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
[1]   Synthetic studies towards bottromycin [J].
Ackermann, Stefanie ;
Lerchen, Hans-Georg ;
Haebich, Dieter ;
Ullrich, Angelika ;
Kazmaier, Uli .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 :1652-1656
[2]   Characterization of the Stereoselective P450 Enzyme BotCYP Enables the In Vitro Biosynthesis of the Bottromycin Core Scaffold [J].
Adam, Sebastian ;
Franz, Laura ;
Milhim, Mohammed ;
Bernhardt, Rita ;
Kalinina, Olga, V ;
Koehnke, Jesko .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (49) :20560-20565
[3]   An efficient and stereodivergent synthesis of threo- and erythro-β-methylphenylalanine.: Resolution of each racemic pair by semipreparative HPLC [J].
Alías, M ;
López, MP ;
Cativiela, C .
TETRAHEDRON, 2004, 60 (04) :885-891
[4]  
[Anonymous], [No title captured], Patent No. [WO 2006/103010, 2006103010]
[5]   Ribosomally synthesized and post-translationally modified peptide natural products: overview and recommendations for a universal nomenclature [J].
Arnison, Paul G. ;
Bibb, Mervyn J. ;
Bierbaum, Gabriele ;
Bowers, Albert A. ;
Bugni, Tim S. ;
Bulaj, Grzegorz ;
Camarero, Julio A. ;
Campopiano, Dominic J. ;
Challis, Gregory L. ;
Clardy, Jon ;
Cotter, Paul D. ;
Craik, David J. ;
Dawson, Michael ;
Dittmann, Elke ;
Donadio, Stefano ;
Dorrestein, Pieter C. ;
Entian, Karl-Dieter ;
Fischbach, Michael A. ;
Garavelli, John S. ;
Goeransson, Ulf ;
Gruber, Christian W. ;
Haft, Daniel H. ;
Hemscheidt, Thomas K. ;
Hertweck, Christian ;
Hill, Colin ;
Horswill, Alexander R. ;
Jaspars, Marcel ;
Kelly, Wendy L. ;
Klinman, Judith P. ;
Kuipers, Oscar P. ;
Link, A. James ;
Liu, Wen ;
Marahiel, Mohamed A. ;
Mitchell, Douglas A. ;
Moll, Gert N. ;
Moore, Bradley S. ;
Mueller, Rolf ;
Nair, Satish K. ;
Nes, Ingolf F. ;
Norris, Gillian E. ;
Olivera, Baldomero M. ;
Onaka, Hiroyasu ;
Patchett, Mark L. ;
Piel, Joern ;
Reaney, Martin J. T. ;
Rebuffat, Sylvie ;
Ross, R. Paul ;
Sahl, Hans-Georg ;
Schmidt, Eric W. ;
Selsted, Michael E. .
NATURAL PRODUCT REPORTS, 2013, 30 (01) :108-160
[6]   Isolation and structure determination of two new nosiheptide-type compounds provide insights into the function of the cytochrome P450 oxygenase NocV in nocathiacin biosynthesis [J].
Bai, Xuebing ;
Guo, Heng ;
Chen, Dandan ;
Yang, Qian ;
Tao, Jiang ;
Liu, Wen .
ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (03) :584-589
[7]   Hydroxyalkyl Thiazolines, a New Class of Highly Efficient Ligands for Carbonyl Additions [J].
Bauer, Michael ;
Maurer, Erattke ;
Hoffmann, Svenja M. ;
Kazmaier, Uli .
SYNLETT, 2008, (20) :3203-3207
[8]  
Benjdia A, 2017, NAT CHEM, V9, P698, DOI [10.1038/NCHEM.2714, 10.1038/nchem.2714]
[9]   PLASMID CLONING VECTORS FOR THE CONJUGAL TRANSFER OF DNA FROM ESCHERICHIA-COLI TO STREPTOMYCES SPP [J].
BIERMAN, M ;
LOGAN, R ;
OBRIEN, K ;
SENO, ET ;
RAO, RN ;
SCHONER, BE .
GENE, 1992, 116 (01) :43-49
[10]   One-Carbon Ring Expansion of Azetidines via Ammonium Ylide [1,2]-Shifts: A Simple Route to Substituted Pyrrolidines [J].
Bott, Tina M. ;
Vanecko, John A. ;
West, F. G. .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (07) :2832-2836