4,5-Dihydroxy-2,3-pentanedione

4,5-Dihydroxy-2,3-pentanedione

Names
Other names 1-Deoxypento-2,4-diulose; 1-Deoxypentosone; Dihydroxy-2,3-pentanedione, DPD
Identifiers
CAS Number	142937-55-1
Properties
Chemical formula	C5H8O4
Molar mass	132.12 g·mol^−1
Appearance	Colorless
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

4,5-Dihydroxy-2,3-pentanedione (DPD) is an organic compound that occurs naturally but exists as several related structures. The idealized formula for this species is CH₃C(O)C(O)CH(OH)CH₂OH, but it is known to exist as several other forms resulting from cyclization. It is not stable at room temperature as a pure material, which has further complicated its analysis. The (S)-stereoisomer occurs naturally. It is typically hydrated, i.e., one keto group has added water to give the geminal diol.

DPD is produced by degradation of S-adenosylhomocysteine by the action of the enzyme S-ribosylhomocysteinase.^[1] The compound probably does not exist as depicted above, but as an equilibrium mixture of three hydrates.

Hydrated derivatives of dihydroxypentanedione.^[2]

DPD is a precursor to borate diester, which is known as autoinducer-2 (AI-2). AI-2 is a signaling molecules found in quorum sensing. It is produced and recognized by many Gram-negative and Gram-positive bacteria.^[3][4] AI-2 is synthesized by the reaction of 1-deoxy-3-dehydro-D-ribulose with boric acid ^[5] and is recognized by the two-component sensor kinase LuxPQ in Vibrionaceae.

References

1. Jinge Zhu, Eric Dizin, Xubo Hu, Anne-Sophie Wavreille, Junguk Park, Dehua Pei "S-Ribosylhomocysteinase (LuxS) Is a Mononuclear Iron Protein" Biochemistry, 2003, volume 42, pp 4717–4726. doi:10.1021/bi034289j
2. Roberta J. Worthington and Christian Melander "Deconvoluting Interspecies Bacterial Communication" Angew. Chem. Int. Ed. 2012, volume 51, 6314 – 6315. doi:10.1002/anie.201202440
3. Miller, Stephen T.; Xavier, Karina B.; Campagna, Shawn R.; Taga, Michiko E.; Semmelhack, Martin F.; Bassler, Bonnie L.; Hughson, Frederick M. (2004). "Salmonella typhimurium Recognizes a Chemically Distinct Form of the Bacterial Quorum-Sensing Signal AI-2". Molecular Cell 15 (5): 677–687. doi:10.1016/j.molcel.2004.07.020. PMID 15350213.
4. Miller, M. B.; Bassler, B. L. (2001). "Quorum sensing in bacteria". Annual Review of Microbiology 55: 165–199. doi:10.1146/annurev.micro.55.1.165. PMID 11544353.
5. http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/misc/AI2.html