Autoinducer-2

Autoinducer-2

Names
Preferred IUPAC name (3aS,6S,6aR)-2,2,6,6a-Tetrahydroxy-3a-methyltetrahydro-2H-furo[2,3-d][1,3,2]dioxaborol-2-uide
Other names Dihydroxy[(2S,3R,4S)-2-methyldihydro-
Identifiers
3D model (JSmol)	Interactive image
Abbreviations	AI-2
ChEBI	CHEBI:40646 N
ChEMBL	ChEMBL1230903
ChemSpider	393894 Y
KEGG	C16421
PubChem CID	446576
CompTox Dashboard (EPA)	DTXSID201027132
InChI InChI=1S/C5H10BO7/c1-4-5(8,3(7)2-11-4)13-6(9,10)12-4/h3,7-10H,2H2,1H3/q-1/t3-,4+,5+/m0/s1 Y Key: ACKRRKSNOOISSG-VPENINKCSA-N Y InChI=1/C5H10BO7/c1-4-5(8,3(7)2-11-4)13-6(9,10)12-4/h3,7-10H,2H2,1H3/q-1/t3-,4+,5+/m0/s1 Key: ACKRRKSNOOISSG-VPENINKCBL
SMILES O[C@@H]1[C@]2(O[B-](O[C@]2(OC1)C)(O)O)O
Properties
Chemical formula	C5H10BO7
Molar mass	192.940
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Autoinducer-2 (AI-2) is a furanosyl borate diester or tetrahydroxy furan (species dependent) that—as the name suggests—is an autoinducer, a member of a family of signaling molecules used in quorum sensing.^[1] AI-2 is one of only a few known biomolecules incorporating boron. First identified in the marine bacterium Vibrio harveyi, AI-2 is produced and recognized by many Gram-negative and Gram-positive bacteria.^[2][3] AI-2 arises by the reaction of 4,5-dihydroxy-2,3-pentanedione, which is produced enzymatically, with boric acid^[4] and is recognized by the two-component sensor kinase LuxPQ in Vibrionaceae.

AI-2 is actively transported by the Lsr ABC-type transporter into the cell in Enterobacteriaceae and few other bacterial taxa such as Pasteurella, Photorhabdus, Haemophilus, and Bacillus,^[5] where it is phosphorylated by LsrK. Then, Phospho-AI-2 binds the transcriptional repressor protein, LsrR, which subsequently is released from the promoter/operator region of the lsr operon – and transcription of the lsr genes is initiated. AI-2 signalling is also regulated by glucose and cAMP/CRP via the lsr operon. In the presence of glucose, low levels of cAMP/CRP result in almost no lsr operon (lsrABCDFG) expression. Without glucose, cAMP-CRP is needed to stimulate the lsr expression, while LsrR represses its expression in the absence of the inducer, phospho-AI-2. As AI-2 accumulates, more AI-2 is taken in via LsrABCD, phosphorylated via LsrK, and the lsr transcription is de-repressed, enabling even more AI-2 uptake.^[6]

Doubts have been expressed regarding AI-2's status as a universal signal. Although the luxS gene, which encodes the protein responsible for AI-2 production is widespread, the latter has mainly a primary metabolic role in the recycling of S-adenosyl-L-methionine, with AI-2 being a by-product of that process.^[7] An unequivocally AI-2 related behavior was found to be restricted primarily to organisms bearing known AI-2 receptor genes.^[8] Thus, while it is certainly true that some bacteria respond to AI-2, it is doubtful that it is always being produced for purposes of signaling.