Base-pairing of uracil and 2,6-diaminopurine: from cocrystals to photoreactivity

Stolar, Tomislav; Pearce, Ben K.D.; Etter, Martin; Truong, Khai-Nghi; Ostojić, Tea; Krajnc, Andraž; Mali, Gregor; Rossi, Barbara; Molčanov, Krešimir; Lončarić, Ivor; Meštrović, Ernest; Užarević, Krunoslav; Grisanti, Luca (2024) Base-pairing of uracil and 2,6-diaminopurine: from cocrystals to photoreactivity. iScience, 27 (6). ISSN 2589-0042

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Abstract

We show that the non-canonical nucleobase 2,6-diaminopurine (D) spontaneously base pairs with uracil (U) in water and the solid state without the need to be attached to the ribose-phosphate backbone. Depending on the reaction conditions, D and U assemble in thermodynamically stable hydrated and anhydrated D-U base-paired cocrystals. Under UV irradiation, an aqueous solution of D-U base-pair undergoes photochemical degradation, while a pure aqueous solution of U does not. Our simulations suggest that D may trigger the U photodimerization and show that complementary base-pairing modifies the photochemical properties of nucleobases, which might have implications for prebiotic chemistry.

Item Type:	Article
Uncontrolled Keywords:	Mechanochemistry; Prebiotic Chemistry; Nucleobase recognition; Photochemistry of nucleobases; UV resonance Raman spectroscopy; Solid-state reactivity
Subjects:	NATURAL SCIENCES NATURAL SCIENCES > Chemistry > Physical Chemistry NATURAL SCIENCES > Chemistry > Organic Chemistry INTERDISCIPLINARY AREAS OF KNOWLEDGE
Divisions:	Division of Physical Chemistry Theoretical Physics Division
Projects:	Project title Project leader Project code Project type Važnost mehanokemijske reaktivnosti u prebiotičkoj kemijskoj evoluciji i njezin prijenos na održivu kemijsku proizvodnju s niskim emisijama-PREBIOMECHEM Krunoslav Užarević IP-2020-02-4702 HRZZ Hibridno modeliranje pobuđenih stanja u novim molekularnim materijalima: od optičkih svojstava do dinamike ekscitona-HYMO4EXNOMOMA Luca Grisanti IP-2020-02-7262 HRZZ
Depositing User:	Krunoslav Užarević
Date Deposited:	28 Jan 2026 08:19
URI:	http://fulir.irb.hr/id/eprint/11165
DOI:	10.1016/j.isci.2024.109894

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