title: Amino acid variability in the peptide composition of a suite of amphiphilic peptide siderophores from an open ocean Vibrio species.
abstract: In response to iron-depleted aerobic conditions, bacteria often secrete low molecular weight, high-affinity iron(III)-complexing ligands, siderophores, to solubilize and sequester iron(III). Many marine siderophores are amphiphilic and are produced in suites, wherein each member within a particular suite has the same iron(III)-binding polar head group which is appended by one or two fatty acids of differing length, degree of unsaturation, and degree of hydroxylation, establishing the suite composition. We report the isolation and structural characterization of a suite of siderophores from marine bacterial isolate Vibrio sp. Nt1. On the basis of structural analysis, this suite of siderophores, the moanachelins, is amphiphilic and composed of two N-acetyl-N-hydroxy-D-ornithines, one N-acetyl-N-hydroxy-L-ornithine, and either a glycine or an L-alanine, appended with various saturated and unsaturated fatty acid tails. The variation in the small side-chain amino acid is the first occurrence of variation in the peptidic head group structure of a set of siderophores produced by a single bacterium.
authors.affiliation: Graduate Program in Marine Science, University of California, Santa Barbara, CA 93106, USA.
authors.forename: Julia M
authors.initials: JM
authors.lastname: Gauglitz
authors.forename: Alison
authors.initials: A
authors.lastname: Butler
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry*; D017262:Siderophores / Q000737:chemistry*; D013501:Surface-Active Agents / Q000737:chemistry*; D014733:Vibrio / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D010455:Peptides; D017262:Siderophores; D013501:Surface-Active Agents
references.citation: Org Lett. 2011 Apr 1;13(7):1758-61
references.pmid: 21384820
references.citation: Biochem J. 1969 Dec;115(5):1031-50
references.pmid: 5360674
references.citation: Biochemistry. 2000 Dec 19;39(50):15522-30
references.pmid: 11112538
references.citation: Biomed Mass Spectrom. 1984 Nov;11(11):601
references.pmid: 6525415
references.citation: J Biol Inorg Chem. 2006 Jul;11(5):633-41
references.pmid: 16791646
references.citation: Biochemistry. 2002 Jul 30;41(30):9718-26
references.pmid: 12135394
references.citation: Chem Biol. 2000 Mar;7(3):211-24
references.pmid: 10712928
references.citation: Methods Enzymol. 2009;458:337-51
references.pmid: 19374989
references.citation: Science. 2000 Feb 18;287(5456):1245-7
references.pmid: 10678827
references.citation: Nat Prod Rep. 2000 Feb;17(1):99-116
references.pmid: 10714901
references.citation: Chem Biol. 1999 Jun;6(6):385-400
references.pmid: 10375542
references.citation: Biometals. 2003 Jun;16(2):263-70
references.pmid: 12572684
references.citation: Biometals. 2011 Feb;24(1):85-92
references.pmid: 20853137
references.citation: Proc Natl Acad Sci U S A. 2003 Apr 1;100(7):3754-9
references.pmid: 12651947
references.citation: Biochemistry. 1989 Aug 22;28(17):6827-35
references.pmid: 2531000
references.citation: J Inorg Biochem. 2012 Feb;107(1):90-5
references.pmid: 22178670
references.citation: Biochemistry. 1998 Feb 24;37(8):2648-59
references.pmid: 9485415
references.citation: Nucleic Acids Res. 2005 Oct 12;33(18):5799-808
references.pmid: 16221976
references.citation: Biometals. 2010 Feb;23(1):129-34
references.pmid: 19816776
references.citation: Tuberculosis (Edinb). 2004;84(1-2):110-30
references.pmid: 14670352
references.citation: Chem Biol. 1999 Aug;6(8):493-505
references.pmid: 10421756
references.citation: Anal Biochem. 1987 Jan;160(1):47-56
references.pmid: 2952030
references.citation: Org Lett. 2011 Oct 7;13(19):5144-7
references.pmid: 21888371
references.citation: Chem Biol. 1998 Nov;5(11):631-45
references.pmid: 9831524
references.citation: J Bacteriol. 1999 Aug;181(15):4443-51
references.pmid: 10419938
references.citation: Chem Rev. 2005 Feb;105(2):715-38
references.pmid: 15700962
references.citation: Environ Microbiol. 2012 Jan;14(1):114-28
references.pmid: 21883791
references.citation: Environ Microbiol. 2013 Mar;15(3):916-27
references.pmid: 23320867
references.citation: Environ Microbiol. 2013 Jun;15(6):1661-73
references.pmid: 23126435
references.citation: Biochemistry. 2000 Mar 7;39(9):2297-306
references.pmid: 10694396
references.citation: J Nat Prod. 2009 May 22;72(5):884-8
references.pmid: 19320498
references.citation: Biochemistry. 1999 Nov 9;38(45):14941-54
references.pmid: 10555976