16178-48-6Relevant articles and documents
Concurrent Prebiotic Formation of Nucleoside-Amidophosphates and Nucleoside-Triphosphates Potentiates Transition from Abiotic to Biotic Polymerization
Arriola, Joshua T.,Jiménez, Eddy I.,Krishnamurthy, Ramanarayanan,Lin, Huacan,Müller, Ulrich F.
, (2021/11/30)
Polymerization of nucleic acids in biology utilizes 5′-nucleoside triphosphates (NTPs) as substrates. The prebiotic availability of NTPs has been unresolved and other derivatives of nucleoside-monophosphates (NMPs) have been studied. However, this latter approach necessitates a change in chemistries when transitioning to biology. Herein we show that diamidophosphate (DAP), in a one-pot amidophosphorylation-hydrolysis setting converts NMPs into the corresponding NTPs via 5′-nucleoside amidophosphates (NaPs). The resulting crude mixture of NTPs are accepted by proteinaceous- and ribozyme-polymerases as substrates for nucleic acid polymerization. This phosphorylation also operates at the level of oligonucleotides enabling ribozyme-mediated ligation. This one-pot protocol for simultaneous generation of NaPs and NTPs suggests that the transition from prebiotic-phosphorylation and oligomerization to an enzymatic processive-polymerization can be more continuous than previously anticipated.
A Modular Synthesis of Modified Phosphoanhydrides
Hofer, Alexandre,Cremosnik, Gregor S.,Müller, Andr C.,Giambruno, Roberto,Trefzer, Claudia,Superti-Furga, Giulio,Bennett, Keiryn L.,Jessen, Henning J.
supporting information, p. 10116 - 10122 (2015/07/07)
Phosphoanhydrides (P-anhydrides) are ubiquitously occurring modifications in nature. Nucleotides and their conjugates, for example, are among the most important building blocks and signaling molecules in cell biology. To study and manipulate their biological functions, a diverse range of analogues have been developed. Phosphate-modified analogues have been successfully applied to study proteins that depend on these abundant cellular building blocks, but very often both the preparation and purification of these molecules are challenging. This study discloses a general access to P-anhydrides, including different nucleotide probes, that greatly facilitates their preparation and isolation. The convenient and scalable synthesis of, for example, 18O labeled nucleoside triphosphates holds promise for future applications in phosphoproteomics. Building the building blocks: This study discloses a general method for the functionalization of unprotected nucleotides and sugar phosphates with P-amidites in a highly modular way. The strategy facilitates the preparation of thiophosphate-containing nucleotides, 18O-labeled nucleoside triphosphates, and farnesylated nucleotides, as well as a range of dinucleoside polyphosphates and nucleotide sugars.
A P(V)-N activation strategy for the synthesis of nucleoside polyphosphates
Sun, Qi,Gong, Shanshan,Sun, Jian,Liu, Si,Xiao, Qiang,Pu, Shouzhi
, p. 8417 - 8426 (2013/09/24)
A general and high-yielding synthesis of nucleoside 5′-triphosphates (NTPs) and nucleoside 5′-diphosphates (NDPs) from protected nucleoside 5′-phosphoropiperidates promoted by 4,5-dicyanoimidazole (DCI) has been developed. 31P NMR tracing experiments showed that the sequential deprotection and coupling reactions were exceptionally clean. The phosphoropiperidate exhibited superior reactivity to the conventional phosphoromorpholidate toward DCI-promoted NTP/NDP synthesis. The experimental results suggested that the mechanism of DCI activation could be distinctive for NTP and NDP synthesis, depending on the different nucleophilicity of pyrophosphate and phosphate.
