16628-81-2Relevant articles and documents
Synthesis of new transglycosidically tethered 5′-nucleotides constrained to a highly biologically relevant profile
Groziak, Michael P.,Thomas, David W.
, p. 2152 - 2159 (2002)
A new motif for restricting 5′-nucleotides to highly biologically relevant conformations has been developed. The 5′,6-oxomethylene transglycosidically tethered versions of uridine 5′-monophosphate and 2′-deoxyuridine 5′-monophosphate (1 and 2, respectively) were synthesized in 10-11 steps from their respective natural nucleoside precursors along routes general to the preparation of tethered versions of a wide variety of 5′-nucleotide-based compounds. In both routes, a shelf-stable 6-hydroxymethyl pyrimidine nucleoside 5′-carboxaldehyde is the key intermediate. It exists in a carbohydrate-like fashion in a cyclic hemiacetal form under aprotic conditions. The phosphorylated cyclic hemiacetals 1 and 2 were isolated as binary mixtures of 5′-diastereomers differing principally in the trajectory of the phosphate group with respect to the carbohydrate. By 1H NMR, both 1 and 2 were demonstrated to be stable to hydrolysis at ambient temperature in D20 solution for at least 2 months. The oxomethylene transglycosidic tether as deployed in 1 and 2 leaves all of the native 5′-nucleotide molecular recognition Sites intact while it restricts the framework to a low-energy anti glycosyl conformation and an extended phosphate disposition. This provides a spatial presence that approximates nearly three-quarters of the protein-bound 5′-nucleotide ligands described in the Protein Data Bank. The tether has a low structural and electronic impact, occupies a region of space (over the β-face of the furan ring) seldom penetrated by proteins, and should be accommodated as readily on purine-based 5′-nucleotide frameworks as on pyrimidine-based ones. Because of its unique and attractive features, this new motif for the conformational restriction of 5′-nucleotides is expected to be useful for producing probes of structure/function relationships and in assessing the conformational binding requirements that enzymes and receptor sites have for their natural 5′-nucleotide-based ligands.
NOVEL COMPOUNDS AS ANTI-MYCOBACTERIALS
-
Page/Page column 55; 56, (2018/07/05)
The present disclosure relates to antibacterial compounds. In particular, the compounds are for inhibiting the growth of bacteria, particularly Mycobacterium tuberculosis (Mtb), and/or targeting bacteria having phospho-MurNAc-pentapeptidetranslocase. The present disclosure also relates to compositions containing these compounds and methods of the use of these compounds and compositions.
Straightforward synthesis of 3'-deoxy-3',4'-didehydronucleoside-5'- aldehydes via 2',3'-O-orthoester group elimination: A simple route to 3',4'-didehydronucleosides
Petrová, Magdalena,Budě?ínsky, Milo?,Rosenberg, Ivan
supporting information; experimental part, p. 6874 - 6876 (2011/03/18)
Straightforward, high-yielding syntheses of 3'-deoxy-3',4'- didehydronucleoside-5'-aldehydes and 3'-deoxy-3',4'-didehydronucleosides starting from 2',3'-O-orthoester derivatives of ribonucleosides are described.
Dinucleoside poly(borano)phosphate derivatives and uses thereof
-
Page/Page column 11, (2010/11/25)
Dinucleoside poly(borano)phosphates are provided that can be useful for prevention or treatment of diseases or disorders modulated by P2Y receptors such as type 2 diabetes, cystic fibtosis and cancer.
