Four Brandeis Science Grads Receive 2016 NSF Graduate Fellowships

GRFP_logoA science education at Brandeis University can be a springboard to future science achievements. We would like to congratulate four of our science graduates who have received the prestigious National Science Foundation Graduate Research Fellowships for 2016.

Noam Saper

Noam was an outstanding student graduating summa cum laude with highest honors in Chemistry in 2015. At Brandeis, Noam worked in the labs of Prof. Barry Snider and Prof. Christine Thomas. He co-authored 3 publications with Snider and Thomas.

Noam received multiple awards including the Barry M. Goldwater Scholarship (2014); the Elihu A. Silver Prize (2014); and the Doris Brewer Cohen Endowment Award (2015).

Following graduation and enthralled by the mysteries of the west coast, he decided to attend the University of California, Berkeley. Noam is working on mechanistic studies of Ni-catalyzed diaryl ether hydrogenolysis in Professor John Hartwig’s laboratory.

Alexandra Sun

Another outstanding Chemistry student, Alexandra Sun graduated magna cum laude with highest honors in 2015. Alexandra also worked in Christine Thomas’ lab where she carried out research on Transition Metal Complexes Featuring a Redox-Active Bidentate Amido-Phosphido Ligand. Alexandra received the Melvin M. Snider Prize in Chemistry in 2015.

She is currently a first-year student in the Chemistry Department at the University of Michigan working with Professor Corey Stephenson on developing new methods in photoredox catalysis.

Abigail Zadina

Abigail received her BS/MS in Neuroscience in 2013. Working in Michael Rosbash’s lab, she was a co-author on 2 publications and received numerous awards including the Doris Brewer Cohen award and the Elihu Silver Prize. In 2013, Abigail discussed her science experience in the Brandeis publication Imprint.

Following graduation, Abigail worked at Columbia in Richard Axel’s lab. She is currently a PhD student in Neurobiology and Behavior at Columbia University.

Joseph Jacobowitz

Joseph Jacobowitz received his BS/MS in 2014, graduating summa cum laude with Highest Honors in Biochemistry. While a Brandeis undergraduate, Joseph co-authored a publication with his faculty mentor, Doug Theobald. In 2013, Joseph received the Division of Science Prize for Outstanding Research Accomplishment and the William P. Jencks  Award in Biochemistry in 2014.

Joseph is in the Biology PhD program at MIT, working for Jing-Ke Weng on the origins of chemodiversity in plants.

Summer Research at Brandeis

All four science graduates had the opportunity to jump start their careers by doing summer research at Brandeis. Noam, Alexandra and Joseph were Division of Science Summer Undergraduate Research Fellows (SURF). Abigail received a Computational Neuroscience Traineeship.

These undergraduate research programs enable students to spend their summers at Brandeis engaged in intensive undergraduate training and summer research. Both programs provide a stipend, faculty mentoring and full-time lab research. The Summer Undergraduate Research Fellows work culminates in a poster presentation summarizing their work. The SURF program is funded by generous donations from alumni. The Computational Neuroscience Traineeship program begins in the summer and runs through the following academic year. It is funded through a grant from the National Institute on Drug Abuse. 

Noam Saper ’15 named Goldwater Scholar

Noam Saper ’15, a Brandeis Chemistry major, has been named a Goldwater Scholar by The Barry Goldwater Scholarship and Excellence in Education Program. An exceptional student, Noam has been doing research with Christine Thomas and also with Barry Snider, seeking out experience in both organic and inorganic synthetic chemistry, with publication in press already from each lab.  Noam was a 2013 recipient of a Division of Science Summer Research Fellowship and a Teaching Assistant for Organic Chemistry Lab. He is also a Lerman-Neubauer Fellow, an Undergraduate Departmental Representative for Chemistry, and an active member in the Brandeis Orthodox Organization, In short, Noam is a hard-working and engaged member of the Brandeis community, and very deserving of this distinctive honor.


Noam presenting at a recent ACS national meeting

The Scholarship Program honoring Senator Barry Goldwater was designed to foster and encourage outstanding students to pursue careers in the fields of mathematics, the natural sciences, and engineering. The Goldwater Scholarship is the premier undergraduate award of its type in these fields. Goldwater Scholars have very impressive academic qualifications that have garnered the attention of prestigious post-graduate fellowship programs. Recent Goldwater Scholars have been awarded 80 Rhodes Scholarships, 117 Marshall Awards, 112 Churchill Scholarships, and numerous other distinguished fellowships such as the National Science Foundation Graduate Fellowships.

