Syntheses of 5'-Nucleoside Monophosphate Derivatives with Unique Aminal, Hemiaminal, and Hemithioaminal Functionalities: A New Class of 5'-Peptidyl Nucleotides
| Autor: | Piet Herdewijn, Elisabetta Groaz, Lia Margamuljana, Swarup De |
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| Rok vydání: | 2016 |
| Předmět: |
nucleosides
peptides phosphoaminals polymerase chain reaction synthetic biology Stereochemistry 010402 general chemistry 01 natural sciences Pyrophosphate Polymerase Chain Reaction Catalysis Residue (chemistry) chemistry.chemical_compound Synthetic biology Nucleotide Phosphoamino Acids chemistry.chemical_classification 010405 organic chemistry Chemistry Organic Chemistry Nucleosides General Chemistry DNA Polymerase I 0104 chemical sciences Kinetics Aminal Hemiaminal Peptides Linker DNA |
| Zdroj: | Chemistry (Weinheim an der Bergstrasse, Germany). 22(24) |
| ISSN: | 1521-3765 |
| Popis: | A number of synthetically useful transformations have been developed to generate novel 5'-peptidyl nucleoside monophosphate analogues that incorporate sensitive phosphoaminal, -hemiaminal or -hemithioaminal functionalities. The strategies adopted entailed the coupling between dipeptides, which enclose a reactive Cα-functionalized glycine residue and phosphate or phosphorothioate moieties. These developments led to potentially powerful and general methodologies for the preparation of α-phosphorylated pseudopeptides as well as nucleoside monophosphate mimics. The resulting conjugates are of interest for a variety of important applications, which range from drug development to synthetic biology, as pronucleotides or artificial building blocks for the enzymatic synthesis of xenobiotic information systems. The potential of all dipeptide-TMP conjugates as pyrophosphate mimics in the DNA polymerization reaction was tested, and the influence of the nature of the linker was evaluated by in vitro chain elongation assay in the presence of wild-type microbial DNA polymerases. ispartof: Chemistry - a European Journal vol:22 issue:24 pages:8167-8180 ispartof: location:Germany status: published |
| Databáze: | OpenAIRE |
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