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{{chembox |
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{{chembox |
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| verifiedrevid = 411782715 |
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| verifiedrevid = 443726649 |
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|ImageFile=Enterobactin.svg |
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| ImageFile=Enterobactin.svg |
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|ImageSize=250 |
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| ImageSize=250 |
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|IUPACName=''N,N',N''''-((3''S'',7''S'',11''S'')-2,6,10- trioxo-1,5,9-trioxacyclododecane- 3,7,11-triyl)tris(2,3-dihydroxybenzamide) |
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| PIN=''N'',''N''′,''N''′′-tris(2,3-dihydroxybenzamide) |
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|OtherNames= |
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| OtherNames= |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| InChI = 1/C30H27N3O15/c34-19-7-1-4-13(22(19)37)25(40)31-16-10-46-29(44)18(33-27(42)15-6-3-9-21(36)24(15)39)12-48-30(45)17(11-47-28(16)43)32-26(41)14-5-2-8-20(35)23(14)38/h1-9,16-18,34-39H,10-12H2,(H,31,40)(H,32,41)(H,33,42)/t16-,17-,18-/m0/s1 |
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| InChI = 1/C30H27N3O15/c34-19-7-1-4-13(22(19)37)25(40)31-16-10-46-29(44)18(33-27(42)15-6-3-9-21(36)24(15)39)12-48-30(45)17(11-47-28(16)43)32-26(41)14-5-2-8-20(35)23(14)38/h1-9,16-18,34-39H,10-12H2,(H,31,40)(H,32,41)(H,33,42)/t16-,17-,18-/m0/s1 |
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| InChIKey = SERBHKJMVBATSJ-BZSNNMDCBT |
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| InChIKey = SERBHKJMVBATSJ-BZSNNMDCBT |
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| SMILES1 = c1cc(c(c(c1)O)O)C(=O)N2COC(=O)(COC(=O)(COC2=O)NC(=O)c3cccc(c3O)O)NC(=O)c4cccc(c4O)O |
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| SMILES1 = c1cc(c(c(c1)O)O)C(=O)N2COC(=O)(COC(=O)(COC2=O)NC(=O)c3cccc(c3O)O)NC(=O)c4cccc(c4O)O |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = SERBHKJMVBATSJ-BZSNNMDCSA-N |
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| StdInChIKey = SERBHKJMVBATSJ-BZSNNMDCSA-N |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo=28384-96-5 |
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| CASNo=28384-96-5 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem=34231 |
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| UNII = 35C9R2N24F |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| PubChem=34231 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 31543 |
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| ChemSpiderID = 31543 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 28855 |
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| ChEBI = 28855 |
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| SMILES=C1C(C(=O)OCC(C(=O)OCC(C(=O)O1)NC(=O)C2=C(C(=CC=C2)O)O)NC(=O)C3=C(C(=CC=C3)O)O)NC(=O)C4=C(C(=CC=C4)O)O |
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| SMILES=C1C(C(=O)OCC(C(=O)OCC(C(=O)O1)NC(=O)C2=C(C(=CC=C2)O)O)NC(=O)C3=C(C(=CC=C3)O)O)NC(=O)C4=C(C(=CC=C4)O)O |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>30</sub>H<sub>27</sub>N<sub>3</sub>O<sub>15</sub> |
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| Formula=C<sub>30</sub>H<sub>27</sub>N<sub>3</sub>O<sub>15</sub> |
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| MolarMass=669.55 g/mol |
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| MolarMass=669.55 g/mol |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| FlashPt= |
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'''Enterobactin (also known as Enterochelin)''' is a high affinity ] that acquires ] for microbial systems. It is primarily found in ] bacteria, such as '']'' and '']''.<ref>{{cite journal | author = Dertz, Emily A., Jide Xu, Alain Stintzi, and Kenneth N. Raymond | title = Bacillibactin-Mediated Iron Transport in Bacillus Subtilis | journal = ] | volume = 128 | year = 2006 | pages = 22–23 | doi = 10.1021/ja055898c | pmid = 16390102 | issue = 1}}</ref> |
