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MetaCyc Reaction: 2.3.1.184

Superclasses: Reactions Classified By Conversion Type Simple Reactions Chemical Reactions Protein-Modification Reactions
Reactions Classified By Substrate Macromolecule Reactions Protein-Reactions Protein-Modification Reactions

EC Number: 2.3.1.184

Enzymes and Genes:
acyl-homoserine-lactone synthase Inferred from experiment : traI ( Agrobacterium fabrum C58 )

Note that this reaction equation differs from the official Enzyme Commission reaction equation for this EC number, which can be found here .

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the Enzyme Commission system.

Most BioCyc compounds have been protonated to a reference pH value of 7.3, and some reactions have been computationally balanced for hydrogen by adding free protons. Please see the PGDB Concepts Guide for more information.

Mass balance status: Balanced.

Enzyme Commission Primary Name: acyl-homoserine-lactone synthase

Enzyme Commission Synonyms: acyl-homoserine lactone synthase, acyl homoserine lactone synthase, acyl-homoserinelactone synthase, acylhomoserine lactone synthase, AHL synthase, AHS, AHSL synthase, AhyI, AinS, AinS protein, autoinducer synthase, autoinducer synthesis protein rhlI, EsaI, ExpISCC1; ExpISCC3065, LasI, LasR, LuxI, LuxI protein, LuxM, N-acyl homoserine lactone synthase, RhlI, YspI , acyl-[acyl carrier protein]:S-adenosyl-L-methionine acyltranserase (lactone-forming, methylthioadenosine-releasing)

Standard Gibbs Free Energy (ΔrG in kcal/mol): 135.14243 Inferred by computational analysis [Latendresse13]

Summary:
Acyl-homoserine lactones (AHLs) are produced by a number of bacterial species and are used by them to regulate the expression of virulence genes in a process known as quorum-sensing. Each bacterial cell has a basal level of AHL and, once the population density reaches a critical level, it triggers AHL-signaling which, in turn, initiates the expression of particular virulence genes. N-(3-oxohexanoyl)-[acyl-carrier-protein] and hexanoyl-[acyl-carrier protein] are the best substrates. The fatty-acyl substrate is derived from fatty-acid biosynthesis through acyl-[acyl-carrier-protein] rather than from fatty-acid degradation through acyl-CoA. S-adenosyl-L-methionine cannot be replaced by methionine, S-adenosylhomocysteine, homoserine or homoserine lactone.

Enzyme Commission Summary:
Acyl-homoserine lactones (AHLs) are produced by a number of bacterial species and are used by them to regulate the expression of virulence genes in a process known as quorum-sensing. Each bacterial cell has a basal level of AHL and, once the population density reaches a critical level, it triggers AHL-signaling which, in turn, initiates the expression of particular virulence genes [Parsek99]. N-(3-oxohexanoyl)-[acyl-carrier-protein] and hexanoyl-[acyl-carrier protein] are the best substrates [Schaefer96]. The fatty-acyl substrate is derived from fatty-acid biosynthesis through acyl-[acyl-carrier-protein] rather than from fatty-acid degradation through acyl-CoA [Schaefer96]. S-adenosyl-L-methionine cannot be replaced by methionine, S-adenosylhomocysteine, homoserine or homoserine lactone [Schaefer96].

Citations: [Watson01, Chakrabarti03, Hanzelka99, Ulrich04, Gould04, Raychaudhuri05, Gould06]

Gene-Reaction Schematic: ?

Relationship Links: BRENDA:EC:2.3.1.184 , ENZYME:EC:2.3.1.184 , IUBMB-ExplorEnz:EC:2.3.1.184


References

Chakrabarti03: Chakrabarti S, Sowdhamini R (2003). "Functional sites and evolutionary connections of acylhomoserine lactone synthases." Protein Eng 16(4);271-8. PMID: 12736370

Gould04: Gould TA, Schweizer HP, Churchill ME (2004). "Structure of the Pseudomonas aeruginosa acyl-homoserinelactone synthase LasI." Mol Microbiol 53(4);1135-46. PMID: 15306017

Gould06: Gould TA, Herman J, Krank J, Murphy RC, Churchill ME (2006). "Specificity of acyl-homoserine lactone synthases examined by mass spectrometry." J Bacteriol 188(2);773-83. PMID: 16385066

Hanzelka99: Hanzelka BL, Parsek MR, Val DL, Dunlap PV, Cronan JE, Greenberg EP (1999). "Acylhomoserine lactone synthase activity of the Vibrio fischeri AinS protein." J Bacteriol 181(18);5766-70. PMID: 10482519

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

Parsek99: Parsek MR, Val DL, Hanzelka BL, Cronan JE, Greenberg EP (1999). "Acyl homoserine-lactone quorum-sensing signal generation." Proc Natl Acad Sci U S A 96(8);4360-5. PMID: 10200267

Raychaudhuri05: Raychaudhuri A, Jerga A, Tipton PA (2005). "Chemical mechanism and substrate specificity of RhlI, an acylhomoserine lactone synthase from Pseudomonas aeruginosa." Biochemistry 44(8);2974-81. PMID: 15723540

Schaefer96: Schaefer AL, Val DL, Hanzelka BL, Cronan JE, Greenberg EP (1996). "Generation of cell-to-cell signals in quorum sensing: acyl homoserine lactone synthase activity of a purified Vibrio fischeri LuxI protein." Proc Natl Acad Sci U S A 93(18);9505-9. PMID: 8790360

Ulrich04: Ulrich RL (2004). "Quorum quenching: enzymatic disruption of N-acylhomoserine lactone-mediated bacterial communication in Burkholderia thailandensis." Appl Environ Microbiol 70(10);6173-80. PMID: 15466564

Watson01: Watson WT, Murphy FV, Gould TA, Jambeck P, Val DL, Cronan JE, Beck von Bodman S, Churchill ME (2001). "Crystallization and rhenium MAD phasing of the acyl-homoserinelactone synthase EsaI." Acta Crystallogr D Biol Crystallogr 57(Pt 12);1945-9. PMID: 11717525


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Fri Nov 28, 2014, BIOCYC14B.