{"id":19,"date":"2017-04-03T16:50:59","date_gmt":"2017-04-03T16:50:59","guid":{"rendered":"http:\/\/gustafsongroup.sdsu.edu\/wordpress\/?page_id=19"},"modified":"2026-01-25T23:22:01","modified_gmt":"2026-01-25T23:22:01","slug":"home","status":"publish","type":"page","link":"https:\/\/gustafsongroup.sdsu.edu\/wordpress\/index.php\/home\/","title":{"rendered":"Home"},"content":{"rendered":"\t\t
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Asymmetric Catalysis Meets Chemical Biology<\/i><\/h2>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t\t<\/div>\n\t\t<\/div>\n\t\t\t\t\t<\/div>\n\t\t<\/section>\n\t\t\t\t
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\"Gustafson
Gustafson Group Spring 2024<\/figcaption><\/figure><\/div>
\"Gustafson
Gustafson Group at ACS 2022<\/figcaption><\/figure><\/div>
\"Gustafson
Gustafson Group Celebrating Last Day of ACS 2022<\/figcaption><\/figure><\/div>
\"Gustafson
Gustafson Group at Animal Kingdom 2022<\/figcaption><\/figure><\/div>
\"Gustafson
Gustafson Group Spring 2022<\/figcaption><\/figure><\/div>
\"Gustafson
Gustafson Group Fall 2019<\/figcaption><\/figure><\/div>
\"Gustafson
Gustafson Group Tailgate 2019<\/figcaption><\/figure><\/div>
\"ACS
ACS Fall 2019<\/figcaption><\/figure><\/div>
\"UCSD
UCSD Med Chem Symposium 2019<\/figcaption><\/figure><\/div>
\"Gustafson
Gustafson Group Outing: Disneyland 2019<\/figcaption><\/figure><\/div>
\"NOS
NOS 2019<\/figcaption><\/figure><\/div>
\"SRS
SRS 2019<\/figcaption><\/figure><\/div>
\"Gustafson
Gustafson Group Fall 2018 (1)<\/figcaption><\/figure><\/div>
\"Gustafson
Gustafson Group Fall 2018 (2)<\/figcaption><\/figure><\/div>
\"Gustafson
Gustafson Group Outing: New Grads 2018<\/figcaption><\/figure><\/div>
\"Gustafson
Gustafson Group Spring 2018<\/figcaption><\/figure><\/div>
\"Gustafson
Gustafson Group 2018 Alumni<\/figcaption><\/figure><\/div>
\"Gustafson
Gustafson Group Spring 2018<\/figcaption><\/figure><\/div>
\"ACS
ACS Spring 2017<\/figcaption><\/figure><\/div>
\"Gustafson
Gustafson Group Fall 2017<\/figcaption><\/figure><\/div>
\"Gustafson
Gustafson Group Spring 2017<\/figcaption><\/figure><\/div>\t\t\t<\/div>\n\t\t\t\t\t\t\t\t\t\t\t\t
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\n\t\t\t\t\t\t\t\n\t\t\t\t\t\n\t\t\t\t\t\tTwitter<\/span>\n\t\t\t\t\t\t<\/i>\t\t\t\t\t<\/a>\n\t\t\t\t<\/span>\n\t\t\t\t\t\t\t\n\t\t\t\t\t\n\t\t\t\t\t\tInstagram<\/span>\n\t\t\t\t\t\t<\/i>\t\t\t\t\t<\/a>\n\t\t\t\t<\/span>\n\t\t\t\t\t<\/div>\n\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t\t<\/div>\n\t\t<\/div>\n\t\t\t\t\t<\/div>\n\t\t<\/section>\n\t\t\t\t
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Our lab’s research revolves around atropisomerism, a form of chirality that arises from hindered rotation about a bond. <\/span><\/p><\/blockquote>

