others.vi Asymmetric enolate-imine condensations have ful, leading instead to the transimination product (6, Scheme been reported using (S,S)-pseudoephedrinei and chiral oxa- 1). By switching to Boc-imines, successful Mannich cou- zolidinones;x however, these syntheses lack amino function- pling was achieved. Boc-p-toluelbenzaldimine yielded a ality at the C-3 position important to monocylic β-lactams 95% yield of major diastereomer showing promise for a activity. Using chemistry developed by the Myers group highly diastereoselective reaction (6, Scheme 2). Absolute with pseudoephenamine glycinamide, this project aims to determination of the product’s stereochemistry remains to be synthesize αβ-diamino acids, which are precursors to mono- determined via X-ray crystollography. The success of the cyclic β-lactam candidates. Boc-imine electrophile indicates potential for the synthesis
8 The Nucleus December 2013 of a variety of other Mannich adducts from a variety of Boc- imines. To date, Boc-p-bromobenzaldiminexii has also been Sukant Tripathy successfully used as a Mannich substrate (8, Scheme 2). Completing the β-lactam synthesis required removal of Annual Memorial Symposium Friday, December 6, 2013 8 a.m. to 4:30 p.m. UMass Lowell Inn and Conference Center, 55 Warren St., Lowell, MA 01854 Directions can be found in the ICC’s website: http://www.acc-umlinnandconferencecenter.com/maps- directions. The program includes talks by invited speakers and poster presentations. Speakers: E. Bryan Coughlin, University of MA Amherst Alan Dalton, University of Surrey, U.K. Jeremiah Johnson, MIT Changshu Kuo, National Cheng Kung University, Taiwan Ramanathan Nagarajan, U.S. Army NSRDEC Prakash Rai, University of MA Lowell TBA the auxiliary and deprotection of the Boc group to yield the Registration: Pre-Registration (FREE) is required by November 29, 2013 to [email protected] or 978- corresponding alpha,β-diamino acid. Auxiliary cleavage in basic conditions gave the water-soluble carboxylate diamine 934-3695. Lunch and refreshments will be provided (so (9, Scheme 3). Boc deprotection in TFA proceeded cleanly accurate count is required). Please request vegetarian lunch- (10); however, subsequent cyclization attempts using eon if preferred. u Mukaiyama’s reagent have yielded inconsistent results. Dif- ficulty purifying the water-soluble cyclization substrate as well as the water sensitive nature of the cyclization may Chemical Synthesis of Antibiotics (Eds.: G. Lukacs, explain the unsuccessful results. Recent success in cleavage M. Ohno), 1990, pp. 534-564. of the Boc group with the substrate still attached to the aux- iv R. B. Sykes, D. P. Bonner, Reviews of Infectious Dis- iliary offers the possibility of a cleaner cyclization route. eases, 1985, 7, S579-S593. Continued work on this project will involve further explo- v M. J. Miller, P. G. Mattingly, M. A. Morrison, J. F. ration of cleavage methods and cyclization pathways as well Kerwin, Jr, J. Am. Chem Soc. 1980, 102, 7026. as diversification of possible Mannich adducts with a vari- vi ety of imine electrophiles. C. Hubschwerlen, G. Schmid , Helv. Chim. Acta., 1983, 66, 2206. References vii David J. Hart, Deok-Chan Ha, Chem. Rev. 1989, 1a The Antibiotic Alarm. Nature. 2013, 495, 141. 89, 1447-1465. 1b L.L. Silver, Clinical Microbiology Review. 2011, viii Thomas C. Richard, in Recent Progress in the 24, 71-109. Chemical Synthesis of Antibiotics (Eds.: G. Lukacs, i J. Pitout, C. Sanders, E. Sander, J. Am. Med. 1997, M. Ohno), 1990, pp. 534-564. 103, 51-59. ix A. Iza, J. Vicario, L. Carrillo, D. Badia, Synthesis, ii W. Durkheimer, J. Blumbach, R. Lattrell, K. Sche- 2006, 23, 4065-4074. unemann, Angew. Chem. Int. Ed. Engl. 1985, 24, x I. Abrahams, M. Motevalli, , A. Robinson, P. Wyatt, 180-202. Tetrahedron, 1994, 50, 12755-12772. iii Thomas C. Richard, in Recent Progress in the xi I. B. Seiple, J. A. M. Mercer, R. J. Sussman, A. G. Manuscript in preperation. [*] C. S. H acknowledges the ACS for its financial support xii A. G. Wenzel, E. N. Jacobsen, J. Am. Chem. Soc. through the NESACS Norris-Richards Research Scholar- u ship. 2002, 124, 12964-12965.
