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Nisin and Novel Lantibiotics

Proceedings of theFirst International Workshop on LantibioticsApril 15-18, 1991Physikzentrum Bad Honnef, F. R. G.

Edited byGiinther JungInstitut fur Organische ChemieUniversitat TubingenAuf der Morgenstelle 18D-7400 TubingenGermanyandHans-Georg SahlInstitut fur Medizinische MikrobiologieUniversitat BonnSigmund-Freud-Str. 25D-5300 BonnGermany

ESCOM Leiden 1991


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ContentsPreface v

Contents ix

Abbreviations xiiiIntroductionLantibiotics: a survey 1Gunther Jung

1. Conformation of lantibiotics1.1. The spatial structure of nisin in aqueous solution 35

Frank J. M. van de Ven, Henno W. van den Hooven, Ruud N. H. Konings andCornelis W. Hilbers

1.2. NMRstudies of the solution structure of nisin A and related peptides 43Lu-Yun Lian, Weng C. Chan, S. David Morley, Gordon C. K. Roberts, BarrieW. Bycroft and David Jackson

1.3. Conformations of nisin and its fragments using synthesis, NMR and computer 59simulationsMurray Goodman, Darryl E. Palmer, Dale Mierke, Seonggu Ro, KenichiNunami, Tateaki Wakamiya, Koichi Fukase, Shingo Horimoto, Manabu Ki-tazawa, Hiroshi Fujita, Akira Kubo and Tetsuo Shiba

1.4. Structure of cinnamycin (Ro 09-0198) in solution 76Horst Kessler, Stephan Seip, Thomas Wein, Stefan Steuernagel and Martin Will

1.5. The three-dimensional solution structure of gaUidermin determined by NMR- 91based molecular graphicsStefan Freund, Gunther Jung, Oliver Gutbrod, Gerd Folkers and William A.Gibbons

1.6. NMR and circular dichroism studies on Pep5 103Stefan Freund, Gunther Jung, William A. Gibbons and Hans-Georg Sahl

2. Structure elucidation of lantibiotics2.1. Structure of the lanthionine peptides nisin, ancovenin and lanthiopeptin 113

Tetsuo Shiba, Tateaki Wakamiya, Koichi Fukase, Yasuyuki Ueki, TadashiTeshima and Masahiro Nishikawa

2.2. NMR and activity studies of nisin degradation products 123Harry S. Rollema, Paula Both andRoland J. Siezen


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Contents2.3. Duramycin B and C, two new lanthionine-containing antibiotics as inhibitors of 131phospholipase A2, and structu ral revision of duramycin and cinnamycin

Andreas Fredenhagen, Fritz Mdrki, Gabriele Fendrich, Walter Marki, JohannesGruner, Jan van Oostrum, Fritz Raschdorf and Heinrich H. Peter2.4. Stru cture elucidation of the tricyclic lantibiotic Pep5 containing eight positively 141charged amino acidsRoland Kellner, Gunther Jung and Hans-Georg Sahl

2.5. NM R-spectroscopic investigations on mersacidin 159Herbert Kogler, Markus Bauch, Hans- Wolfram Fehlhaber, Christian Griesinger,Wolfgang Schubert and Volker Teetz

2.6. Isolation and part ial structure of streptococcin A-FF22 171Ralph W . Jack and John R. Tagg

2.7. Frequency of lantibiotic production among coagulase-negative staphylococci: re- 180isolation of epiderminAngelika Prey, Roland Kellner, G unther Jung and Hans-Georg Sahl

3 . Chemical synthesis of lantibiotics and prelantibiotics3.1. Studies on chemical synthesis of the lanthionine peptid e nisin 189Tateaki Wakamiya, Koichi Fukase, Akihiko Sano, Kuniaki Shimbo, Manabu Ki-tazawa, Shingo H orimoto, Hiroshi Fujita, Akira Ku bo, Yasushi Mae shiro andTetsuo Shiba3.2. Synthesis and charac terization of pro- and prepeptides related to nisin and sub- 204tilinBarrie W. Bycroft, Weng C. Chan and Gordon C. K. Roberts3.3. Synthesis and con formational analysis of lantibiotic leader-, pro- and pre- 218peptides

Annette G. Beck-Sickinger and Gunther Jung4 . Genetic analysis of nisin production4.1. Physical and genetic analysis of the ckromosomally located transposon Tn5301, 23 1responsible for nisin biosynthesis

