One-Flask Syntheses of c-di-GMP and the [Rp,Rp] and [Rp,Sp] Thiophosphate Analogues
- 24 June 2010
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 12 (14) , 3269-3271
- https://doi.org/10.1021/ol101236b
Abstract
An integrated set of reactions and conditions that allow an eight-step one-flask synthesis of the protected derivatives of c-di-GMP and the [Rp,Rp] and [Rp,Sp] thiophosphate analogues is reported. Deprotection is also carried out as a one-flask procedure, with the final products isolated by crystallization from the reaction mixture. Chromatography is only used for separation of the thiophosphate diastereomers.Keywords
This publication has 21 references indexed in Scilit:
- Structural basis of ligand binding by a c-di-GMP riboswitchNature Structural & Molecular Biology, 2009
- Recognition of the bacterial second messenger cyclic diguanylate by its cognate riboswitchNature Structural & Molecular Biology, 2009
- Thiophosphate Analogs of c-di-GMP: Impact on PolymorphismNucleosides, Nucleotides and Nucleic Acids, 2009
- Riboswitches in Eubacteria Sense the Second Messenger Cyclic Di-GMPScience, 2008
- A simple solid-phase synthesis of the ubiquitous bacterial signaling molecule, c-di-GMP and analoguesMolecular BioSystems, 2008
- Roles of Cyclic Diguanylate in the Regulation of Bacterial PathogenesisAnnual Review of Microbiology, 2007
- Polymorphism of the Signaling Molecule c-di-GMPJournal of the American Chemical Society, 2006
- Cyclic di-GMP as a second messengerCurrent Opinion in Microbiology, 2006
- c-di-GMP Displays A Monovalent Metal Ion-Dependent PolymorphismJournal of the American Chemical Society, 2004
- Use of silyl ethers as fluoride scavengers in RNA synthesisTetrahedron Letters, 1999