Snider named ACS Fellow

Charles A. Breskin Professor of Organic Chemistry Barry Snider has been named a Fellow by the American Chemical Society (ACS). ACS members are selected as fellows to recognize and honor their outstanding achievements in and contributions to science, the profession, and ACS. Fellows will be inducted at the ACS National Meeting in Denver on Aug. 29. Snider’s work in recent years has focused on total synthesis of natural products, a dazzling array of which are shown on his website: Recent stories on this blog discussing new syntheses from the Snider lab include:



Biomimetic Route to Maldoxin

In their recent Organic Letters paper entitled the Syntheses of Chloroisosulochrin and Isosulochrin and Biomimetic Elaboration to Maldoxin, Maldoxone, Dihydromaldoxin, and Dechlorodihydromaldoxin, the Snider lab at Brandeis developed an efficient biomimetic synthesis of maldoxin (4), the biological precursor of several cytotoxic natural products recently isolated from the plant endophytic fungus Pestalotiopsis fici. Chloroisosulochrin (1) was synthesized for the first time and elaborated to maldoxin (4) by a three-step biomimetic route consisting of oxidative cyclization to give spirofuranone 2, acid catalyzed ring opening to yield dihydromaldoxin (3) and a second oxidative cyclization to form maldoxin (4).

Electrophilic chlorination of phenols usually takes place unselectively at both ortho and para positions.  For the synthesis of chloroisosulochrin, they developed an ortho selective chlorination using 2,2,6,6-tetramethylpiperidine and sulfuryl chloride.  Presumably a hindered N-chloroamine is formed, which hydrogen bonds to the phenol and delivers electrophilic chlorine intramolecularly.

New route to lycopodium alkaloids

The lycopodium alkaloids are a large and extensively studied alkaloid family. Huperzine A (1), the medicinally most significant lycopodine alkaloid as a potential treatment for Alzheimer’s disease, functions as an acetylcholinesterase inhibitor but may have other roles as has been addressed in several recent reviews.  Sauroine (2, 7,8-dihydroxylycopodine), from Huperzia saururus, was reported in 2004 and shown in 2009 to improve memory retention in the step-down test in male Wistar rats, significantly increasing hippocampal plasticity. 7-Hydroxylycopodine (3), from Huperzia serrata, was also reported in 2004 and may have related biological activity.

In their recent Organic Letters paper entitled the Synthesis of (±)-7-Hydroxylycopodine, the Snider lab at Brandeis developed a new general route to these bridgehead hydroxylated lycopodines. They reported a practical six-step synthesis of 7-hydroxylycopodine which makes it readily available for further biological evaluation. The key step of the synthesis is the treatment of bicyclic enol ether 4 with 60% sulfuric acid that affords tricyclic amino alcohol 5, which is further elaborated to 7-hydroxylycopodine (3) in three steps. The application of this route to the synthesis of sauroine (2) is now under investigation.

Phantasmidine, a Nicotinic Receptor Agonist from Ecuadoran Poison Frogs

IIn 1992, the lab of the late John Daly at NIH reported the isolation of epibatidine (1) from the skin of an Ecuadorian poison frog.  In addition to being a toxin, epibatidine has potent analgesic activity. Subsequent studies showed that this activity resulted from interaction with acetylcholine nicotinic receptors (nAChRs) with binding to some of the receptors at sub nanomolar levels.  The binding to several different types of nAChRs may be responsible for its non-selective activity.

In 2010, the Daly group reported the isolation and tentative structure determination of the epibatidine congener phantasmidine (2) from a total sample of only 20 micrograms. Preliminary biological studies with the limited material available indicated that phantasmidine (2) differs from epibatidine (1) by being selective for β4-containing nicotinic receptors, suggesting that phantasmidine might fill a niche for characterization of these receptors. However, the limited natural material available precluded detailed pharmacological analysis and definitive structure determination.

In their recent paper in Organic Letters entitled the Synthesis of Phantasmidine, the Snider lab at Brandeis reported a short and efficient synthesis of phantasmidine that confirmed the tentative structure and makes ample material readily available for further biological evaluation, which is currently in progress.  To prepare the tetracyclic framework, they invented a new tandem intramolecular aldol reaction-nucleophilic aromatic substitution reaction to form both five membered rings in a single reaction.   Treatment of keto amide 3 with sodium hydroxide gave aldol adduct 4 which cyclized to lactam 5.  Reduction of the lactam completed a practical synthesis of phantasmidine (2).

Protected by Akismet
Blog with WordPress

Welcome Guest | Login (Brandeis Members Only)