Incorporation of Nonproteinogenic Amino Acids in Class I and II Lantibiotics

被引：30

作者：

Kakkar, Nidhi ^{[1
,2
]}

Perez, Jessica G. ^{[4
]}

Liu, Wenshe R. ^{[3
]}

Jewett, Michael C. ^{[4
]}

van der Donk, Wilfred A. ^{[1
,2
]}

机构：

[1] Univ Illinois, Howard Hughes Med Inst, Dept Chem, 600 South Mathews Ave, Urbana, IL 61801 USA

[2] Univ Illinois, Roger Adams Lab, Dept Chem, 600 South Mathews Ave, Urbana, IL 61801 USA

[3] Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA

[4] Northwestern Univ, Dept Chem & Biol Engn, Evanston, IL 60208 USA

来源：

ACS CHEMICAL BIOLOGY | 2018年 / 13卷 / 04期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

TRANSFER-RNA SYNTHETASE; SUBSTITUTED PHENYLALANINE DERIVATIVES; PRECURSOR LIPID II; ESCHERICHIA-COLI; DEGRADATION-PRODUCTS; NATURAL-PRODUCTS; GENETIC-CODE; NUKACIN ISK-1; LACTICIN; 481; NISIN;

D O I：

10.1021/acschembio.7b01024

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：

Lantibiotics are ribosomally synthesized and post-translationally modified peptide natural products that contain thioether cross-links formed by lanthionine and methyllanthionine residues. They exert potent antimicrobial activity against Gram-positive bacteria. We herein report production of analogues of two lantibiotics, lacticin 481 and nisin, that contain nonproteinogenic amino acids using two different strategies involving amber stop codon suppression technology. These methods complement recent alternative approaches to incorporate nonproteinogenic amino acids into lantibiotics.

引用

页码：951 / 957

页数：7

共 70 条

[1] Evolution of translation machinery in recoded bacteria enables multi-site incorporation of nonstandard amino acids [J].

Amiram, Miriam ;

Haimovich, Adrian D. ;

Fan, Chenguang ;

Wang, Yane-Shih ;

Aerni, Hans-Rudolf ;

Ntai, Ioanna ;

Moonan, Daniel W. ;

Ma, Natalie J. ;

Rovner, Alexis J. ;

Hong, Seok Hoon ;

Kelleher, Neil L. ;

Goodman, Andrew L. ;

Jewett, Michael C. ;

Soell, Dieter ;

Rinehart, Jesse ;

Isaacs, Farren J. .

NATURE BIOTECHNOLOGY, 2015, 33 (12) :1272-+

[2] 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

[3] Recombinant protein expression in Escherichia coli [J].

Baneyx, F .

CURRENT OPINION IN BIOTECHNOLOGY, 1999, 10 (05) :411-421

[4] Facile Removal of Leader Peptides from Lanthipeptides by Incorporation of a Hydroxy Acid [J].

Bindman, Noah A. ;

Bobeica, Silvia C. ;

Liu, Wenshe R. ;

van der Donk, Wilfred A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (22) :6975-6978

[5] Generation of an actagardine A variant library through saturation mutagenesis [J].

Boakes, Steven ;

Ayala, Tania ;

Herman, Mark ;

Appleyard, Antony N. ;

Dawson, Michael J. ;

Cortes, Jesus .

APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 2012, 95 (06) :1509-1517

[6] Use of the cell wall precursor lipid II by a pore-forming peptide antibiotic [J].

Breukink, E ;

Wiedemann, I ;

van Kraaij, C ;

Kuipers, OP ;

Sahl, HG ;

de Kruijff, B .

SCIENCE, 1999, 286 (5448) :2361-2364

[7] Role of lipid-bound peptidoglycan precursors in the formation of pores by nisin, epidermin and other lantibiotics [J].

Brötz, H ;

Josten, M ;

Wiedemann, I ;

Schneider, U ;

Götz, F ;

Bierbaum, G ;

Sahl, HG .

MOLECULAR MICROBIOLOGY, 1998, 30 (02) :317-327

[8] The lantibiotic mersacidin inhibits peptidoglycan synthesis by targeting lipid II [J].

Brötz, H ;

Bierbaum, G ;

Leopold, K ;

Reynolds, PE ;

Sahl, HG .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1998, 42 (01) :154-160

[9] ISOLATION AND CHARACTERIZATION OF 2 DEGRADATION PRODUCTS DERIVED FROM THE PEPTIDE ANTIBIOTIC NISIN [J].

CHAN, WC ;

BYCROFT, BW ;

LIAN, LY ;

ROBERTS, GCK .

FEBS LETTERS, 1989, 252 (1-2) :29-36

[10] Lacticin 481 synthetase phosphorylates its substrate during lantibiotic production [J].

Chatterjee, C ;

Miller, LM ;

Leung, YL ;

Xie, LL ;

Yi, MS ;

Kelleher, NL ;

van der Donk, WA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (44) :15332-15333

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