Gustafson Group @ Stony Brook

Asymmetric Synthesis and Chemical Biology

[Gustafson Group @ Stony Brook @GustafsonLab]

We hope people find this useful, and it helps stimulate discussion and thought on how best to set atropisomeric axes in practical settings.

[Gustafson Group @ Stony Brook @GustafsonLab]

We did a thing! https://t.co/U9H9LH2Pmb
This review, which is part of a themed collection on axially chirality, was written with the goal of sharing some fundamentals and capturing a 'snapshot' of the state of atropisomerism in drug discovery.

[Gustafson Group @ Stony Brook @GustafsonLab]

One thing worth mentioning is the majority of examples utilized tried and true chiral resolution chemistry, however there was a lot of innovation in recycling of the unwanted atropisomer. There were also a few examples of asymmetric catalysis being employed.

[Gustafson Group @ Stony Brook @GustafsonLab]

Excited to announce that the preliminary program for the 2027 Gordon Research Conference on Heterocyclic Compounds, June 20–25 in Newport, RI, is online!
https://t.co/NnW86efApu
We have an outstanding lineup of academic and industry scientists. Hope to see many of you there!

[Gustafson Group @ Stony Brook @GustafsonLab]

@djavko Great news, Zarko! Welcome to the area.

[Gustafson Group @ Stony Brook @GustafsonLab]

You forgot to mention the PhD's beat the PhD Candidates in volleyball

[Lipshultz Group @LipshultzSBU]

a successful beach day (most) of the organic chemistry groups along with a PhDs vs Candidates volleyball match! (a few injuries, no deaths) @GustafsonLab @jillalty @barneygrubbs @QJBruch Prof. Katherine Aubrecht and Prof. Matthew Parkers Group

[Gustafson Group @ Stony Brook @GustafsonLab]

The S-Atropisomer* had no KIT activity, but displayed intriguing selectivity towards LYN kinase, an emerging target for the treatment of cancer, autoimmune diseases and inflammatory conditions, that currently lacks highly selective inhibitors.

[Gustafson Group @ Stony Brook @GustafsonLab]

Another day another preprint on ChemRxiv!
“Leveraging Atropisomerism to Obtain a Mutant-Selective c-KIT Inhibitor in Gastrointestinal Stromal Tumors”
A story of privileged heterocycles, atropisomerism and kinase selectivity.
https://t.co/tlSyYPLCQT

[Gustafson Group @ Stony Brook @GustafsonLab]

The R-atropisomer* maintained potency against cellular models of GIST (IC50 < 10 nM) while displaying improved target selectivity, including towards key oncogenic c-KIT mutants. *Cahn-Ingold-Prelog priorities cause the analogs to have opposite stereochemical descriptors.*

[Gustafson Group @ Stony Brook @GustafsonLab]

This led us to introduce a peri Fluoro group as a H-bonding handle to ‘lock’ that axis into the trans conformation. This seemingly simple modification led to a dramatic increase in HER selectivity, particularly towards HER4, a kinase with emerging implications in ovarian cancer.

[Gustafson Group @ Stony Brook @GustafsonLab]

Excited to share our new ChemRxiv preprint:
“Leveraging Conformational Control of Neratinib’s C–N Axes to Enhance HER4 Selectivity in Ovarian Cancer”
congrats to the tam @StonyBrookChem and @SDSUChemBiochem
Read here: https://t.co/0gyoBcOgUc

[Gustafson Group @ Stony Brook @GustafsonLab]

The ‘conformational mapping’ of diarylamine crystal structures suggested that the pan-HER kinase inhibitor neratinib adopts two planar conformations around a C–N axes (similar to cis and trans alkenes). HER family kinases generally preferred the ‘trans’ conformation

[Gustafson Group @ Stony Brook @GustafsonLab]

The final version of this manuscript is up at @ACSCatalysis
https://t.co/RGUESD8DI9

[Gustafson Group @ Stony Brook @GustafsonLab]

I am sharing this preprint from my group. Inspired by all the great recent skeletal editing work, we developed an atropisomer selective strategy to take Indoles to quinolines. https://t.co/0QbvvTBSmn...

[Jeff Lipshultz @jeflip]

Our department (@StonyBrookChem) is looking for a PRODiG+ fellow – the appointment is two years, followed by conversion to a tenure-track assistant professor at the conclusion of the fellowship. A unique opportunity!
https://t.co/eQwXVBmTdc

[Gustafson Group @ Stony Brook @GustafsonLab]

Reposting. One more week until the deadline!

[Gustafson Group @ Stony Brook @GustafsonLab]

The Stony Brook Chemistry Department is searching for a Chemical Biologist at the Associate or Full professor Level. Come join us on Long Island and do some great science! https://t.co/rdDzReWL0s

[NaOH Bartfield, PhD 🧪 @NaOHBartfield]

Doctor Gavin Rustin we salute you

[Gustafson Group @ Stony Brook @GustafsonLab]

Check out our latests work in collaboration with @Taylorlab_Chem ! We evaluated their biomolecular photocaged trifluormethylation reagent on small molecules, finding it effected the rapid trifluoromethylation of diverse aromatics, including several APIs.
https://t.co/lS1020lIrA

[Gustafson Group @ Stony Brook @GustafsonLab]

The Stony Brook Chemistry Department is searching for a Chemical Biologist at the Associate or Full professor Level. Come join us on Long Island and do some great science! https://t.co/rdDzReWL0s