Fluorination Influences the Bioisostery of Myo‐Inositol Pyrophosphate Analogs

Inositol pyrophosphates (PP−IPs) are densely phosphorylated messenger molecules involved in numerous biological processes. PP−IPs contain one or two pyrophosphate group(s) attached to a phosphorylated myo‐inositol ring. 5PP−IP5 is the most abundant PP−IP in human cells. To investigate the function a...

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Published in	Chemistry : a European journal Vol. 29; no. 67; pp. e202302426 - n/a
Main Authors	Hostachy, Sarah, Wang, Huanchen, Zong, Guangning, Franke, Katy, Riley, Andrew M., Schmieder, Peter, Potter, Barry V. L., Shears, Stephen B., Fiedler, Dorothea
Format	Journal Article
Language	English
Published	WEINHEIM Wiley 01.12.2023 Wiley Subscription Services, Inc
Subjects	Analogs Biological activity Chemistry Chemistry, Multidisciplinary Crystallization Diphosphates Fluorination fluorine Halogenation Humans Inositol Inositol Phosphates - chemistry inositol pyrophosphates Inositols Kinases phosphoramidite Phosphorylation Physical Sciences protein structures Pyrophosphates Reagents Science & Technology Synthesis DIPHOSPHOINOSITOL PENTAKISPHOSPHATE phosphoramidite METABOLISM inositol pyrophosphates KINASE protein structures POLYPHOSPHATES phosphorylation EUKARYOTIC PHOSPHATE HOMEOSTASIS fluorine
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Abstract	Inositol pyrophosphates (PP−IPs) are densely phosphorylated messenger molecules involved in numerous biological processes. PP−IPs contain one or two pyrophosphate group(s) attached to a phosphorylated myo‐inositol ring. 5PP−IP5 is the most abundant PP−IP in human cells. To investigate the function and regulation by PP−IPs in biological contexts, metabolically stable analogs have been developed. Here, we report the synthesis of a new fluorinated phosphoramidite reagent and its application for the synthesis of a difluoromethylene bisphosphonate analog of 5PP−IP5. Subsequently, the properties of all currently reported analogs were benchmarked using a number of biophysical and biochemical methods, including co‐crystallization, ITC, kinase activity assays and chromatography. Together, the results showcase how small structural alterations of the analogs can have notable effects on their properties in a biochemical setting and will guide in the choice of the most suitable analog(s) for future investigations. How do pyrophosphate analogs compare? The synthesis of a fluorinated analog of an inositol pyrophosphate messenger is reported. Comparison of the physicochemical and biochemical properties of a range of closely related analogs showcases that subtle modifications can distinctly influence the behavior of molecules.
AbstractList	Inositol pyrophosphates (PP−IPs) are densely phosphorylated messenger molecules involved in numerous biological processes. PP−IPs contain one or two pyrophosphate group(s) attached to a phosphorylated myo‐inositol ring. 5PP−IP5 is the most abundant PP−IP in human cells. To investigate the function and regulation by PP−IPs in biological contexts, metabolically stable analogs have been developed. Here, we report the synthesis of a new fluorinated phosphoramidite reagent and its application for the synthesis of a difluoromethylene bisphosphonate analog of 5PP−IP5. Subsequently, the properties of all currently reported analogs were benchmarked using a number of biophysical and biochemical methods, including co‐crystallization, ITC, kinase activity assays and chromatography. Together, the results showcase how small structural alterations of the analogs can have notable effects on their properties in a biochemical setting and will guide in the choice of the most suitable analog(s) for future investigations. How do pyrophosphate analogs compare? The synthesis of a fluorinated analog of an inositol pyrophosphate messenger is reported. Comparison of the physicochemical and biochemical properties of a range of closely related analogs showcases that subtle modifications can distinctly influence the behavior of molecules. Inositol pyrophosphates (PP−IPs) are densely phosphorylated messenger molecules involved in numerous biological processes. PP−IPs contain one or two pyrophosphate group(s) attached to a phosphorylated myo‐inositol ring. 5PP−IP5 is the most abundant PP−IP in human cells. To investigate the function and regulation by PP−IPs in biological contexts, metabolically stable analogs have been developed. Here, we report the synthesis of a new fluorinated phosphoramidite reagent and its application for the synthesis of a difluoromethylene bisphosphonate analog of 5PP−IP5. Subsequently, the properties of all currently reported analogs were benchmarked using a number of biophysical and biochemical methods, including co‐crystallization, ITC, kinase