The Nucleus December 2013 9 Photos from the German Exchange at NERM Photos by Morton Z. Hoffman
Marinda Wu chatting with members of the German delegation Members of the German delegation and NESACS German Exchange Steering Com- after the symposium: (l-r) Jens Breffke, Wilma Neumann, Torsten mittee with Marinda Wu (ACS President), at center, after the symposium: (l-r) Denise John, Susanne Leubner, Tanja Scholz, Martin Lichtenthaler, Schütz, Wilma Neumann, Torsten John, Jackie O'Neil, Mike Strem, Ruth Tanner, Jens Andreas Seitz, Elisabeth Kapatsina. In background: Mike Neu- Breffke, Heidi Teng, Morton Hoffman, Anna Hofmann, Peter Sponholz, Martin Licht- mann, Christian Weinberger. enthaler, Mike Neumann, Christian Weinberger, Susanne Leubner, Stefan Zajonc, Tanja Scholz, Andreas Seitz, Elisabeth Kapatsina, Alfred Flint.
(l-r) Morton Hoffman (Boston University), Elis- abeth Kapatsina (German Chemical Society), Mike Strem (Strem Chemicals). Members of the German delegation and the NESACS Steering Committee with friends at the NERM dinner. (l-r) Seated: Rajeev Chorghade, Jackie O'Neil, Martin Lichtenthaler, Elisabeth Kapatsina, Andreas Seitz, Keeve Gurkin; standing: Peter Sponholz, Alfred Flint, Tanja Scholz, Jens Breffke, Susanne Leubner, Stefan Zajonc, Anna Hofmann, Denise Schütz, Heidi Teng, Mike Neumann, Christian Weinberger, Wilma Neumann, Torsten John.
Have you seen it on the NESACS website? Updated frequently • Late-breaking news • Position Postings Back issues of the Nucleus • Career-related Links • Awards and Scholarship Mike Strem (Strem Chemicals) at left with Alfred Flint (University of Rostock) at the Strem Chem- WWW.NESACS.org icals exhibitor booth.
10 The Nucleus December 2013 German Exchange NESACS Continued from page 10 Archives Have Moved The NESACS Archives were moved from their location of many years in the basement of the Regis College Library to a new temporary location at Sigma-Aldrich Corporation in Natick, MA. A more permanent long-term storage location is desired. Denise Schütz (University of Frankfurt), "Con- Mike Neumann and Wilma Neumann discuss NESACS expresses great appreci- formational Flexibility of Toc34 Homodimer Anna Hofmann's poster with her. ation to Regis College for allowing Studied by PELDOR." NESACS to store its archives in its library. NESACS is further apprecia- tive of Michael Singer and Sigma- Aldrich for making storage space available while a more permanent solution is sought. u
Q. Exactly, how many awards and scholarships does NESACS sponsor? A) One b) Two c) Many www.nesacs.org/awards (l-r) Seated: Anna Hofmann, Jackie O'Neil, Mike Strem (Strem Chemicals) at left with Jens Wilma Neumann; standing: Peter Sponholz, Breffke (Pennsylvania State University). Andreas Seitz
(l-r) Susanne Leubner, Heidi Teng, Tanja Scholz
What’s Yours? Many local employers post positions on the NESACS job board. Find yours at www.nesacs.org/jobs
The Nucleus December 2013 11 Biographical Memoirs NESACS SE-MA Event NERACS Report Continued from page 7 Continued from page 4 Continued from page 2 I was disappointed that Stephen inger of that institution as the General Jay Gould’s memoir has not been writ- Chair. The Binghamton Section is ten. His book “Wonderful Life” about expected to submit a bid to host all the strange and wonderful fossilized NERM 2016 to celebrate its 75th creatures discovered in the Burgess anniversary. The Central New York Shale is one of my favorites. and Rochester Sections have made The nuclear physicists involved separate expressions of interest for with the creation of the atomic bomb NERM 2017. NERM 2018 is currently are well represented in the memoirs. open; the Rhode Island Section will Most recently the Philip Morrison and explore the option for an October Edward Teller memoirs were published meeting that year in Providence or to join that of J. Robert Oppenheimer. Provost