教育部合成生物学前沿科学中心,系统生物学教育部重点实验室,天津大学化工学院,天津 300350
[ "侯正杰(1995—),男,博士研究生。研究方向为生物制药、代谢工程与合成生物学。E-mail:hou_zj@tju.edu.cn" ]
[ "程景胜(1972—),男,教授,博士生导师。研究方向为生物制药、合成生物学与系统生物技术等。E-mail:jscheng@tju.edu.cn" ]
收稿:2021-01-20,
修回:2021-04-03,
纸质出版:2021-08-31
移动端阅览
侯正杰, 孙慧中, 白松, 陈新月, 曹春阳, 程景胜. 环脂肽生物合成的研究进展[J]. 合成生物学, 2021, 2(4): 577-597
HOU Zhengjie, SUN Huizhong, BAI Song, CHEN Xinyue, CAO Chunyang, CHENG Jingsheng. Research progress of cyclic lipopeptide biosynthesis[J]. Synthetic Biology Journal, 2021, 2(4): 577-597
侯正杰, 孙慧中, 白松, 陈新月, 曹春阳, 程景胜. 环脂肽生物合成的研究进展[J]. 合成生物学, 2021, 2(4): 577-597 DOI: 10.12211/2096-8280.2021-008.
HOU Zhengjie, SUN Huizhong, BAI Song, CHEN Xinyue, CAO Chunyang, CHENG Jingsheng. Research progress of cyclic lipopeptide biosynthesis[J]. Synthetic Biology Journal, 2021, 2(4): 577-597 DOI: 10.12211/2096-8280.2021-008.
环脂肽化合物是一类结构新颖的环状肽类,其两亲性的物化特性决定了其独特的生物活性,可作为抗生素、生物表面活性剂等。在生物防治、药物开发、环境修复和疾病治疗等方面广泛应用,具有迫切的市场需求和广阔的发展前景。环脂肽类天然产物主要由非核糖体肽合成途径合成,由于环脂肽合成复杂的代谢网络和前体需求、专一且严格的合成途径、多种同系物的共存,制约着环脂肽合成的微生物开发和产品价值提升。本文主要介绍了来源于细菌界的环脂肽类物质的结构特性,非核糖体肽合成途径及非核糖体肽合成酶(non-ribosomal peptide synthetase,NRPS)的结构域特点,天然产物底盘菌株开发现状,通过基因工程、代谢工程方法进行同系物调控和生物合成策略,混菌对脂肽生物合成的影响,以及合成生物学在脂肽合成中的应用。随着合成生物技术的迅速发展和运用,环脂肽类天然产物的微生物合成也有望实现“质”和“量”的提升,以及促进新型脂肽的开发。
As antibiotics and bio-surfactants
cyclic lipopeptides have unique molecular structure and biological activity and are widely applied in the fields of biological control
drug development
environmental remediation and disease treatment. It has vigorous market demand and promising future. Cyclic lipopeptides are a class of antibiotics synthesized from non-ribosomal peptide pathways by microorganisms. However
the complex metabolic network and precursor requirements
specific and strict synthetic pathway
and the coexistence of multiple homologues are restricting our capability of developing the lipopeptide syntheses potential of microorganism and promoting the product value of lipopeptide of bacteria. In this paper
we summarize the types of chassis cells for producing cyclic lipopeptides. We also introduce the structural characteristics of cyclic lipopeptides based on bacterial origin
synthesis pathway of non-ribosomal peptide
and structural domain characteristics of non-ribosomal peptide synthetase. In addition
the strategies for homologues regulation and biosynthetic yield improvement through genetic and metabolic engineering methods were reviewed
as well as the development status of natural product chassis strains. The synthesis of lipopeptide products can be effectively improved by optimizing the precursor metabolism
enhancing the expression of lipopeptide synthesis gene cluster
blocking the competitive pathway of lipopeptide synthesis
and the modification of various regulatory factors. The non-ribosomal peptide synthetase structural domain can be modified to obtain higher value lipopeptide and new lipopeptide drugs. We also review the effects of mixed-culture on lipopeptide syntheses
the development status of chassis strains for producing natural product
and the application of synthetic biology for improving lipopeptide biosynthesis. With the rapid development and application of synthetic biotechnology
the quality and quantity of natural lipopeptide from microorganisms will be improved rapidly. It also boosts the development of novel cyclic lipopeptides. And a better understanding of the synthesis
modification and mechanism of action of antimicrobial peptides will restart its commercial development.
