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Although nucleic acids can assemble into programmable nanostructures through base\u2010pairing interactions, their chemical diversity is limited to four nucleobases. DNA amphiphiles overcome this limitation by introducing orthogonal interactions through non\u2010nucleosidic modifications. These amphiphiles self\u2010assemble into diverse morphologies, such as spheres, fibers, or sheets, with closely packed, parallel DNA strands on their exterior. This unusual arrangement can give rise to emergent properties absent in simple DNA strands. Here, we show that the precise sequence of single\u2010stranded DNA, independent of double helix base\u2010pairing, can be used to program the self\u2010assembled morphology of DNA amphiphiles. Remarkably, small sequence variations can drive the formation of nonequilibrium DNA nanotoroids, rather than conventional morphologies. The DNA nanotoroids were formed as on\u2010pathway structures via a competitive mechanism, only when a toroid\u2010selective DNA sequence was used. They could be stabilized noncovalently by a small molecule cross\u2010linker or coassembly with a secondary DNA amphiphile. Molecular dynamics simulations demonstrated the dependence of toroid formation on the structure of the end \u03c0\u2010stacking unit. This work introduces a new class of DNA\u2010based nanotoroid materials with assembly properties controlled by unique sequences, akin to proteins, for applications in cell delivery, nanofiltration, nanoreactors, and materials templation.<\/jats:p>","DOI":"10.1002\/anie.202501441","type":"journal-article","created":{"date-parts":[[2025,6,14]],"date-time":"2025-06-14T15:44:47Z","timestamp":1749915887000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Complex Donuts: Small Variations in DNA Sequence Dictate Pathway Complexity in DNA Nanotoroids"],"prefix":"10.1002","volume":"64","author":[{"given":"Muhammad Ghufran","family":"Rafique","sequence":"first","affiliation":[{"name":"Department of Chemistry McGill University  801 Sherbrooke St W Montr\u00e9al QC H3A 0B8 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yihao","family":"Wu","sequence":"additional","affiliation":[{"name":"Department of Chemistry McGill University  801 Sherbrooke St W Montr\u00e9al QC H3A 0B8 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yutong","family":"Shi","sequence":"additional","affiliation":[{"name":"Borch Department of Medicinal Chemistry and Molecular Pharmacology Purdue University  West Lafayette IN 47906 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Quentin","family":"Laurent","sequence":"additional","affiliation":[{"name":"Department of Chemistry McGill University  801 Sherbrooke St W Montr\u00e9al QC H3A 0B8 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Abdelrahman","family":"Elmanzalawy","sequence":"additional","affiliation":[{"name":"Department of Chemistry McGill University  801 Sherbrooke St W Montr\u00e9al QC H3A 0B8 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Christopher","family":"Saab","sequence":"additional","affiliation":[{"name":"Department of Chemistry McGill University  801 Sherbrooke St W Montr\u00e9al QC H3A 0B8 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yu","family":"Shi","sequence":"additional","affiliation":[{"name":"Borch Department of Medicinal Chemistry and Molecular Pharmacology Purdue University  West Lafayette IN 47906 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dmytro F.","family":"Perepichka","sequence":"additional","affiliation":[{"name":"Department of Chemistry McGill University  801 Sherbrooke St W Montr\u00e9al QC H3A 0B8 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jianing","family":"Li","sequence":"additional","affiliation":[{"name":"Borch Department of Medicinal Chemistry and Molecular Pharmacology Purdue University  West Lafayette IN 47906 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5100-0532","authenticated-orcid":false,"given":"Hanadi F.","family":"Sleiman","sequence":"additional","affiliation":[{"name":"Department of Chemistry McGill University  801 Sherbrooke St W Montr\u00e9al QC H3A 0B8 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,7,4]]},"reference":[{"key":"e_1_2_7_1_1","volume-title":"Biochemistry","author":"Berg J. 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