Karim Newport, perhaps in connection with Albert Einstein is there along with transforming power of chemistry”) and the Southeastern Massachusetts area of Thomas Edison. It is interesting to note mission (“Advance the broader chem- NESACS. that Edison was not inducted until istry enterprise and its practitioners for The next meeting of the NERACS 1927 when he was 80 years old. I the benefit of Earth and its people”) of Board will be at a 2014 National ACS guess having a record number of US the ACS, the structure of the Society meeting, probably in San Francisco in Patents was not sufficient for member- (local sections, technical divisions, August. u ship to the Academy until the sheer committees, publications, staff, and volume and economic impact over- volunteers), and its core values (pas- Abstract whelmed the selectors. Notably, his sion for chemistry in the broadest memoir was published in 1932 only a sense, focus on members, professional- Continued from page 5 year after his death. ism, diversity and inclusion). She then and development of a novel, potent, There is an iPad application that explored in detail the current strategic selective, and orally and CNS-penetra- makes accessing the memoirs very plan: ble H3R antagonist/ inverse agonist for simple. You will immediately see a tab • Provide information: Be the most treatment of cognitive impairment listing of eighteen of the most recently authoritative, comprehensive, and associated with AD and Schizophrenia. published memoirs. This tab is fol- indispensable provider of chemistry- This presentation will describe our lowed by a “featured” tab which is cur- related information; medicinal chemistry efforts towards this goal, beginning with biological rently honoring NAS Nobel Laureates • Advance members careers: Empower concept through HTS and finally DC such as Hans Bethe, Bruce Merrifield, an inclusive community of members, selection. u and Theodore William Richards. with networks, opportunities, I highly recommend these mem- resources and skills to thrive in the oirs as an informative and inspirational global economy; pated in the inauguration of the new window into the lives of these great 400-MHz NMR facility. scientists. The NAS membership • Improve education: Foster the devel- opment of the most innovative, rele- Plans are now being developed for includes a rich selection of the most further events in SE-MA and an inau- influential scientists of the last 150 vant, and effective chemistry education in the world; gural one in NH during 2014. Modest years. These biographical memoirs are funds to support the program into the • Communicate chemistry’s value: a treasure. u next year were received by NESACS Communicate chemistry’s vital role as an innovative project grant from the in addressing the world’s challenges ACS Local Sections Activities Com- THE COMMITTEE ON to the public and policymakers. mittee (LSAC). A survey of the atten- CHEMICAL ABSTRACTS After a question and answer period, the dees at the October 3rd event indicated (CCAS) WANTS YOUR attendees mingled and spoke with Ms. a strong interest in future activities in FEEDBACK Jacobs while enjoying a reception of SE-MA and a willingness of many to heavy hors d’oeuvres provided by become actively involved. u Visit our page on ACS Network: Jeannette Riley, Dean of the UMD https://communities.acs.org/groups/ College of Arts and Sciences. Join NESACS chemical-abstracts-service-committee Earlier in the day, Ms. Jacobs met with members of the faculty and stu- or contact Michael Filosa with dents in the Department of Chemistry on facebook any suggestions at [email protected] and Biochemistry, toured the research www.facebook.com/nesacs and teaching laboratories, and partici-
