Isolation and structure determination of new siderophore albachelin from Amycolatopsis alba

BioMetals

Volumn 28, Issue 2, 2015, Pages 381-389

  Kodani, Shinya ^a   Komaki, Hisayuki ^b   Suzuki, Masahiro ^a   Hemmi, Hikaru ^c   Ohnishi Kameyama, Mayumi ^c  

^a SHIZUOKA UNIVERSITY   (Japan)

^b NATIONAL INSTITUTE OF TECHNOLOGY AND EVALUATION   (Japan)

^c NATIONAL FOOD RESEARCH INSTITUTE   (Japan)

Author keywords

Amycolatopsis alba; Biosynthesis; Peptide; Siderophore

Indexed keywords

BACTERIAL PROTEIN; GALLIUM; SIDEROPHORE;

ACTINOMYCETALES; BACTERIAL GENE; BIOSYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; GENETICS; ISOLATION AND PURIFICATION; METABOLISM; MULTIGENE FAMILY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TANDEM MASS SPECTROMETRY;

ACTINOMYCETALES; BACTERIAL PROTEINS; BIOSYNTHETIC PATHWAYS; GALLIUM; GENES, BACTERIAL; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; MULTIGENE FAMILY; SIDEROPHORES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY;

EID: 84939992112     PISSN: 09660844     EISSN: 15728773     Source Type: Journal    
DOI: 10.1007/s10534-015-9842-z     Document Type: Article

References (23)

1. Ahmed E, Holmstrom SJ (2014) Siderophores in environmental research: roles and applications. Microb Biotechnol 7:196-208. doi: 10.1111/1751-7915.12117
2. Bachmann BO, Ravel J (2009) Chapter 8. Methods for in silico prediction of microbial polyketide and nonribosomal peptide biosynthetic pathways from DNA sequence data. Methods Enzymol 458:181-217. doi: 10.1016/S0076-6879(09)04808-3
3. Barona-Gomez F, Wong U, Giannakopulos AE, Derrick PJ, Challis GL (2004) Identification of a cluster of genes that directs desferrioxamine biosynthesis in Streptomyces coelicolor M145. J Am Chem Soc 126:16282-16283. doi: 10.1021/ja045774k
4. Challis GL (2005) A widely distributed bacterial pathway for siderophore biosynthesis independent of nonribosomal peptide synthetases. Chembiochem Eur J Chem Biol 6:601-611. doi: 10.1002/cbic.200400283
5. Challis GL, Ravel J (2000) Coelichelin, a new peptide siderophore encoded by the Streptomyces coelicolor genome: structure prediction from the sequence of its non-ribosomal peptide synthetase. FEMS Microbiol Lett 187:111-114
6. Challis GL, Ravel J, Townsend CA (2000) Predictive, structure-based model of amino acid recognition by nonribosomal peptide synthetase adenylation domains. Chem Biol 7:211-224
7. Clardy J (2006) Stopping trouble before it starts. ACS Chem Biol 1:17-19. doi: 10.1021/cb0600029
8. Crosa JH, Walsh CT (2002) Genetics and assembly line enzymology of siderophore biosynthesis in bacteria. Microbiol Mol Biol Rev 66:223-249
9. Harada KI, Fujii K, Hayashi K, Suzuki M, Ikai Y, Oka H (1996) Application of D, L-FDLA derivatization to determination of absolute configuration of constituent amino acids in peptide by advanced Marfey's method. Tetrahedron Lett 37:3001-3004
10. Kodani S et al (2013a) Structure and biosynthesis of scabichelin, a novel tris-hydroxamate siderophore produced by the plant pathogen Streptomyces scabies 87.22. Org Biomol Chem 11:4686-4694. doi: 10.1039/c3ob40536b
11. Kodani S, Kobayakawa F, Hidaki M (2013b) Isolation and structure determination of new siderophore tsukubachelin B from Streptomyces sp. TM-74. Nat Prod Res 27:775-781. doi: 10.1080/14786419.2012.698412
12. Komaki H, Ichikawa N, Oguchi A, Hanamaki T, Fujita N (2012) Genome-wide survey of polyketide synthase and nonribosomal peptide synthetase gene clusters in Streptomyces turgidiscabies NBRC 16081. J Gen Appl Microbiol 58:363-372
13. Komaki H et al (2014) Genome based analysis of type-I polyketide synthase and nonribosomal peptide synthetase gene clusters in seven strains of five representative Nocardia species. BMC Genomics 15:323. doi: 10.1186/1471-2164-15-323
14. Lautru S, Deeth RJ, Bailey LM, Challis GL (2005) Discovery of a new peptide natural product by Streptomyces coelicolor genome mining. Nat Chem Biol 1:265-269. doi: 10.1038/nchembio731
15. Lazos O, Tosin M, Slusarczyk AL, Boakes S, Cortes J, Sidebottom PJ, Leadlay PF (2010) Biosynthesis of the putative siderophore erythrochelin requires unprecedented crosstalk between separate nonribosomal peptide gene clusters. Chem Biol 17:160-173. doi: 10.1016/j.chembiol.2010.01.011
16. Mercier A, Labbe S (2010) Iron-dependent remodeling of fungal metabolic pathways associated with ferrichrome biosynthesis. Appl Environ Microbiol 76:3806-3817. doi: 10.1128/AEM.00659-10
17. Ochi K, Hosaka T (2013) New strategies for drug discovery: activation of silent or weakly expressed microbial gene clusters. Appl Microbiol Biotechnol 97:87-98. doi: 10.1007/s00253-012-4551-9
18. Park HM et al (2013) Genome-based cryptic gene discovery and functional identification of NRPS siderophore peptide in Streptomyces peucetius. Appl Microbiol Biotechnol 97:1213-1222. doi: 10.1007/s00253-012-4268-9
19. Robbel L, Knappe TA, Linne U, Xie X, Marahiel MA (2010) Erythrochelin -A hydroxamate-type siderophore predicted from the genome of Saccharopolyspora erythraea. FEBS J 277:663-676. doi: 10.1111/j.1742-4658.2009.07512.x
20. Rottig M, Medema MH, Blin K, Weber T, Rausch C, Kohlbacher O (2011) NRPSpredictor2 -A web server for predicting NRPS adenylation domain specificity. Nucleic Acids Res 39:W362-W367. doi: 10.1093/nar/gkr323
21. Seyedsayamdost MR, Traxler MF, Zheng SL, Kolter R, Clardy J (2011) Structure and biosynthesis of amychelin, an unusual mixed-ligand siderophore from Amycolatopsis sp. AA4. J Am Chem Soc 133:11434-11437. doi: 10.1021/ja203577e
22. Sieber SA, Marahiel MA (2005) Molecular mechanisms underlying nonribosomal peptide synthesis: approaches to new antibiotics. Chem Rev 105:715-738. doi: 10.1021/cr0301191
23. Zerikly M, Challis GL (2009) Strategies for the discovery of new natural products by genome mining. Chembiochem Eur J Chem Biol 10:625-633. doi: 10.1002/cbic.200800389