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'''Enterobactin''' (also known as '''enterochelin''') is a high affinity ] that acquires ] for microbial systems. It is primarily found in ] bacteria, such as '']'' and '']''.<ref>{{cite journal | vauthors = Dertz EA, Xu J, Stintzi A, Raymond KN | title = Bacillibactin-mediated iron transport in Bacillus subtilis | journal = Journal of the American Chemical Society | volume = 128 | issue = 1 | pages = 22–3 | date = January 2006 | pmid = 16390102 | doi = 10.1021/ja055898c }}</ref> |
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Enterobactin is the strongest siderophore known, binding to the ferric ion (Fe<sup>3+</sup>) with the ] (K = 10<sup>52</sup> M<sup>−1</sup>).<ref>{{cite journal | author = Carrano, Carl J., and Kenneth N. Raymond | title = Ferric Ion Sequestering Agents. 2. Kinetics and Mechanism of Iron Removal From Transferrin by Enterobactin and Synthetic Tricatechols | journal = ] | volume = 101 | year = 1979 | pages = 5401–5404 | doi = 10.1021/ja00512a047}}</ref> This value is substantially larger than even some synthetic metal ]s, such as ] (K<sub>f,Fe3+</sub> ~ 10<sup>25</sup> M<sup>−1</sup>). <sup></sup> Due to its high affinity, enterobactin is capable of ] even in environments where the concentration of ferric ion is held very low, such as within living organisms. ]ic ] can steal iron from other living organisms using this mechanism, even though the concentration of iron is kept extremely low due to the toxicity of free iron. |
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Enterobactin is the strongest siderophore known, binding to the ferric ion (Fe<sup>3+</sup>) with ] K = 10<sup>52</sup> M<sup>−1</sup>.<ref name=Carrano1979 /> This value is substantially larger than even some synthetic metal ]s, such as ] (K<sub>f,Fe3+</sub> ~ 10<sup>25</sup> M<sup>−1</sup>).<ref name=Walsh1990 /> Due to its high affinity, enterobactin is capable of ] even in environments where the concentration of ferric ion is held very low, such as within living organisms. ]ic ] can steal iron from other living organisms using this mechanism, even though the concentration of iron is kept extremely low due to the toxicity of free iron. |
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==Structure and biosynthesis== |
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==Structure and biosynthesis== |
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], an aromatic ] ], is converted to ] (DHB) by a series of ]s, EntA, EntB and EntC. An ] linkage of DHB to ] is then catalyzed by EntD, EntE, EntF and EntB. Three molecules of the DHB-Ser formed undergo ], yielding enterobactin. <sup></sup> Whereas a number of possible ]s are possible due to the ] of the serine residues, only the Δ-cis ] is metabolically active.<ref>{{cite journal | author = Walsh, Christopher T., Jun Liu, Frank Rusnak, and Masahiro Sakaitani | title = Molecular Studies on Enzymes in Chorismate Metabolism and the Enterobactin Biosynthetic Pathway | journal = ] | volume = 90 | year = 1990 | pages = 1105–1129 | doi = 10.1021/cr00105a003}}</ref> |
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], an ] ], is converted to ] (DHB) by a series of ]s, EntA, EntB and EntC. An ] linkage of DHB to ] is then catalyzed by EntD, EntE, EntF and EntB. Three molecules of the DHB-Ser formed undergo ], yielding enterobactin.<ref name=Raymond2003 /> Although a number of ]s are possible due to the ] of the serine residues, only the Δ-cis ] is metabolically active.<ref name=Walsh1990 /> The first three-dimensional structure of a metal enterobactin complex was determined as the ](IV) complex.<ref name=Karpishin1992 /> Although ferric enterobactin long eluded crystallization, its definitive three-dimensional structure was ultimately obtained using racemic crystallography, in which crystals of a 1:1 mixture of ferric enterobactin and its mirror image (ferric enantioenterobactin) were grown and analyzed by X-ray crystallography.<ref>{{cite journal | vauthors = Johnstone TC, Nolan EM | title = Determination of the Molecular Structures of Ferric Enterobactin and Ferric Enantioenterobactin Using Racemic Crystallography | journal = Journal of the American Chemical Society | volume = 139 | issue = 42 | pages = 15245–15250 | date = October 2017 | pmid = 28956921 | pmc = 5748154 | doi = 10.1021/jacs.7b09375 }}</ref> |