12 The Nucleus December 2013 NERM 2013 Report Photos from the Northeast Continued from page 6 • Hydrogen production and storage for a sustainable energy economy Regional Meeting (organometallic chemistry and cataly- October 23-26, 2013, New Haven, Connecticut sis) – Peter Sponholz Photos by Morton Z. Hoffman • Research-experiencing learning in the student-based project “Make Sci- ence!” (chemical education) – Stefan Zajonc • Applied gallium(I) chemistry: Syn- thesis of highly reactive polyisobuty- lene (organometallic chemistry and catalysis) – Martin Lichtenthaler • COX inhibitors with caraboranes as pharmacophore (medicinal chem- istry) – Wilma Neumann • Synthesis, structure, and magnetic properties of tin-substituted iron Donna Nelson (University of Oklahoma), scien- (l-r) Sandy Hoffman, Marinda Wu (ACS Presi- nitrides Sn Fe N (poster) – Tanja tific advisor for Breaking Bad, at left with Ruth dent), Doris Lewis (Suffolk University), Kath- x 4-x Tanner (University of Massachusetts Lowell), leen Schulz (ACS Director-at-Large), Julie Scholz NESACS Immediate Past Chair. Smist (NERACS Chair), Dorothy Phillips • Novel phosphorous-carbon cages (NESACS Councilor). (poster) – Andreas Seitz • Synthesis and evaluation of mannose derivatives as Pseudomonas aerugi- nosa lectin LacB antagonists (poster) – Anna Hofmann • Influence of the surface ligand den- sity on the optical properties of semi- conductor nanocrystals (nanoscience) – Susanne Leubner • Conformational flexibility of Toc34 Homodimer studied by PELDOR (poster) – Denise Schütz Mukund Chorghade (Thinq Pharma) with his Ken White (NERM General Co-Chair) at left Accommodations at the Omni Hotel wife, Veena, and son Rajeev (Carnegie Mellon receiving a plaque of recognition from Tom and registration at NERM, which University). Gilbert (ACS District I Director). included participation in the welcome reception, social mixer, keynote dinner High School, who received the 2013 Committee on Chemistry and Public with Donna Nelson (University of ACS Division of Chemical Education Affairs and the Committee on Public Oklahoma), and awards dinner with Northeast Region Award for Excel- Relations and Communications. Marinda Wu, were provided for the lence in High School Teaching. There will be no Northeast German delegation by NESACS. A Closer to home, also honored at Regional Meeting in 2014. The next global innovation grant of $4,000 from the awards dinner was Doris Lewis NERM will be held in Ithaca, NY, on the ACS International Activities Com- (Suffolk University), who received the June 10-13, 2015, on the campus of mittee partially covered those 2013 E. Ann Nalley Northeast Region Ithaca College; Akiko Fillinger of that expenses. Award for Volunteer Service to the institution will serve as the General Attendees at the keynote dinner ACS for her activities with the multi- Chair. The plenary speaker will be had the opportunity to hear Prof. Nel- award-winning student chapter at her Esther Takeuchi (SUNY Stony Brook), son describe her activities as scientific institution, with NESACS as section who received the 2013 E.V. Murphree advisor to the popular television pro- chair, leader in the creation of Connec- Award in Industrial and Engineering gram, Breaking Bad, and to meet her tions to Chemistry and the Phyllis A. Chemistry from the ACS for her inno- personally. Honored at the awards din- Brauner Memorial Lectures, and chair vative work on advanced battery ner was Sharon Palmer, a chemistry of the Government Affairs Committee, power sources. u teacher at Amherst (MA) Regional and at the national level with the ACS
The Nucleus December 2013 13 BUSINESS DIRECTORY
SERVICES SERVICES SERVICES
14 The Nucleus December 2013 BUSINESS DIRECTORY
SERVICES SERVICES CAREER SERVICES
Index of Advertisers Eastern Scientific Co...... 11 Mass-Vac, Inc...... 4 Micron, Inc...... 14 NuMega Resonance Labs14 Organix, Inc...... 14 PCI Synthesis...... 14 Rilas Technologies, Inc. ..15 Robertson Microlit Labs..14 Tyger Scientific, Inc...... 14 Tyger Scientific ...... 14 VACUUBRAND ...... 15 Waters Corporation...... 15