2
LIU H-W , BEGLEY T P . Comprehensive natural products III: chemistry and biology [M ] . Amsterdam : Elsevier , 2020 .
MARTÍNEZ-NÚÑEZ M A , RODRÍGUEZ-ESCAMILLA Z . Mining the Yucatan Coastal microbiome for the identification of non-ribosomal peptides synthetase (NRPS) genes [J ] . Toxins , 2020 , 12 ( 6 ): 349 .
SCHNEIDER T , MÜLLER A , MIESS H , et al . Cyclic lipopeptides as antibacterial agents-potent antibiotic activity mediated by intriguing mode of actions [J ] . International Journal of Medical Microbiology , 2014 , 304 ( 1 ): 37 - 43 .
FELNAGLE E A , JACKSON E E , CHAN Y A , et al . Nonribosomal peptide synthetases involved in the production of medically relevant natural products [J ] . Molecular Pharmaceutics , 2008 , 5 ( 2 ): 191 - 211 .
NATION R L , LI J , CARS O , et al . Framework for optimisation of the clinical use of colistin and polymyxin B: the Prato polymyxin consensus [J ] . The Lancet Infectious Diseases , 2015 , 15 ( 2 ): 225 - 234 .
LIU Y Y , WANG Y , WALSH T R , et al . Emergence of plasmid-mediated colistin resistance mechanism MCR-1 in animals and human beings in China: a microbiological and molecular biological study [J ] . The Lancet Infectious Diseases , 2016 , 16 ( 2 ): 161 - 168 .
DI PILATO V , ARENA F , TASCINI C , et al . mcr-1.2, A new mcr variant carried on a transferable plasmid from a colistin-resistant KPC carbapenemase-producing Klebsiella pneumoniae strain of sequence type 512 [J ] . Antimicrobial Agents and Chemotherapy , 2016 , 60 ( 9 ): 5612 - 5615 .
BRINK A J , RICHARDS G A , COLOMBO G , et al . Multicomponent antibiotic substances produced by fermentation: implications for regulatory authorities, critically ill patients and generics [J ] . International Journal of Antimicrobial Agents , 2014 , 43 ( 1 ): 1 - 6 .
VELKOV T , GALLARDO-GODOY A , SWARBRICK J D , et al . Structure, function, and biosynthetic origin of octapeptin antibiotics active against extensively drug-resistant Gram-negative bacteria [J ] . Cell Chemical Biology , 2018 , 25 ( 4 ): 380 - 391.e5 .
ZEITLINGER M A , DERENDORF H , MOUTON J W , et al . Protein binding: do we ever learn? [J ] . Antimicrobial Agents and Chemotherapy , 2011 , 55 ( 7 ): 3067 - 3074 .
SIRIWARDENA T N , STACH M , HE R , et al . Lipidated peptide dendrimers killing multidrug-resistant bacteria [J ] . Journal of the American Chemical Society , 2018 , 140 ( 1 ): 423 - 432 .
BALTZ R H . Combinatorial biosynthesis of cyclic lipopeptide antibiotics: a model for synthetic biology to accelerate the evolution of secondary metabolite biosynthetic pathways [J ] . ACS Synthetic Biology , 2014 , 3 ( 10 ): 748 – 758 .
INÈS M , DHOUHA G . Lipopeptide surfactants: production, recovery and pore forming capacity [J ] . Peptides , 2015 , 71 : 100 - 112 .
TALLY F P , DEBRUIN M F . Development of daptomycin for Gram-positive infections [J ] . Journal of Antimicrobial Chemotherapy , 2000 , 46 ( 4 ): 523 - 526 .