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]<ref>{{Citation |last=Raines |first=D. J. |title=Siderophores |date=2015-01-01 |work=Reference Module in Chemistry, Molecular Sciences and Chemical Engineering |url=https://www.sciencedirect.com/science/article/pii/B9780124095472110406 |access-date=2024-07-06 |publisher=Elsevier |isbn=978-0-12-409547-2 |last2=Sanderson |first2=T. J. |last3=Wilde |first3=E. J. |last4=Duhme-Klair |first4=A. -K.}}</ref>]] |
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==Mechanism== |
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==Mechanism== |
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] in bacterial cells triggers secretion of enterobactin into the extracellular environment, causing formation of an ] "]" wherein ferric ion is chelated to the conjugate base of enterobactin. In '']'', FepA in the bacterial outer membrane then allows entrance of FeEnt to the bacterial ]. FepB,C,D and G all participate in transport of the FeEnt through the inner membrane by means of an ].<ref>{{cite journal | author = Raymond, Kenneth N., Emily A. Dertz, and Sanggoo S. Kim | title = Bioinorganic Chemistry Special Feature: Enterobactin: an Archetype for Microbial Iron Transport | journal = ] | volume = 100 | year = 2003 | pages = 3584–3588 | doi = 10.1073/pnas.0630018100 | pmid = 12655062 | issue = 7 | pmc = 152965}}</ref> |
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] in bacterial cells triggers secretion of enterobactin into the extracellular environment, causing formation of a ] "]" wherein ferric ion is chelated to the conjugate base of enterobactin. In '']'', FepA in the bacterial outer membrane then allows entrance of FeEnt to the bacterial ]. FepB,C,D and G all participate in transport of the FeEnt through the inner membrane by means of an ].<ref name=Raymond2003 /> |
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Due to the extreme iron binding affinity of enterobactin, it is necessary to cleave FeEnt with ] to remove the iron. This degradation yields three 2,3-dihyroxybenzoyl-L-serine units. ] of the iron (Fe<sup>3+</sup> to Fe<sup>2+</sup>) occurs in conjunction with this cleavage, but no FeEnt bacterial ] enzyme has been identified, and the mechanism for this process is still unclear.<ref>{{cite journal | author = Ward, Thomas R., Andreas Lutz, Serge P. Parel, Jurgen Eusling, Philipp Gutlich, Peter Buglyo, and Chris Orvig | title = An Iron-Based Molecular Redox Switch as a Model for Iron Release From Enterobactin Via the Salicylate Binding Mode | journal = ] | volume = 38 | year = 1999 | pages = 5007–5017 | doi = 10.1021/ic990225e | pmid=11671244}}</ref> The reduction potential for Fe<sup>3+</sup>/Fe<sup>2+</sup>–enterobactin complex is pH dependent and varies from −0.57 V (vs ]) at pH 6 to −0.79 V at pH 7.4 to −0.99 at pH values higher than 10.4.<ref>{{cite journal |last1=Lee |first1=Chi Woo |last2=Ecker |first2=David J. |last3=Raymond |first3=Kenneth N. |year=1985 |title= |
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Due to the extreme iron binding affinity of enterobactin, it is necessary to cleave FeEnt with ] to remove the iron. This degradation yields three 2,3-dihydroxybenzoyl-L-serine units. ] of the iron (Fe<sup>3+</sup> to Fe<sup>2+</sup>) occurs in conjunction with this cleavage, but no FeEnt bacterial ] enzyme has been identified, and the mechanism for this process is still unclear.<ref name=Ward1999 /> The reduction potential for Fe<sup>3+</sup>/Fe<sup>2+</sup>–enterobactin complex is pH dependent and varies from −0.57 V (vs ]) at pH 6 to −0.79 V at pH 7.4 to −0.99 at pH values higher than 10.4.<ref name=Lee1985 /> |
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Coordination chemistry of microbial iron transport compounds. 34. The pH-dependent reduction of ferric enterobactin probed by electrochemical methods and its implications for microbial iron transport |journal=] |volume=107 |issue=24 |pages=6920–6923 |doi=10.1021/ja00310a030 }}</ref> |
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==History== |
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== History == |
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Enterochelin was discovered by the Gibson group, who named the siderophore "enterochelin." These initial studies established the structure and its relationship to 2,3-dihydroxybenzoic acid.<ref>{{cite journal | author = I. G. O'Brien, G. B. Cox, F. Gibson | title = Biologically active compounds containing 2,3-dihydroxybenzoic acid and serine formed by ''Escherichia coli'' | journal = ] | year = 1970 | volume = 201 | pages =453–60}}</ref> |