activity assays and chromatography. Together, the results showcase how small structural alterations of the analogs can have notable effects on their properties in a biochemical setting and will guide in the choice of the most suitable analog(s) for future investigations. Inositol pyrophosphates (PP-IPs) are densely phosphorylated messenger molecules involved in numerous biological processes. PP-IPs contain one or two pyrophosphate group(s) attached to a phosphorylated myo-inositol ring. 5PP-IP5 is the most abundant PP-IP in human cells. To investigate the function and regulation by PP-IPs in biological contexts, metabolically stable analogs have been developed. Here, we report the synthesis of a new fluorinated phosphoramidite reagent and its application for the synthesis of a difluoromethylene bisphosphonate analog of 5PP-IP5. Subsequently, the properties of all currently reported analogs were benchmarked using a number of biophysical and biochemical methods, including co-crystallization, ITC, kinase activity assays and chromatography. Together, the results showcase how small structural alterations of the analogs can have notable effects on their properties in a biochemical setting and will guide in the choice of the most suitable analog(s) for future investigations. Inositol pyrophosphates (PP-IPs) are densely phosphorylated messenger molecules involved in numerous biological processes. PP-IPs contain one or two pyrophosphate group(s) attached to a phosphorylated myo-inositol ring. 5PP-IP is the most abundant PP-IP in human cells. To investigate the function and regulation by PP-IPs in biological contexts, metabolically stable analogs have been developed. Here, we report the synthesis of a new fluorinated phosphoramidite reagent and its application for the synthesis of a difluoromethylene bisphosphonate analog of 5PP-IP . Subsequently, the properties of all currently reported analogs were benchmarked using a number of biophysical and biochemical methods, including co-crystallization, ITC, kinase activity assays and chromatography. Together, the results showcase how small structural alterations of the analogs can have notable effects on their properties in a biochemical setting and will guide in the choice of the most suitable analog(s) for future investigations. Abstract Inositol pyrophosphates (PP−IPs) are densely phosphorylated messenger molecules involved in numerous biological processes. PP−IPs contain one or two pyrophosphate group(s) attached to a phosphorylated myo‐inositol ring. 5PP−IP 5 is the most abundant PP−IP in human cells. To investigate the function and regulation by PP−IPs in biological contexts, metabolically stable analogs have been developed. Here, we report the synthesis of a new fluorinated phosphoramidite reagent and its application for the synthesis of a difluoromethylene bisphosphonate analog of 5PP−IP 5 . Subsequently, the properties of all currently reported analogs were benchmarked using a number of biophysical and biochemical methods, including co‐crystallization, ITC, kinase activity assays and chromatography. Together, the results showcase how small structural alterations of the analogs can have notable effects on their properties in a biochemical setting and will guide in the choice of the most suitable analog(s) for future investigations.
Author	Schmieder, Peter Potter, Barry V. L. Wang, Huanchen Shears, Stephen B. Franke, Katy Fiedler, Dorothea Riley, Andrew M. Zong, Guangning Hostachy, Sarah
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Keywords	DIPHOSPHOINOSITOL PENTAKISPHOSPHATE phosphoramidite METABOLISM inositol pyrophosphates KINASE protein structures POLYPHOSPHATES phosphorylation EUKARYOTIC PHOSPHATE HOMEOSTASIS fluorine
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Snippet	Inositol pyrophosphates (PP−IPs) are densely phosphorylated messenger molecules involved in numerous biological processes. PP−IPs contain one or two... Inositol pyrophosphates (PP-IPs) are densely phosphorylated messenger molecules involved in numerous biological processes. PP-IPs contain one or two... Abstract Inositol pyrophosphates (PP−IPs) are densely phosphorylated messenger molecules involved in numerous biological processes. PP−IPs contain one or two...
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SubjectTerms	Analogs Biological activity Chemistry Chemistry, Multidisciplinary Crystallization Diphosphates Fluorination fluorine Halogenation Humans Inositol Inositol Phosphates - chemistry inositol pyrophosphates Inositols Kinases phosphoramidite Phosphorylation Physical Sciences protein structures Pyrophosphates Reagents Science & Technology Synthesis
Title	Fluorination Influences the Bioisostery of Myo‐Inositol Pyrophosphate Analogs
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