Elucidation of the Streptomyces coelicolor Pathway to 2-Undecylpyrrole, a Key Intermediate in Undecylprodiginine and Streptorubin B Biosynthesis
作者： SangJoon Mo , Paulina K. Sydor , Christophe Corre , Mamoun M. Alhamadsheh , Anna E. Stanley
DOI: 10.1016/J.CHEMBIOL.2007.11.015
关键词: Biosynthesis 、 Gene 、 Gene cluster 、 Biochemistry 、 Fatty acid 、 Undecylprodiginine 、 Stereochemistry 、 Streptorubin B 、 Mutant 、 Biology 、 Streptomyces coelicolor
摘要: The red gene cluster of Streptomyces coelicolor directs production undecylprodiginine. Here we report that this also streptorubin B and show 2-undecylpyrrole (UP) is an intermediate in the biosynthesis undecylprodiginine B. redPQRKL genes are involved UP biosynthesis. RedL RedK proposed to generate from dodecanoic acid or a derivative. A redK(-) mutant produces hydroxylated derivative, whereas redL(-) mutants require addition chemically synthesized for Fatty biosynthetic enzymes can provide acid, but efficient selective prodiginine requires RedPQR. Deletion redP, redQ, redR leads 80%-95% decrease array analogs with varying alkyl chains. In redR(-) mutant, ratio these be altered logical manner by feeding various fatty acids.
core.ac.uk
warwick.ac.uk
elsevier.com
sci-hub.se 参考文章(31)
Neil R. Williamson, Henrik T. Simonsen, Raef A. A. Ahmed, Gabrielle Goldet, Holly Slater, Louise Woodley, Finian J. Leeper, George P. C. Salmond, Biosynthesis of the red antibiotic, prodigiosin, in Serratia: identification of a novel 2-methyl-3-n-amyl-pyrrole (MAP) assembly pathway, definition of the terminal condensing enzyme, and implications for undecylprodigiosin biosynthesis in Streptomyces. Molecular Microbiology. ,vol. 56, pp. 971- 989 ,(2005) , 10.1111/J.1365-2958.2005.04602.X
Alessandra Mortellaro, Francesco Colotta, Simona Songia, Josée Golay, Chiara Fornasiero, Mario Ferrari, Anna Isetta, Paola Gnocchi, Roberto D’Alessio, New immunosuppressive drug PNU156804 blocks IL-2-dependent proliferation and NF-kappa B and AP-1 activation. Journal of Immunology. ,vol. 162, pp. 7102- 7109 ,(1999)
Tobias Kieser, Mervyn J Bibb, Mark J Buttner, Keith F Chater, David A Hopwood, Practical streptomyces genetics John Innes Foundation. ,(2000)
Esther Llagostera, Vanessa Soto-Cerrato, Ricky Joshi, Beatriz Montaner, Pepita Gimenez-Bonaf??, Ricardo P??rez-Tom??s, High cytotoxic sensitivity of the human small cell lung doxorubicin-resistant carcinoma (GLC4/ADR) cell line to prodigiosin through apoptosis activation. Anti-Cancer Drugs. ,vol. 16, pp. 393- 399 ,(2005) , 10.1097/00001813-200504000-00005
H. H. Wasserman, R. J. Sykes, P. Peverada, C. K. Shaw, R. J. Cushley, S. R. Lipsky, Biosynthesis of prodigiosin. Incorporation patterns of carbon-13-labeled alanine, proline, glycine, and serine elucidated by Fourier transform nuclear magnetic resonance Journal of the American Chemical Society. ,vol. 95, pp. 6874- 6875 ,(1973) , 10.1021/JA00801A080
Sylvie Garneau-Tsodikova, Pieter C. Dorrestein, Neil L. Kelleher, Christopher T. Walsh, Protein Assembly Line Components in Prodigiosin Biosynthesis: Characterization of PigA,G,H,I,J Journal of the American Chemical Society. ,vol. 128, pp. 12600- 12601 ,(2006) , 10.1021/JA063611L
Takayoshi Azuma, Naoko Watanabe, Hitoshi Yagisawa, Hajime Hirata, Michiko Iwamura, Yoshiro Kobayashi, Induction of apoptosis of activated murine splenic T cells by cycloprodigiosin hydrochloride, a novel immunosuppressant. Immunopharmacology. ,vol. 46, pp. 29- 37 ,(2000) , 10.1016/S0162-3109(99)00153-8
Mamoun M. Alhamadsheh, Nadaraj Palaniappan, Suparna DasChouduri, Kevin A. Reynolds, Modular polyketide synthases and cis double bond formation: establishment of activated cis-3-cyclohexylpropenoic acid as the diketide intermediate in phoslactomycin biosynthesis. Journal of the American Chemical Society. ,vol. 129, pp. 1910- 1911 ,(2007) , 10.1021/JA068818T
Peter P. Cherepanov, Wilfried Wackernagel, Gene disruption in Escherichia coli: TcR and KmR cassettes with the option of Flp-catalyzed excision of the antibiotic-resistance determinant. Gene. ,vol. 158, pp. 9- 14 ,(1995) , 10.1016/0378-1119(95)00193-A
Anna E. Stanley, Laura J. Walton, Malek Kourdi Zerikly, Christophe Corre, Gregory L. Challis, Elucidation of the Streptomyces coelicolor pathway to 4-methoxy-2,2'-bipyrrole-5-carboxaldehyde, an intermediate in prodiginine biosynthesis. Chemical Communications. pp. 3981- 3983 ,(2006) , 10.1039/B609556A