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 '-deoxyribonucleosides 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.
Saladino, R., Bizzarri, B.m., Botta, L., Sponer, J., Sponer, J.e., Georgelin, T., et al. (2017). Proton irradiation: A key to the challenge of N-glycosidic bond formation in a prebiotic context. SCIENTIFIC REPORTS, 7(1), 14709 [10.1038/s41598-017-15392-8].
Proton irradiation: A key to the challenge of N-glycosidic bond formation in a prebiotic context
Botta L.;
2017-01-01
Abstract
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 '-deoxyribonucleosides 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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
