Thomas R. Webb

The direct conversion of 5'-O-trityl-3'-keto-2'-deoxythymidine to 1-(2-deoxy-3-methyl-beta-D-xylosyl)thymine

The first synthesis of 1-(2-deoxy-3-methyl-beta-D-xylosyl)thymine from the unstable 5′-O-trityl-3′-keto-2′-deoxythymidine via a novel organometallic reagent is reported. The stereochemistry at the 3′ position is conclusively determined by chemical means. Some further transformations of the title product are described.

Regioselective synthesis of 2-substituted pyridines via grignard addition to 1-(alkoxycarboxy)-pyridinium salts

Abstract A regioselective one pot synthesis of 2-substituted pyridine derivatives from pyridine-1-oxides is described.

Synthesis and crosslinking properties of a deoxyoligonucleotide containing N6,N6-ethanodeoxyadenosine

Abstract We report the synthesis of 5′ HO-dT6(N6,N6-ethanodeoxyadenosine)T14. This oligonucleotide specifically crosslinks with 5′ HO-dA14CA6T at pH 7.5 and 20°C with a half-life of approximately one day.

A Simple Synthesis of 5-Amino-4-imidazolecarboxamide Riboside-5′-Tri-Phosphate: The Proposed Alarmone for 10-Formyl-tetrahydrofolate Deficiency

Abstract A short synthesis of the title compound (1) from the nucleo-side, 5-amino-4-imidazolecarboxamide riboside (2), is reported, Treatment of 2 with phosphorus oxychloride (POCl3) in trimethyl phosphate (PO(OCH3)3), followed by the addition of bis-tri-n-butylammonium pyrophosphate and finally hydrolysis, gave 1 in good overall yield. This synthesis confirms the structure of 1 as proposed and further demonstrates the utility of this triphosphorylation procedure.