TRIMBLE M J , MLYNÁRČIK P , KOLÁŘ M , et al . Polymyxin: Alternative mechanisms of action and resistance [J ] . Cold Spring Harbor Perspectives in Medicine , 2016 , 6 ( 10 ): a025288 .
KÜGLER J H , LE ROES-HILL M , SYLDATK C , et al . Surfactants tailored by the class Actinobacteria [J ] . Frontiers in Microbiology , 2015 , 6 : 212 .
ONGENA M , JACQUES P . Bacillus lipopeptides: versatile weapons for plant disease biocontrol [J ] . Trends in Microbiology , 2008 , 16 ( 3 ): 115 – 125 .
GROSS H , LOPER J E . Genomics of secondary metabolite production by Pseudomonas spp [J ] . Natural Product Reports , 2009 , 26 ( 11 ): 1408 - 1446 .
BANAT I M , FRANZETTI A , GANDOLFI I , et al . Microbial biosurfactants production, applications and future potential [J ] . Applied Microbiology and Biotechnology , 2010 , 87 ( 2 ): 427 - 444 .
COCHRANE S A , VEDERAS J C . Lipopeptides from Bacillus and Paenibacillus spp. a gold mine of antibiotic candidates [J ] . Medicinal Research Reviews , 2016 , 36 ( 1 ): 4 - 31 .
MARAHIEL M A . A structural model for multimodular NRPS assembly lines [J ] . Natural Product Reports , 2016 , 33 ( 2 ): 136 - 140 .
ZHANG F L , WANG Y K , JIANG Q , et al . Substrate selection of adenylation domains for nonribosomal peptide synthetase (NRPS) in bacillamide C biosynthesis by marine Bacillus atrophaeus C89 [J ] . Journal of Industrial Microbiology & Biotechnology , 2018 , 45 ( 5 ): 335 - 344 .
BUMPUS S B , EVANS B S , THOMAS P M , et al . A proteomics approach to discovering natural products and their biosynthetic pathways [J ] . Nature Biotechnology , 2009 , 27 ( 10 ): 951 - 956 .
MEIER J L , NIESSEN S , HOOVER H S , et al . An orthogonal active site identification system (OASIS) for proteomic profiling of natural product biosynthesis [J ] . ACS Chemical Biology , 2009 , 4 ( 11 ): 948 - 957 .
ISHIKAWA F , TANABE G . Chemical strategies for visualizing and analyzing endogenous nonribosomal peptide synthetase (NRPS) megasynthetases [J ] . Chembiochem , 2019 , 20 ( 16 ): 2032 - 2040 .
肖丽萍 , 邓子新 , 刘天罡 . 链霉菌底盘细胞的开发现状及其应用 [J ] . 微生物学报 , 2016 , 56 ( 3 ): 441 - 453 .
XIAO L P , DENG Z X , LIU T G . Progress in developing and applying Streptomyces chassis - a review [J ] . Acta Microbiologica Sinica , 2016 , 56 ( 3 ): 441 - 453 .
卜庆廷 . 基于恰塔努加链霉菌的聚酮类底盘细胞构建与评估 [D ] . 杭州 : 浙江大学 , 2019 .
BU Q T . Construction and evaluation of polyketide chassis derived from Streptomyces chattanoogensis [D ] . Hangzhou : Zhejiang University , 2019 .
GEYS R , SOETAERT W , VAN BOGAERT I . Biotechnological opportunities in biosurfactant production [J ] . Current Opinion in Biotechnology , 2014 , 30 : 66 - 72 .
KOSARIC N , VARDAR-SUKAN F . Biosurfactants: production and applications [M ] . Boca Raton : CRC Press , 2014 .
KOMATSU M , KOMATSU K , KOIWAI H , et al . Engineered Streptomyces avermitilis host for heterologous expression of biosynthetic gene cluster for secondary metabolites [J ] . ACS Synthetic Biology , 2013 , 2 ( 7 ): 384 - 396 .
