MetaCyc Compound: (2S,4S)-2-methyl-2,4-dihydroxydihydrofuran-3-one

Synonyms: Pro-AI-2 (vibrio), (S)-DHMF

Citations: [Miller04a, Chen02]

Chemical Formula: C5H8O4

Molecular Weight: 132.12 Daltons

Monoisotopic Molecular Weight: 132.0422587452 Daltons

(2S,4S)-2-methyl-2,4-dihydroxydihydrofuran-3-one compound structure


InChI: InChI=1S/C5H8O4/c1-5(8)4(7)3(6)2-9-5/h3,6,8H,2H2,1H3/t3-,5-/m0/s1


Unification Links: ChemSpider:8416322 , PubChem:10240835

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -55.991043 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

autoinducer AI-2 biosynthesis II (Vibrio) :
(2S,4S)-2-methyl-2,4-dihydroxydihydrofuran-3-one + H2O → (2S,4S)-2-methyl-2,3,3,4-tetrahydroxytetrahydrofuran

Reactions known to produce the compound:

autoinducer AI-2 biosynthesis II (Vibrio) :
autoinducer 2 → (2S,4S)-2-methyl-2,4-dihydroxydihydrofuran-3-one


Chen02: Chen X, Schauder S, Potier N, Van Dorsselaer A, Pelczer I, Bassler BL, Hughson FM (2002). "Structural identification of a bacterial quorum-sensing signal containing boron." Nature 415(6871);545-9. PMID: 11823863

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Miller04a: Miller ST, Xavier KB, Campagna SR, Taga ME, Semmelhack MF, Bassler BL, Hughson FM (2004). "Salmonella typhimurium recognizes a chemically distinct form of the bacterial quorum-sensing signal AI-2." Mol Cell 15(5);677-87. PMID: 15350213

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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