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NOBEL PRIZE
CLICK AND BIOORTHOGONAL CHEMISTRY WIN 2022 NOBEL PRIZE IN CHEMISTRY
CAROLYN R. BERTOZZI, MORTEN MELDAL, AND K. BARRY SHARPLESS RECEIVE PRIZE FOR
THEIR WORK ON REACTIONS THAT QUICKLY LINK MOLECULES AND THE APPLICATION OF THE
REACTIONS IN LIVING CELLS
BY MARK PEPLOW, SPECIAL TO C&EN
OCTOBER 5, 2022 | A VERSION OF THIS STORY APPEARED IN VOLUME 100, ISSUE 36
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* Click and bioorthogonal chemistry win 2022 Nobel Prize in Chemistry
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* Carolyn Bertozzi’s glycorevolution
Credit: Laura Morton (Bertozzi), University of Copenhagen (Meldal), Sandy
Huffaker (Sharpless)
From left: Carolyn R. Bertozzi, Morten Meldal, and K. Barry Sharpless
MORE ONLINE
Listen to a special episode of C&EN’s podcast, Stereo Chemistry, about the
prize: cenm.ag/nobelpod22.
Three scientists have won the 2022 Nobel Prize in Chemistry: Carolyn R. Bertozzi
of Stanford University, Morten Meldal of the University of Copenhagen, and K.
Barry Sharpless of Scripps Research in California share the prize for their work
on click chemistry and bioorthogonal reactions. Click chemistry involves
reactions that unite two synthetic molecules quickly and irreversibly. Some of
these reactions can be performed inside living cells without disrupting
biochemical processes, making them bioorthogonal.
This approach is used to tag biomolecules with fluorescent probes that
illuminate the inner workings of cellular biochemistry, for example, and it also
offers a way to produce antibody-drug conjugates that have highly targeted
therapeutic action in the body. Click chemistry is even being directly applied
inside patients, in ongoing clinical trials of a powerful cancer therapy. “I
truly believe that the potential applications of click chemistry are
unlimited—from materials science to life-saving drugs, click chemistry is here
to stay,” said John Moses, a click chemistry researcher at Cold Spring Harbor
Laboratory, in an email to C&EN.
Related: C&EN Trailblazers - One on one with Carolyn Bertozzi
“It has led to a revolution in how chemists think about linking molecules
together,” said Johan Åqvist, chair of the Nobel Committee for Chemistry, during
the Stockholm press conference to announce the award. The scientists will each
share one-third of the 10 million Swedish kronor (approximately $900,000) prize.
“I can hardly breathe,” Bertozzi said during the press conference. “I’m still
not entirely positive that it’s real, but it’s getting realer by the minute.”
Credit: Biomacromolecules
A glycan modified with an azide group expressed on the surface of a cell acts as
a handle for attaching functional molecules. Researchers attached a polymer
containing a fluorescent group (green) to the cell via a click reaction.
“We are absolutely delighted with these awards, which recognize the enormous
impact of click chemistry and bioorthogonal chemistry,” American Chemical
Society president Angela K. Wilson said in a press statement. ACS publishes
C&EN.
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Sharpless and Meldal independently developed the first click reaction about 20
years ago. The copper-catalyzed reaction between an azide and an alkyne produces
a highly stable triazole as the single product. “It's still the crown jewel of
click reactions,” said Nobel committee member Olof Ramström at the press
conference.
Chemists had long used this kind of cycloaddition reaction, but the copper
catalyst was the key to making it rapid and selective. “You can take molecules
that are highly functionalized and click them together in a very selective, very
specific way,” Bertozzi told C&EN. “That's a rare quality in a reaction.”
Credit: C&EN
The copper-catalyzed azide-alkyne cycloaddition is click chemistry's premier
reaction.
The sheer simplicity of the reaction meant that chemists embraced it
enthusiastically. By incorporating clickable azides into polymers, for example,
researchers can subsequently decorate the polymer with chemical groups that give
the material useful properties, such as electrical conductivity or protection
from ultraviolet degradation.
When Sharpless and Meldal unveiled their click reactions, Bertozzi had already
been developing bioorthogonal chemistry to help image biomolecules in living
cells. Her team was using a reaction called the Staudinger ligation, which
reacts an azide with a phosphine ester, to add fluorescent tags to sugar
molecules called glycans that are found on cell surfaces. But the reaction was
too slow for some of the imaging experiments the researchers wanted to do.
Related: 2019 Priestley Medalist K. Barry Sharpless works magic in the world of
molecules
Bertozzi wondered if click chemistry could offer a faster alternative. However,
the copper ions used in the classic click reaction are toxic to living cells,
limiting the application of this particular reaction in biology.
In 2004, Bertozzi came up with a solution: a click reaction between an azide and
a strained cyclooctyne that did not need a catalyst and therefore did not
interfere with the biochemistry of a living cell. She and her colleagues tagged
glycans on the surfaces of cells with azide groups and then used their click
reaction to couple fluorescent molecules onto those glycans so that they could
be tracked using microscopy techniques.
Collectively, these click chemistry reactions marked “the start of a completely
new chemical discipline,” Marc Robillard, CEO of Tagworks, a company that uses
click chemistry in drug delivery and radioimaging applications, told C&EN in an
email.
Since these pioneering discoveries, chemists have developed a range of click
reactions suitable for bioorthogonal chemistry. “Bioorthogonal chemistry is
baked into the fabric of chemical biology research now,” Bertozzi says.
Researchers in the biopharmaceutical industry also use bioorthogonal chemistry
to determine the biological targets of new drug molecules and to link drugs to
antibodies that can seek out particular types of cell receptors. “These are
robust, efficient reactions that always work, regardless the environment, even
in living systems,” says Petr Beier of the Institute of Organic Chemistry and
Biochemistry of the Czech Academy of Sciences, who uses click chemistry in his
research. “These reactions are key tools in our efforts to understand life.”
“Click chemistry and bioorthogonal chemistry have truly exploded in the last
couple of decades,” says José M. Mejía Oneto, founder and CEO of Shasqi, a
company conducting clinical trials of a cancer therapy that uses click chemistry
inside human patients (Bertozzi is an advisor to the company). “The elegant
simplicity and functionality of the concept has enabled countless scientists
around the world and fundamentally strengthened research, manufacturing and drug
development.”
Earlier this year, Bertozzi shared the Wolf Prize for her work on bioorthogonal
chemistry. And for Sharpless, this is the second time he has been awarded the
Nobel Prize in Chemistry. The first was in 2001, for his work on chirally
catalyzed oxidation reactions. C&EN reached his wife, Jan, shortly after the
announcement. His reaction to the news? “I guess I have to take a shower.”
Later, Sharpless told C&EN that he was still trying to wrap his head around the
idea that he had won a second Nobel Prize. Nevertheless, he says, it was
gratifying to see that click chemistry “really had a huge reach and usefulness.”
When asked how he’d celebrate, Sharpless says he is “a little bit crotchety” but
adds, “I can still go to the lab and work hard on chemistry.” He also conceded
that the department at Scripps would probably have a party, and “we're gonna get
some champagne for sure.”
Additional reporting from Bethany Halford
Chemical & Engineering News
ISSN 0009-2347
Copyright © 2022 American Chemical Society
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