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Synlett 2018; 29(06): 699-713
DOI: 10.1055/s-0036-1591922
DOI: 10.1055/s-0036-1591922
account
The Hitchhiker’s Guide to Organophosphate Chemistry
Our research is supported by the German Science Foundation (DFG, Grants JE 572/4-1 & Inst39/1056-1 FUGG), the Human Frontier Science Program Organization (HFSP, Grant RGP0025/2016), the Volkswagen Foundation (Experiment!), the Carl-Zeiss Foundation (Rückkehrprogramm GSO), the Swiss National Science Foundation (SNSF, PP00P2_157607), and the Chinese Scholarship Council.
Further Information
Publication History
Received: 20 December 2017
Accepted after revision: 11 January 2018
Publication Date:
09 February 2018 (online)
Abstract
Phosphate esters and anhydrides are abundant motifs in biologically important molecules. Their chemical synthesis, modification, and purification are still challenging tasks often restricted to specialized laboratories. The isolation and analytical characterization of novel highly charged (poly)phosphorylated natural products comes with many challenges but also opportunities. Understanding the in vivo function of such molecules is another central endeavor. More often than not, studies into the function of charged metabolites are hampered by insufficient cellular uptake and thus delivery technologies are in high demand. Overall, research in this field requires several complementary approaches. This account discusses selected examples of some emerging technologies in organophosphate chemistry, with a focus on recent achievements in the authors laboratory usually in the context of diverse collaborative efforts.
1 Prologue
2 Introduction
3 The Inositol Phosphates and Pyrophosphates
3.1 Novel Synthetic Approaches
3.2 Stereochemical Assignment
3.3 A Protecting Group Concept for Phosphates
3.4 Cellular Delivery
3.5 Selected Examples of New Biology
4 Nucleotides
4.1 Iterative Phosphorylation
4.2 Bidirectional Phosphorylation
5 Conclusion
6 Outlook
-
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