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(2R,4S)-2-Methyl-2,3,3,4-tetrahydroxytetrahydrofuran (M2MDB001764)

Record Information
Version2.0
Creation Date2012-07-30 14:55:30 -0600
Update Date2015-09-17 15:42:05 -0600
Secondary Accession Numbers
  • ECMDB21368
Identification
Name:(2R,4S)-2-Methyl-2,3,3,4-tetrahydroxytetrahydrofuran
Description(2R,4S)-2-methyl-2,3,3,4-tetrahydroxytetrahydrofuran, also known as autoinducer 2 (AI-2), is a member of the chemical class known as Oxolanes. These are organic compounds containing an oxolane (tetrahydrofuran) ring, which is a saturated aliphatic five-member ring containing one oxygen and five carbon atoms. AI-2 is the R isomer of 2-methyl-2,3,3,4-tetrahydroxytetrahydrofuran, so it can be abbreviated as (R)-THMF. Autoinducer 2 (AI-2), a quorum sensing signaling molecule proposed to be involved in interspecies communication, is produced by many species of gram-negative and gram-positive bacteria including E. coli. (PMID 19636340, 15601708, 18256823) AI-2 is spontaneously derived from 4,5-dihydroxy-2,3-pentanedione that, along with homocysteine, is produced by cleavage of S-adenosylhomocysteine (SAH) and S-ribosylhomocysteine by the Pfs and LuxS enzymes. (PMID 16885435) Both LsrB and Tsr are necessary for sensing AI-2. LsrB binds AI-2 in the periplasm, and Tsr is the L-serine chemoreceptor. (PMID 21097621)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (R)-THMF
  • (R)-THMF
  • AI-2
  • AI-2 (salmonella)
  • Auto inducer 2
Chemical Formula:C5H10O5
Weight:Average: 150.13
Monoisotopic: 150.052823422
InChI Key:BVIYGXUQVXBHQS-UHFFFAOYSA-N
InChI:InChI=1S/C5H10O5/c1-4(7)5(8,9)3(6)2-10-4/h3,6-9H,2H2,1H3
CAS number:Not Available
IUPAC Name:(2S,4R)-2-methyloxolane-2,3,3,4-tetrol
Traditional IUPAC Name:(2S,4R)-2-methyloxolane-2,3,3,4-tetrol
SMILES:CC1(O)OCC(O)C1(O)O
Chemical Taxonomy
Description belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentoses
Alternative Parents
Substituents
  • Pentose monosaccharide
  • Tetrahydrofuran
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carbonyl hydrate
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility766 g/LALOGPS
logP-2ALOGPS
logP-1.6ChemAxon
logS0.71ALOGPS
pKa (Strongest Acidic)9.16ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area90.15 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity30.49 m³·mol⁻¹ChemAxon
Polarizability13.34 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Water + (2R,4S)-2-Methyl-2,4-dihydroxydihydrofuran-3-one > (2R,4S)-2-Methyl-2,3,3,4-tetrahydroxytetrahydrofuran
(2R,4S)-2-methyl-2,4-dihydroxydihydrofuran-3-one + Water > (2R,4S)-2-Methyl-2,3,3,4-tetrahydroxytetrahydrofuran
(2R,4S)-2-Methyl-2,3,3,4-tetrahydroxytetrahydrofuran + Adenosine triphosphate + Water > (2R,4S)-2-Methyl-2,3,3,4-tetrahydroxytetrahydrofuran + ADP + Phosphate + Hydrogen ion
(2R,4S)-2-Methyl-2,3,3,4-tetrahydroxytetrahydrofuran + Adenosine triphosphate + Water > (2R,4S)-2-Methyl-2,3,3,4-tetrahydroxytetrahydrofuran + ADP + Phosphate + Hydrogen ion
(2R,4S)-2-methyl-2,3,3,4-tetrahydroxytetrahydrofuran + Adenosine triphosphate + (2R,4S)-2-Methyl-2,3,3,4-tetrahydroxytetrahydrofuran > Adenosine diphosphate + Hydrogen ion + (4S)-4-hydroxy-2,3-pentanedione 5-phosphate + ADP + (4S)-4-hydroxy-2,3-pentanedione 5-phosphate
(2R,4S)-2-methyl-2,3,3,4-tetrahydroxytetrahydrofuran + Phosphoribosyl-ATP + Water + (2R,4S)-2-Methyl-2,3,3,4-tetrahydroxytetrahydrofuran + Phosphoribosyl-ATP > (2R,4S)-2-methyl-2,3,3,4-tetrahydroxytetrahydrofuran + Adenosine diphosphate + Hydrogen ion + Pyrophosphate + ADP
SMPDB Pathways:
Quorum SensingPW000836 ThumbThumb?image type=greyscaleThumb?image type=simple
inner membrane transportPW000786 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-1900000000-64054e4bdfc049c7fcdbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-1900000000-4f0a98ded20b9538b158View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06r5-9100000000-feb306f4fe0457e3a763View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-3900000000-f15d2ff967a81794bcc4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000y-8900000000-6d3982661c360fcec8c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-e10480d4df1725cb9088View in MoNA
References
References:
  • Hegde, M., Englert, D. L., Schrock, S., Cohn, W. B., Vogt, C., Wood, T. K., Manson, M. D., Jayaraman, A. (2011). "Chemotaxis to the quorum-sensing signal AI-2 requires the Tsr chemoreceptor and the periplasmic LsrB AI-2-binding protein." J Bacteriol 193:768-773. Pubmed: 21097621
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Walters, M., Sircili, M. P., Sperandio, V. (2006). "AI-3 synthesis is not dependent on luxS in Escherichia coli." J Bacteriol 188:5668-5681. Pubmed: 16885435
  • Xue, T., Zhao, L., Sun, H., Zhou, X., Sun, B. (2009). "LsrR-binding site recognition and regulatory characteristics in Escherichia coli AI-2 quorum sensing." Cell Res 19:1258-1268. Pubmed: 19636340
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID448719
Kegg IDNot Available
ChemSpider ID26330266
Wikipedia IDNot Available
BioCyc IDCPD-10774
EcoCyc IDCPD-10774