The Nucleus December 2013 15 Harvard, MA 01451 19 Mill Road A Plea for Local Section Dues When you receive your dues bill from National ACS it will include an item for Northeastern LS Voluntary Dues of $22. Every member of ACS who lives in New Hampshire or eastern Massa- chusetts is automatically a member of the Northeastern Section (NESACS). These dues are voluntary, and about half of our 6500 members choose not U.S. POSTAGE PAID NONPROFIT ORG. NORTHEASTERN to pay them. As Treasurer of NESACS, I would like to urge all members to pay these dues and support the Section activities, even if you do not regularly attend NESACS meetings. Dues constitute the major source of discretionary Dec 04 income to the Section. While most awards programs are supported by Calendar Prof. Joel Rosenthal (U. of Delaware) UMass Dartmouth, Dion Building-Rm 115 Trust funds, your dues and contribu- Check the NESACS home page 4:00 pm tions fund activities such as those of for late Calendar additions: Dec 05 the Education Committee, National Chemistry Week, Younger Chemists, http://www.NESACS.org Prof. Sanjay Mathur, (U. of Cologne) Boston College, Merkert 130 4:00 pm and Project SEED, all of which benefit Note also the Chemistry Department web the general chemical community. pages for travel directions and updates. Dec 06 Non-payment of Local Section These include: Sukant Tripathy Memorial Symposium 2013 http://www.bc.edu/schools/cas/chemistry/semina UMass Lowell Inn and Conference Center dues has no effect on the individual rs.html 55 Warren St., Lowell, MA 01854 member. ACS does not permit us to http://www.bu.edu/chemistry/seminars/ 8 am to 4:30 pm http://www.brandeis.edu/departments/chemistry/ discriminate between members who events/index.html Pre-registration is required. Contact: pay dues and those who do not, so, for http://www.chem.harvard.edu/courses/seminars. [email protected] 978-934-3695 example, the Nucleus is sent to all php members by mail or electronically. http://chemcalendar.mit.edu/index.php Dec 09 http://chem.tufts.edu/seminars.html Members for whom dues are non- Prof. Joseph Sadighi, (Georgia Tech) http://engineering.tufts.edu/chbe/newsEvents/se deductible might prefer to send a con- “Small Clusters of Group 11 Metals Supported minarSeries/index.asp tribution to NESACS, since http://www.chem.umb.edu By N-Heterocyclic Carbenes” http://www.umassd.edu/cas/chemistry/ Brandeis, Gerstenzang 121 contributions to the Section are tax http://www.uml.edu/Sciences/chemistry/Seminar 4:00 pm deductible. Checks payable to s-and-Colloquia.aspx Prof. Eun Suk Kim (Brown University) NESACS can be sent to the Treasurer http://www.unh.edu/chemistry/events Boston University, Metcalf Rm 113 4:00 pm at 19 Mill Rd., Harvard, MA 01451 or Dec 02 Dec 11 to the administrative secretary. Prof. Jeffrey Long (U.C. Berkeley) Physical Chemistry Seminar Your support of the Section is Harvard University, Pfizer Hall Prof. John Tully (Yale University) greatly appreciated, and the Board of 4:15 pm MIT, Rm 4-231 Directors conscientiously strives to see Dec 03 4:00 pm that all Section activities advance the Prof. Bing Xu (Brandeis University) Dec 18 chemical enterprise. “Exploring Molecular Nanomaterials in Cellular Physical Chemistry Seminar Environments” Prof. Adam Willard (MIT) -Jim Piper, NESACS Treasurer u Tufts U., Pearson P-106, 4:30 pm Boston University, Metcalf Rm SCI512 Prof/ Yan Jessie Zhangm (U. of Texas-Austin) 2:00 pm Boston College, Merkert 130 4:00 pm Notices for The Nucleus Calendar of Seminars Prof. Jonathan Rochford (UMass-Boston) Your one-stop source to career-related U. New Hampshire, Room N104 (L103) should be sent to: links in the Chemical Sciences 11:10 am Michael Filosa, email: Michael.filosa(at)verizon.net u WWW.NESACS.ORG/CAREERS