4'-Substituted nucleosides. 5. Hydroxymethylation of nucleoside 5'-aldehydes

Characterization of LipL as a Non-heme, Fe(II)-dependent α-Ketoglutarate:UMP Dioxygenase That Generates Uridine-5′-aldehyde during A-90289 Biosynthesis

“…S2). HPLC and LC-MS analysis with co-injections of authentic material, which was likewise previously demonstrated to be unstable upon several column purification methods (21), revealed uridine-5Ј-aldehyde was indeed the product of LipL (Fig. 2).…”

“…Uridine-5Ј-aldehyde was synthesized from uridine by protection of the 2Ј,3Ј-hydroxyl group with p-methoxybenzaldehyde, and Pfitzner-Moffatt oxidation of the resulting product provided 2Ј,3Ј-O-p-methoxybenzylideneuridine-5Ј-aldehyde; the oxidized product was deprotected to afford uridine-5Ј-aldehyde (see supplemental Methods and supplemental Fig. S2) (20,21 using an Agilent 6120 Quadrupole MSD mass spectrometer (Agilent Technologies, Santa Clara, CA) equipped with an Agilent 1200 Series Quaternary LC system and an Eclipse XDB-C18 column (250 mm ϫ 4.6 mm, 5 m, 80 Å). NMR data were collected using a Varian Unity Inova 500 MHz Spectrometer (Varian, Inc., Palo Alto, CA).…”

Synthesis and antiviral evaluation of 2-amino-1,6-dihydro-6-oxo-9-[4-bis(hydroxymethyl) -2-cyclopenten-1-yl]-9H-purine: an analog of the anti-HIV compound Carbovir

“…The oxidation of alcohol 8 using Moffatt conditions (DCC, DMSO, DCAA) was then investigated with good results. 21,22 The resulting aldehyde 9, without isolation, on aldol condensation with formaldehyde, followed by a Cannizzaro reaction provided the required 1-acetamido-4-bis(hydroxymethyl)cyclopent-2-ene (10) in 51% overall yield. Bishydroxymethyl compound 10 was deacetylated under acidic conditions and the resulting amino alcohol was coupled with 2-amino-4,6-dichloropyrimidine in the presence of diisopropylethylamine to give 11 in 50% overall yield.…”

DNA Three Way Junction Core Decorated with Amino Acids-Like Residues-Synthesis and Characterization

“…The synthesis of the key (5′S)-5′-C-propargyl-thymidine phosphoramidite 9 started from the known 3′-O-tert-butyldiphenylsilyl-thymidine aldehyde 4 [22,23] that was reacted under Barbier′s conditions with propargyl bromide to provide a 3/7 diastereoisomeric mixture of (5′R)-5′-C and (5′S)-5′-C-propargyl-thymidine 5 and 6, respectively [24,25] (Scheme 1). The separation of the diastereoisomers required a tedious HPLC process to cleanly obtain the fast moving and major compound 6.…”