title: Insights into the evolution of lanthipeptide biosynthesis.
abstract: Lanthipeptides are a group of posttranslationally modified peptide natural products that contain multiple thioether crosslinks. These crosslinks are formed by dehydration of Ser/Thr residues followed by addition of the thiols of Cys residues to the resulting dehydroamino acids. At least four different pathways to these polycyclic natural products have evolved, reflecting the high efficiency and evolvability of a posttranslational modification route to generate conformationally constrained peptides. The wealth of genomic information that has been made available in recent years has started to provide insights into how these remarkable pathways and their posttranslational modification machineries may have evolved. In this review, we discuss a model for the evolution of the lanthipeptide biosynthetic enzymes that has recently been developed based on the currently available data.
authors.affiliation: Department of Biochemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois, 61801.
authors.forename: Yi
authors.initials: Y
authors.lastname: Yu
authors.forename: Qi
authors.initials: Q
authors.lastname: Zhang
authors.forename: Wilfred A
authors.initials: WA
authors.lastname: van der Donk
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000096:biosynthesis / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry; D001426:Bacterial Proteins / Q000737:chemistry / Q000378:metabolism; D003500:Cyclization; D003545:Cysteine / Q000378:metabolism; D019143:Evolution, Molecular; D006836:Hydro-Lyases / Q000737:chemistry / Q000378:metabolism*; D009097:Multienzyme Complexes / Q000737:chemistry / Q000378:metabolism*; D010456:Peptides, Cyclic / Q000096:biosynthesis* / Q000737:chemistry / Q000378:metabolism; D011499:Protein Processing, Post-Translational; D012694:Serine / Q000737:chemistry; D013440:Sulfides / Q000737:chemistry*; D013912:Threonine / Q000378:metabolism
chemical_list: D000596:Amino Acids; D001426:Bacterial Proteins; D009097:Multienzyme Complexes; D010456:Peptides, Cyclic; D013440:Sulfides; D013912:Threonine; D012694:Serine; D006836:Hydro-Lyases; C099654:lanthionine synthase; C001520:lanthionine; D003545:Cysteine; D000409:Alanine
keywords: cyclic peptide; dehydration; glutamylation; kinase; labionin; lanthionine; lantibiotics; nisin; phosphothreonine lyase; posttranslational modification
references.citation: Chembiochem. 2012 May 29;13(8):1174-83
references.pmid: 22556031
references.citation: J Biol Chem. 2009 Sep 18;284(38):25962-72
references.pmid: 19620240
references.citation: Angew Chem Int Ed Engl. 2010 Mar 22;49(13):2436-40
references.pmid: 20191635
references.citation: ACS Chem Biol. 2012 Sep 21;7(9):1529-35
references.pmid: 22725258
references.citation: Chem Biol. 2008 Jan;15(1):22-31
references.pmid: 18215770
references.citation: Appl Microbiol Biotechnol. 2012 Sep;95(6):1509-17
references.pmid: 22526797
references.citation: Chemistry. 2013 Jun 10;19(24):7662-77
references.pmid: 23666908
references.citation: Angew Chem Int Ed Engl. 2010 Feb 1;49(6):1151-4
references.pmid: 20082397
references.citation: Proc Natl Acad Sci U S A. 2010 Jun 8;107(23):10430-5
references.pmid: 20479271
references.citation: Antimicrob Agents Chemother. 2011 Apr;55(4):1671-6
references.pmid: 21220527
references.citation: Proc Natl Acad Sci U S A. 2012 Nov 6;109(45):18361-6
references.pmid: 23071302
references.citation: Science. 2006 Mar 10;311(5766):1464-7
references.pmid: 16527981
references.citation: J Biol Inorg Chem. 2001 Jan;6(1):82-90
references.pmid: 11191225
references.citation: Chemistry. 2000 Apr 14;6(8):1455-66
references.pmid: 10840968
references.citation: Biochemistry. 2005 Sep 27;44(38):12827-34
references.pmid: 16171398
references.citation: Org Lett. 2002 Apr 18;4(8):1335-8
references.pmid: 11950356
references.citation: Bioorg Med Chem Lett. 2008 May 15;18(10):3025-8