Helen M. Dodd, Nikki Horn, Simon Swindell and Michael J. Gasson4.2. Molecular analysis and evolution of conjugative transpo sons encoding nisin pro- 243duction and sucrose fermentation in Lactococcus lactisPeter J. G. Rauch, Marke M. Beerthuyzen and Willem M. de Vos4.3. Expression of wild-type and mutant nisin genes in Lactococcus lactis 250

Oscar P. Kuipers, Wyanda M. G. J. Yap, Harry S. Rollema, Marke M .Beerthuyzen, Roland J. Siezen and Willem M. de Vos

4.4. A na tura l nisin variant 260Tytti Graeffe, Helena Rintala, Lars Paulin and Per Saris


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Contents5. Gen es involved in biosy nthes is of lantibiotics5.1. The operon-like organisation of lantibiotic epidermin biosynthesis genes 269

Norbe rt Schnell, Germ ar Eng elke, Johann es Augu stin, R alf Rosen stein,Friedrich Gotz and Karl-Dieter Entian

5.2. Identification of epidermin biosynthetic genes by complem entation studies and 277heterologous expressionJohannes Augustin, Ralf Rosenstein, Thomas Kupke, Uschi Schneider, NorbertSchnell, Germar Engelke, Karl-Dieter Entian and Friedrich Gotz

5.3. Biosynthesis and mechanism of action of nisin and subtilin 287J. Norm an Hansen, Yong Joon C hung, Wei Liu and Mark T. Steen

5.4. Isolation and characteriza tion of the cinnamycin stru ctur al gene 303Karl-Dieter Entian and Cortina Kaletta

5.5. An operon-like struc ture of genes involved in subtilin biosynthesis 309Cortina Kaletta, Cora Klein, Norb ert Schnell and Karl-Dieter E ntian

5.6. Genetic analysis of the producer self-protection mechanism ("imm unity") again st 320Pep5Michaela Reis and Hans-Georg Sahl6. Biosy nthet ic precursors6.1. Isolation of Pep 5 prep eptid es in different stages of modification 332

Hans-Georg Sahl, M ichaela Reis, M onika Eschb ach, Christiane Szekat, Ann etteG. Beck-Sickinger, Jorg Metzger, Stefan Stevanovic and Gunther Jung

7. M ode of action of lantibiotics7.1. Pore formation in bacte rial membranes by cationic lantibiotics 347

Hans-Georg Sahl7.2. Mechanism of channel-formation by lantibiotics in black lipid mem branes 359

Roland Benz, G unther Jung and Hans-Georg Sahl7.3. The mechanism of action of the lantibiotic nisin in artificial membranes 373Tjakko Abee, Fu H. Gao and Wil N. Konings7.4. Induc tion of autolysis of Staphylococcus simvlans 22 by Pep5 and nisin and 386

influence of the cationic peptides on the activity of the autolytic enzymesGabriele Bierbaum and Hans-Georg Sahl

8. Ferm entation and purification of lantibiotics8.1. Microbial ma nipulatio n of nisin biosynthesis and fermentation 397

Luc De Vuyst and Erick J. Vandamme8.2. Op timization of fermentation and purification of gallidermin and epidermin 410

Volker Ungermann, Klaus Goeke, Hans-Peter Fiedler and Hans Zdhner8.3. Stra tegy for purification of lantib iotics 422

Hermann Allgaier, Joachim W alter, Michael Schluter and Rolf-Gunther Werner

XI


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Contents9. Ap plications of lantibiotics9.1. Applications of nisin: a litera ture survey 434

Ernst M olitor and Hans-Georg Sahl9.2. App lication of nisin A and nisin Z in dairy technology 440

Jeroen Hugenholtz and Gerrie J. C . M. de Veer9.3. Chemotherapeutic properties of mersacidin in vitro and in vivo 448Micha el Limbert, Dieter Isert, Norb ert Klesel, Astrid Ma rkus, Gerhard Seibert,Sukumar Chatterjee, Dipak K. Chatterjee, Rajendra H. Jani and Binmal N.Ganguli

AppendixApp endix: definitions and nomenclature of lantibiotics 457Willem M. de Vos, Gunther Jung and Hans-Georg SahlList of participants 464Author index 470Subject index 472

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