Proton irradiation: a key to the challenge of N-glycosidic bond formation in a prebiotic context

• Published in: Scientific reports Vol. 7; no. 1; pp. 14709 - 8
• Main Authors: Saladino, Raffaele, Bizzarri, Bruno M., Botta, Lorenzo, Šponer, Jiří, Šponer, Judit E., Georgelin, Thomas, Jaber, Maguy, Rigaud, Baptiste, Kapralov, Mikhail, Timoshenko, Gennady N., Rozanov, Alexei, Krasavin, Eugene, Timperio, Anna Maria, Mauro, Ernesto Di
• Format: Journal Article
• Language: English
• Published: London Nature Publishing Group UK 07-11-2017; Nature Publishing Group
• Subjects: 119/118; 140/131; 631/45; 639/638; Bases (nucleic acids); Chemical Sciences; Glycosylation; Humanities and Social Sciences; Irradiation; Meteors & meteorites; Mimicry; multidisciplinary; Prebiotics; Protons; Purification; Science; Science (multidisciplinary); Stereoselectivity
• ISSN: 2045-2322; 2045-2322
• DOI: 10.1038/s41598-017-15392-8

The formation of nucleosides in abiotic conditions is a major hurdle in origin-of-life studies. We have determined the pathway of a general reaction leading to the one-pot synthesis of ribo- and 2′-deoxy-ribonucleosides from sugars and purine nucleobases under proton irradiation in the presence of a chondrite meteorite. These conditions simulate the presumptive conditions in space or on an early Earth fluxed by slow protons from the solar wind, potentially mimicking a plausible prebiotic scenario. The reaction (i) requires neither pre-activated precursors nor intermediate purification/concentration steps, (ii) is based on a defined radical mechanism, and (iii) is characterized by stereoselectivity, regioselectivity and (poly)glycosylation. The yield is enhanced by formamide and meteorite relative to the control reaction.