references.pmid: 18294843
references.citation: Biochemistry. 2000 Feb 15;39(6):1199-204
references.pmid: 10684596
references.citation: Biochemistry. 2003 Nov 25;42(46):13613-24
references.pmid: 14622008
references.citation: Inorg Chem. 1997 Mar 12;36(6):969-978
references.pmid: 11669658
references.citation: Chem Rev. 2005 Feb;105(2):633-84
references.pmid: 15700960
references.citation: Proc Natl Acad Sci U S A. 2003 Apr 1;100(7):3695-700
references.pmid: 12649324
references.citation: Science. 2007 Feb 16;315(5814):1000-3
references.pmid: 17303758
references.citation: J Biochem. 1996 Feb;119(2):226-30
references.pmid: 8882709
references.citation: Biochemistry. 2008 Jul 15;47(28):7342-51
references.pmid: 18570437
references.citation: Nat Prod Rep. 2013 Jan;30(1):108-60
references.pmid: 23165928
references.citation: Proc Natl Acad Sci U S A. 2004 Aug 3;101(31):11448-53
references.pmid: 15277670
references.citation: Nat Chem Biol. 2013 Mar;9(3):157-9
references.pmid: 23314913
references.citation: Cell Mol Life Sci. 2008 Feb;65(3):455-76
references.pmid: 17965835
references.citation: J Bacteriol. 2002 Mar;184(6):1703-11
references.pmid: 11872722
references.citation: Curr Protein Pept Sci. 2005 Feb;6(1):77-84
references.pmid: 15638770
references.citation: Chem Rev. 2011 Jan 12;111(1):174-87
references.pmid: 21090718
references.citation: BMC Biol. 2010 May 25;8:70
references.pmid: 20500830
references.citation: PLoS One. 2013 May 28;8(5):e64010
references.pmid: 23724015
references.citation: Biochem Biophys Res Commun. 2000 Aug 18;275(1):69-74
references.pmid: 10944443
references.citation: J Am Chem Soc. 2009 Sep 2;131(34):12258-64
references.pmid: 19663480
references.citation: Inorg Chem. 2001 Nov 19;40(24):6151-7
references.pmid: 11703113
references.citation: J Am Chem Soc. 2012 Jun 20;134(24):9922-5
references.pmid: 22687055
references.citation: Nat Chem Biol. 2010 Jan;6(1):9-18
references.pmid: 20016494
references.citation: PLoS Biol. 2010 Mar 23;8(3):e1000339
references.pmid: 20351769
references.citation: Curr Biol. 1994 Jun 1;4(6):564-7
references.pmid: 7922382
references.citation: Biochemistry. 2011 Feb 8;50(5):891-8
references.pmid: 21229987
references.citation: Prog Drug Res. 2008;65:119, 121-40
references.pmid: 18084914
references.citation: J Pharmacol Toxicol Methods. 2010 Mar-Apr;61(2):210-8
references.pmid: 20176117
references.citation: J Biol Chem. 1993 Aug 5;268(22):16361-8
references.pmid: 8344922
references.citation: Gene. 2001 May 16;269(1-2):73-80
references.pmid: 11376939
references.citation: FEMS Microbiol Rev. 1993 Sep;12(1-3):39-85
references.pmid: 8398217
references.citation: Nature. 1988 May 19;333(6170):276-8
references.pmid: 2835685
references.citation: J Am Chem Soc. 2005 Nov 9;127(44):15332-3
references.pmid: 16262372
references.citation: Curr Opin Chem Biol. 1999 Apr;3(2):176-81
references.pmid: 10226042
references.citation: Drugs. 2009 Oct 1;69(14):1903-10
references.pmid: 19747007
references.citation: Chembiochem. 2012 Sep 24;13(14):2065-71
references.pmid: 22907786
references.citation: Annu Rev Biochem. 2012;81:479-505
references.pmid: 22404629
references.citation: Proc Natl Acad Sci U S A. 2013 Apr 30;110(18):7258-63
references.pmid: 23589847
references.citation: Science. 2007 Nov 9;318(5852):914; author reply 914
references.pmid: 17991845
references.citation: Biochemistry. 2000 Jul 4;39(26):7764-71
references.pmid: 10869181
references.citation: Nat Struct Mol Biol. 2004 Oct;11(10):963-7
references.pmid: 15361862
references.citation: Biochemistry. 2007 Nov 13;46(45):13179-89
references.pmid: 17929939
references.citation: Org Biomol Chem. 2003 Oct 7;1(19):3304-15
references.pmid: 14584794
references.citation: Biochemistry. 2012 May 29;51(21):4271-9
references.pmid: 22574919
references.citation: Org Lett. 2000 Nov 16;2(23):3603-6
references.pmid: 11073655