Bottromycins-biosynthesis, synthesis and activity

被引:42
作者
Franz, Laura [1 ]
Kazmaier, Uli [2 ]
Truman, Andrew W. [3 ]
Koehnke, Jesko [1 ,4 ]
机构
[1] Helmholtz Ctr Infect Res HZI, Helmholtz Inst Pharmaceut Res Saarland HIPS, Saarland Univ Campus, D-66123 Saarbrucken, Germany
[2] Saarland Univ, Organ Chem, Campus Geb C4 2, D-66123 Saarbrucken, Germany
[3] John Innes Ctr, Dept Mol Microbiol, Norwich, Norfolk, England
[4] Univ Glasgow, Sch Chem, Glasgow, Lanark, Scotland
基金
英国生物技术与生命科学研究理事会;
关键词
D O I
10.1039/d0np00097c
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Covering: 1950s up to the end of 2020 Bottromycins are a class of macrocyclic peptide natural products that are produced by several Streptomyces species and possess promising antibacterial activity against clinically relevant multidrug-resistant pathogens. They belong to the ribosomally synthesised and post-translationally modified peptide (RiPP) superfamily of natural products. The structure contains a unique four-amino acid macrocycle formed via a rare amidine linkage, C-methylation and a d-amino acid. This review covers all aspects of bottromycin research with a focus on recent years (2009-2020), in which major advances in total synthesis and understanding of bottromycin biosynthesis were achieved.
引用
收藏
页码:1659 / 1683
页数:25
相关论文
共 136 条
[21]   Rapid and Robust Yeast-Mediated Pathway Refactoring Generates Multiple New Bottromycin-Related Metabolites [J].
Eyles, Tom H. ;
Vior, Natalia M. ;
Truman, Andrew W. .
ACS SYNTHETIC BIOLOGY, 2018, 7 (05) :1211-1218
[22]   An efficient method for the stereoselective synthesis of cis-3-substituted prolines:: conformationally constrained α-amino acids [J].
Flamant-Robin, C ;
Wang, Q ;
Chiaroni, A ;
Sasaki, NA .
TETRAHEDRON, 2002, 58 (52) :10475-10484
[23]   Macroamidine Formation in Bottromycins Is Catalyzed by a Divergent YcaO Enzyme [J].
Franz, Laura ;
Adam, Sebastian ;
Santos-Aberturas, Javier ;
Truman, Andrew W. ;
Koehnke, Jesko .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (50) :18158-18161
[24]   Metagenome Mining Reveals Polytheonamides as Posttranslationally Modified Ribosomal Peptides [J].
Freeman, Michael F. ;
Gurgui, Cristian ;
Helf, Maximilian J. ;
Morinaka, Brandon I. ;
Uria, Agustinus R. ;
Oldham, Neil J. ;
Sahl, Hans-Georg ;
Matsunaga, Shigeki ;
Piel, Joern .
SCIENCE, 2012, 338 (6105) :387-390
[25]   The proteomics of N-terminal methionine cleavage [J].
Frottin, Frederic ;
Martinez, Aude ;
Peynot, Philippe ;
Mitra, Sanghamitra ;
Holz, Richard C. ;
Giglione, Carmela ;
Meinnel, Thierry .
MOLECULAR & CELLULAR PROTEOMICS, 2006, 5 (12) :2336-2349
[26]   Total Synthesis and Stereochemistry Revision of Mannopeptimycin Aglycone [J].
Fuse, Shinichiro ;
Koinuma, Hirotsugu ;
Kimbara, Atsushi ;
Izumikawa, Miho ;
Mifune, Yuto ;
He, Haiyin ;
Shin-ya, Kazuo ;
Takahashi, Takashi ;
Doi, Takayuki .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (34) :12011-12017
[27]   Posttranslational β-methylation and macrolactamidination in the biosynthesis of the bottromycin complex of ribosomal peptide antibiotics [J].
Gomez-Escribano, Juan Pablo ;
Song, Lijiang ;
Bibb, Mervyn J. ;
Challis, Gregory L. .
CHEMICAL SCIENCE, 2012, 3 (12) :3522-3525
[28]   Engineering Streptomyces coelicolor for heterologous expression of secondary metabolite gene clusters [J].
Gomez-Escribano, Juan Pablo ;
Bibb, Mervyn J. .
MICROBIAL BIOTECHNOLOGY, 2011, 4 (02) :207-215
[29]   In Vitro Biosynthesis of Peptides Containing Exotic Azoline Analogues [J].
Goto, Yuki ;
Suga, Hiroaki .
CHEMBIOCHEM, 2020, 21 (1-2) :84-87
[30]   Three-Dimensional Solution Structure of Bottromycin A2: A Potent Antibiotic Active against Methicillin-Resistant Staphylococcus aureus and Vancomycin-Resistant Enterococci [J].
Gouda, Hiroaki ;
Kobayashi, Yutaka ;
Yamada, Takeshi ;
Ideguchi, Tetsuya ;
Sugawara, Akihiro ;
Hirose, Tomoyasu ;
Omura, Satoshi ;
Sunazuka, Toshiaki ;
Hirono, Shuichi .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2012, 60 (02) :169-171