Transporters

Protein Details
1. Autoinducer 2 import system permease protein lsrC
General function:
Involved in transporter activity
Specific function:
Part of the ABC transporter complex lsrABCD involved in autoinducer 2 (AI-2) import. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
lsrC
Uniprot ID:
B1XEA2
Molecular weight:
36394
Protein Details
2. Autoinducer 2 import system permease protein lsrD
General function:
Involved in transporter activity
Specific function:
Part of the ABC transporter complex lsrABCD involved in autoinducer 2 (AI-2) import. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
lsrD
Uniprot ID:
B1XEA3
Molecular weight:
34456
Protein Details
3. Autoinducer 2 import system permease protein lsrD
General function:
Involved in transporter activity
Specific function:
Part of the ABC transporter complex lsrABCD involved in autoinducer 2 (AI-2) import. Probably responsible for the translocation of the substrate across the membrane (Probable)
Gene Name:
lsrD
Uniprot ID:
P0AFS1
Molecular weight:
34456
Protein Details
4. Autoinducer 2 import system permease protein lsrC
General function:
Involved in transporter activity
Specific function:
Part of the ABC transporter complex lsrABCD involved in autoinducer 2 (AI-2) import. Probably responsible for the translocation of the substrate across the membrane (Probable)
Gene Name:
lsrC
Uniprot ID:
P77672
Molecular weight:
36394
Protein Details
5. Autoinducer 2 import ATP-binding protein LsrA
General function:
ATPase activity, coupled to transmembrane movement of substances
Specific function:
Part of the ABC transporter complex LsrABCD involved in autoinducer 2 (AI-2) import. Responsible for energy coupling to the transport system (Probable). This protein is essential for aerobic growth.
Gene Name:
lsrA
Uniprot ID:
P77257
Molecular weight:
55820
Protein Details
6. Autoinducer 2-binding protein LsrB
General function:
periplasmic space
Specific function:
Part of the ABC transporter complex LsrABCD involved in autoinducer 2 (AI-2) import. Binds AI-2 and delivers it to the LsrC and LsrD permeases (Probable).
Gene Name:
lsrB
Uniprot ID:
P76142
Molecular weight:
36684