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Enterobactin was discovered by Gibson and Neilands groups in 1970.<ref name=Pollack1970 /><ref name="O'Brien1970" /> These initial studies established the structure and its relationship to 2,3-dihydroxybenzoic acid. |
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==References== |
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== References == |
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{{reflist}} |
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{{reflist|refs= |
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<ref name=Carrano1979>{{cite journal | last1 = Carrano | first1 = Carl J. | first2 = Kenneth N. | last2 = Raymond | name-list-style = vanc | title = Ferric Ion Sequestering Agents. 2. Kinetics and Mechanism of Iron Removal From Transferrin by Enterobactin and Synthetic Tricatechols | journal = ] | volume = 101 | year = 1979 | pages = 5401–5404 | doi = 10.1021/ja00512a047 | issue = 18}}</ref> |
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<ref name=Walsh1990>{{cite journal | last1 = Walsh | first1 = Christopher T. | first2 = Jun | last2 = Liu | first3 = Frank | last3 = Rusnak | first4 = Masahiro | last4 = Sakaitani | name-list-style = vanc | title = Molecular Studies on Enzymes in Chorismate Metabolism and the Enterobactin Biosynthetic Pathway | journal = ] | volume = 90 | year = 1990 | pages = 1105–1129 | doi = 10.1021/cr00105a003 | issue = 7}}</ref> |
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<ref name=Karpishin1992>{{cite journal | last1 = Karpishin | first1 = Timothy B. | last2 = Raymond | first2 = Kenneth N. | name-list-style = vanc | title = The First Structural Characterization of A Metal-Enterobactin Complex: 2- | journal = ] | volume = 31 | year = 1992 | pages = 466–468 | doi = 10.1002/anie.199204661 | issue = 4}}</ref> |
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<ref name=Raymond2003>{{cite journal | vauthors = Raymond KN, Dertz EA, Kim SS | title = Enterobactin: an archetype for microbial iron transport | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 100 | issue = 7 | pages = 3584–8 | date = April 2003 | pmid = 12655062 | pmc = 152965 | doi = 10.1073/pnas.0630018100 | doi-access = free }}</ref> |
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<ref name=Ward1999>{{cite journal | vauthors = Ward TR, Lutz A, Parel SP, Ensling J, Gütlich P, Buglyó P, Orvig C | title = An Iron-Based Molecular Redox Switch as a Model for Iron Release from Enterobactin via the Salicylate Binding Mode | journal = Inorganic Chemistry | volume = 38 | issue = 22 | pages = 5007–5017 | date = November 1999 | pmid = 11671244 | doi = 10.1021/ic990225e }}</ref> |
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<ref name=Lee1985>{{cite journal |last1=Lee |first1=Chi Woo |last2=Ecker |first2=David J. |last3=Raymond |first3=Kenneth N. | name-list-style = vanc |year=1985 |title=Coordination chemistry of microbial iron transport compounds. 34. The pH-dependent reduction of ferric enterobactin probed by electrochemical methods and its implications for microbial iron transport |journal=] |volume=107 |issue=24 |pages=6920–6923 |doi=10.1021/ja00310a030 }}</ref> |
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<ref name="O'Brien1970">{{cite journal | vauthors = O'Brien IG, Cox GB, Gibson F | title = Biologically active compounds containing 2,3-dihydroxybenzoic acid and serine formed by Escherichia coli | journal = Biochimica et Biophysica Acta (BBA) - General Subjects | volume = 201 | issue = 3 | pages = 453–60 | date = March 1970 | pmid = 4908639 | doi = 10.1016/0304-4165(70)90165-0 }}</ref> |
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<ref name=Pollack1970>{{cite journal | vauthors = Pollack JR, Neilands JB | title = Enterobactin, an iron transport compound from Salmonella typhimurium | journal = Biochemical and Biophysical Research Communications | volume = 38 | issue = 5 | pages = 989–92 | date = March 1970 | pmid = 4908541 | doi = 10.1016/0006-291X(70)90819-3 }}</ref> |
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