Prebiotic glycosylation of uracil with electron-donating substituents.

Abstract:

:Following the suggestion that nucleoside analogues having their nucleobases joined to ribose via a carbon-carbon bond might easily arise prebiotically, the glycosylation of uracil carrying electron-donating substituents (Me, OH, OCH3, NH2) at its 5 or 6 positions was investigated. Of these, only 6-aminouracil gave glycosylated products in greater than 50% yield under simulated prebiotic conditions. The reaction provided four products, three of which were purified by preparative HPLC. The structure of the isolated compounds was determined by high-resolution mass spectrometry and NMR spectroscopy. The glycosylation products were, as expected, C-nucleosides, with the sugar having either a pyranose or a furanose structure, with the ratio depending on the precise conditions, implying reversible addition. Interestingly, the 6-aminouracil riboside displays two hydrogen bonding patterns, the "acceptor-donor-acceptor" pattern of uridine itself and (upon 180° rotation) the "acceptor-donor-donor" hydrogen bonding pattern. The second, in an artificially expanded genetic information system, is trivially called "V" and pairs with a purine analogue that presents the complementary "donor-acceptor-acceptor" hydrogen bonding pattern, trivially called "J."

journal_name

Astrobiology

journal_title

Astrobiology

authors

Kim HJ,Benner SA

doi

10.1089/ast.2014.1264

subject

Has Abstract

pub_date

2015-04-01 00:00:00

pages

301-6

issue

4

eissn

1531-1074

issn

1557-8070

journal_volume

15

pub_type

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