Related Experiment Video
Updated: Jul 18, 2026

Sulfate Separation by Selective Crystallization with a Bis-iminoguanidinium Ligand
Published on: September 8, 2016
Chemical behavior of bis(3'-5')diguanylic acid in aqueous solutions
Mamoru Hyodo1, Yumi Sato, Yoshihiro Hayakawa
1Graduate School of Information Science/Human Informatics, and CREST/JST, Nagoya University, Chikusa, Nagoya 464-8601, Japan.
Abstract:
This paper describes unique behavior of bis(3'-5')diguanylic acid (c-di-GMP) under some conditions. Thus, c-di-GMP exists as the monomer in aprotic organic solvents such as DMSO. By contrast, c-di-GMP smoothly aggregates in water and in low-concentration aqueous solutions of some salts, such as sodium chloride and ammonium acetate, to give a mixture of many aggregates. The resulting multiple aggregates converge to the single compound (provably the monomer) in a >154 mM (0.9%) sodium chloride aqueous solution, in a >100 mM ammonium acetate buffer, and in a >100 mM phosphate buffer.
Related Concept Videos
Diazonium Group Substitution: –OH and –H
Polyprotic Acids
Acid Halides to Carboxylic Acids: Hydrolysis
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic acid...
Weak Acid Solutions
Reactions of Acid Anhydrides
Preparation of Acid Anhydrides
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...