\u00a0 \u00a0 \u00a0 \u00a0 Atropisomerism differs from other forms of chirality as racemization can occur spontaneously via bond rotation, however, when there are large groups adjacent to the axis (as is the case with the famous ligand BINAP) atropisomers can be stereochemically stable. \u00a0Atropisomerism is ubiquitous throughout drug discovery, however, is often overlooked as most examples exist as rapidly racemizing mixtures. While these molecules may be optically inactive, they will interact with their protein target in an atroposelective fashion, with the nonrelevant atropisomer contributing little to the desired activities. <\/span><\/span>At SDSU our lab has set forth to exploit atropisomerism as a design principle towards selective inhibitors of highly conserved classes of enzymes that have remained recalcitrant to selective inhibitors.<\/span><\/em><\/span>
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“Our hypothesis is that precluding the non-relevant atropisomer will result in increased target selectivity via removal of the non-target binding conformations.”<\/em><\/span><\/p><\/blockquote>\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t\t<\/div>\n\t\t<\/div>\n\t\t\t\t\t<\/div>\n\t\t<\/section>\n\t\t\t\t

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\u00a0 \u00a0 \u00a0While there are some precedents of these effects in the medicinal chemical literature, we were the first to deliberately introduce stable atropisomerism as a strategy to increase target selectivity of a promiscuous scaffold. This approach is dependent on the ability to incorporate steric bulk adjacent to the axis in order to rigidify it. This is most efficiently achieved through C-H functionalization, however, as we started these endeavors many literature methods did not prove amenable to our systems. To overcome this we developed a new Lewis base catalyzed aromatic halogenation, leading to a mild catalytic way to incorporate chlorine, and other halogens, on diverse aromatic scaffolds. This Lewis base catalysis has proved vital to our \u2018atropisomer preorganization\u2019 studies and has since been extended to other modalities including aromatic sulfenylation. Finally, we have recently begun a program within our group that focuses on atroposelective catalysis.<\/span><\/p>\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t\t<\/div>\n\t\t<\/div>\n\t\t\t\t\t<\/div>\n\t\t<\/section>\n\t\t\t\t

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\n\t\t\t\n\t\t\t\t\t\t<\/span>\n\t\t<\/div>\n\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t\t<\/div>\n\t\t<\/div>\n\t\t\t\t\t<\/div>\n\t\t<\/section>\n\t\t\t\t<\/div>\n\t\t","protected":false},"excerpt":{"rendered":"

Asymmetric Catalysis Meets Chemical Biology Gustafson Group Spring 2024 Gustafson Group at ACS 2022 Gustafson Group Celebrating Last Day of ACS 2022 Gustafson Group at Animal Kingdom 2022 Gustafson Group Spring 2022 Gustafson Group Fall 2019 Gustafson Group Tailgate 2019 ACS Fall 2019 UCSD Med Chem Symposium 2019 Gustafson Group […]<\/p>\n","protected":false},"author":1,"featured_media":0,"parent":0,"menu_order":1,"comment_status":"closed","ping_status":"closed","template":"","meta":{"footnotes":""},"class_list":["post-19","page","type-page","status-publish","hentry"],"_links":{"self":[{"href":"https:\/\/gustafsongroup.sdsu.edu\/wordpress\/index.php\/wp-json\/wp\/v2\/pages\/19","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/gustafsongroup.sdsu.edu\/wordpress\/index.php\/wp-json\/wp\/v2\/pages"}],"about":[{"href":"https:\/\/gustafsongroup.sdsu.edu\/wordpress\/index.php\/wp-json\/wp\/v2\/types\/page"}],"author":[{"embeddable":true,"href":"https:\/\/gustafsongroup.sdsu.edu\/wordpress\/index.php\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/gustafsongroup.sdsu.edu\/wordpress\/index.php\/wp-json\/wp\/v2\/comments?post=19"}],"version-history":[{"count":44,"href":"https:\/\/gustafsongroup.sdsu.edu\/wordpress\/index.php\/wp-json\/wp\/v2\/pages\/19\/revisions"}],"predecessor-version":[{"id":1667,"href":"https:\/\/gustafsongroup.sdsu.edu\/wordpress\/index.php\/wp-json\/wp\/v2\/pages\/19\/revisions\/1667"}],"wp:attachment":[{"href":"https:\/\/gustafsongroup.sdsu.edu\/wordpress\/index.php\/wp-json\/wp\/v2\/media?parent=19"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}