90:
177:
InChI=1S/C41H61N9O20/c1-22(16-34(57)58)13-31(54)48(68)10-4-7-25-38(64)44-26(8-5-11-49(69)32(55)14-23(2)17-35(59)60)39(65)45-27(9-6-12-50(70)33(56)15-24(3)18-36(61)62)40(66)47-29(21-52)41(67)46-28(20-51)37(63)42-19-30(53)43-25/h13-15,25-29,51-52,68-70H,4-12,16-21H2,1-3H3,(H,42,63)(H,43,53)(H,44,64)(H,45,65)(H,46,67)(H,47,66)(H,57,58)(H,59,60)(H,61,62)/b22-13+,23-14+,24-15+/t25-,26-,27-,28-,29-/m0/s1
24:
355:
349:(Fer4). Methyl glutaconyl-CoA is then coupled with hydroxy ornithine (derived from the ornithine monoxygenase, Sid1, of the precursor ornithine) via hydroxyornithine acylase (Fer5) to yield methylglutaconyl hydroxy ornithine. Cyclization of three methylglutaconyl hydroxy ornithine with a glycine and two serine amino acids via NRPS Fer3 yields ferrichrome A.
306:
in 1952, the ferrichrome family of siderophores contains at least 20 structurally distinct members of cyclic hexapeptides that chelate ferric iron via an octahedral coordination geometry through the oxygen atoms of the hydroxyl and the acyl groups of the three ornithine residues. Ferrichrome A was
571:
Hesseltine, C. W.; Pidacks, C.; Whitehill, A. R.; Bohonos, N.; Hutchings, B. L.; Williams, J. H. (March 1952). "Coprogen, A New Growth Factor for
Coprophilic Fungi".
44:)-5--hydroxyamino]propyl]-11,14-bis(hydroxymethyl)-3,6,9,12,15,18-hexaoxo-1,4,7,10,13,16-hexazacyclooctadec-2-yl]propyl-hydroxyamino]-3-methyl-5-oxopent-3-enoic acid
657:
Winterberg, Britta; Uhlmann, Stefanie; Linne, Uwe; Lessing, Franziska; Marahiel, Mohamed A.; Eichhorn, Heiko; Kahmann, Regine; Schirawski, Jan (February 21, 2010).
193:
201:
C/C(=C\C(=O)N(CCC1C(=O)N(C(=O)N(C(=O)N(C(=O)N(C(=O)NCC(=O)N1)CO)CO)CCCN(C(=O)/C=C(\C)/CC(=O)O)O)CCCN(C(=O)/C=C(\C)/CC(=O)O)O)O)/CC(=O)O
342:
168:
271:
122:
536:
Neilands, J. B. (October 1952). "A Crystalline Organo-iron
Pigment from a Rust Fungus (Ustilago sphaerogena)1".
721:
716:
36:
346:
56:
639:
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Winkelmann, Günther (2007-01-18). "Ecology of siderophores with special reference to the fungi".
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302:, to aid in the sequestration and increase bioavailability of iron. Since the discovery of
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345:(HMG-CoA). The next step involves the conversion of HMG-CoA to methyl glutaconyl-CoA via
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382:
265:
154:
710:
679:
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333:, the ferrichrome A biosynthetic pathway begins with the HMG-CoA synthase (Hcs1) of
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found as one of the two siderophores produced by the biotrophic basidiomycete
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432:"Siderophores: Structure and Function of Microbial Iron Transport Compounds"
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298:. Microorganisms produce and secrete potent iron chelators, also known as
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family. Iron is an essential element for the survival and proliferation of
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381:
Abbaspour, Nazanin; Hurrell, Richard; Kelishadi, Roya (February 2014).
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Except where otherwise noted, data are given for materials in their
659:"Elucidation of the complete ferrichrome A biosynthetic pathway in
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89:
79:
481:"Siderophore-Based Iron Acquisition and Pathogen Control"
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Miethke, Marcus; Marahiel, Mohamed A. (2007-09-01).
383:"Review on iron and its importance for human health"
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485:Microbiology and Molecular Biology Reviews
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573:Journal of the American Chemical Society
538:Journal of the American Chemical Society
387:Journal of Research in Medical Sciences
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313:during its saprotrophic growth phase.
180:Key: DKSPATNIHZSGOP-NJIQAGLESA-N
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358:Biosynthesis of ferrichrome A in
680:10.1111/j.1365-2958.2010.07048.x
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436:Journal of Biological Chemistry
268:(at 25 °C , 100 kPa).
430:Neilands, J. B. (1995-11-10).
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1:
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343:hydroxymethyl glutaryl-CoA
317:is the causative agent of
620:10.1007/s10534-006-9076-1
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449:10.1074/jbc.270.45.26723
667:Molecular Microbiology
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497:10.1128/MMBR.00012-07
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585:10.1021/ja01125a525
550:10.1021/ja01139a033
442:(45): 26723–26726.
347:enoyl-CoA hydratase
258: g·mol
18:
363:
341:for generation of
272:Infobox references
114: Iron complex
16:
544:(19): 4846–4847.
280:Chemical compound
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91:Interactive image
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339:acetoacetyl-CoA
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17:Ferrichrome A
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50:Identifiers
41:
579:(5): 1362.
304:ferrichrome
292:ferrichrome
288:siderophore
210:Properties
711:Categories
368:References
335:acetyl-CoA
251:Molar mass
102:ChemSpider
78:3D model (
67:15258-80-7
57:CAS Number
37:IUPAC name
689:0950-382X
628:0966-0844
608:BioMetals
593:0002-7863
558:0002-7863
505:1092-2172
458:0021-9258
399:1735-1995
331:U. maydis
319:corn smut
315:U. maydis
296:organisms
155:101031659
132:239-301-9
124:EC Number
697:20070524
644:25877869
636:17235665
523:17804665
417:24778671
514:2168645
466:7592901
408:3999603
290:in the
256:999.982
142:PubChem
111:4952558
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194:SMILES
31:Names
640:S2CID
286:is a
169:InChI
80:JSmol
693:PMID
685:ISSN
632:PMID
624:ISSN
589:ISSN
554:ISSN
519:PMID
501:ISSN
462:PMID
454:ISSN
413:PMID
395:ISSN
337:and
675:doi
616:doi
581:doi
546:doi
509:PMC
493:doi
444:doi
440:270
403:PMC
329:In
145:CID
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241:O
238:9
235:N
229:H
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42:E
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Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