LIU Q , XIAO L P , ZHOU Y J , et al . Development of Streptomyces sp. FR-008 as an emerging chassis [J ] . Synthetic and Systems Biotechnology , 2016 , 1 ( 3 ): 207 - 214 .
TAN B , ZHANG Q B , ZHU Y G , et al . Deciphering biosynthetic enzymes leading to 4-chloro-6-methyl-5,7-dihydroxyphenylglycine, a non-proteinogenic amino acid in totopotensamides [J ] . ACS Chemical Biology , 2020 , 15 ( 3 ): 766 - 773 .
BALTZ R H . Correction to: synthetic biology, genome mining, and combinatorial biosynthesis of NRPS‑derived antibiotics: a perspective [J ] . Journal of Industrial Microbiology & Biotechnology , 2018 , 45 ( 7 ): 651 - 655 .
ZHANG M M , WANG Y , ANG E L , et al . Engineering microbial hosts for production of bacterial natural products [J ] . Natural Product Reports , 2016 , 33 ( 8 ): 963 - 987 .
WANG X , ZHOU H B , CHEN H N , et al . Discovery of recombinases enables genome mining of cryptic biosynthetic gene clusters in Burkholderiales species [J ] . Proceedings of the National Academy of Sciences of the United States of America , 2018 , 115 ( 18 ): E4255 - E4263 .
ZHI Y , WU Q , XU Y . Genome and transcriptome analysis of surfactin biosynthesis in Bacillus amyloliquefaciens MT45 [J ] . Scientific Reports , 2017 , 7 : 40976 .
WU Q , ZHI Y , XU Y . Systematically engineering the biosynthesis of a green biosurfactant surfactin by Bacillus subtilis 168 [J ] . Metabolic Engineering , 2019 , 52 : 87 - 97 .
HÜHNER E , BACKHAUS K , KRAUT R , et al . Production of α -keto carboxylic acid dimers in yeast by overexpression of NRPS-like genes from Aspergillus terreus [J ] . Applied Microbiology and Biotechnology , 2018 , 102 ( 4 ): 1663 - 1672 .
NAH H J , PYEON H R , KANG S H , et al . Cloning and heterologous expression of a large-sized natural product biosynthetic gene cluster in Streptomyces species [J ] . Frontiers in Microbiology , 2017 , 8 : 394 .
HACKER C , CAI X , KEGLER C , et al . Structure-based redesign of docking domain interactions modulates the product spectrum of a rhabdopeptide-synthesizing NRPS [J ] . Nature Communications , 2018 , 9 ( 1 ): 4366 .
BALTZ R H . Synthetic biology, genome mining, and combinatorial biosynthesis of NRPS-derived antibiotics: a perspective [J ] . Journal of Industrial Microbiology & Biotechnology , 2018 , 45 ( 7 ): 635 - 649 .
GRADY E N , MACDONALD J , LIU L D , et al . Current knowledge and perspectives of Paenibacillus : a review [J ] . Microbial Cell Factories , 2016 , 15 ( 1 ): 203 .
TAMBADOU F , CARADEC T , GAGEZ A L , et al . Characterization of the colistin (polymyxin E1 and E2) biosynthetic gene cluster [J ] . Archives of Microbiology , 2015 , 197 ( 4 ): 521 - 532 .
KWA A L , LIM T P , LOW J G , et al . Pharmacokinetics of polymyxin B1 in patients with multidrug-resistant Gram-negative bacterial infections [J ] . Diagnostic Microbiology and Infectious Disease , 2008 , 60 ( 2 ): 163 - 167 .
HE H , LI J C , NATION R L , et al . Pharmacokinetics of four different brands of colistimethate and formed colistin in rats [J ] . Journal of Antimicrobial Chemotherapy , 2013 , 68 ( 10 ): 2311 - 2317 .
SIVANESAN S , ROBERTS K , WANG J P , et al . Pharmacokinetics of the individual major components of polymyxin B and colistin in rats [J ] . Journal of Natural Products , 2017 , 80 ( 1 ): 225 - 229 .
ROBERTS K D , AZAD M A K , WANG J P , et al . Antimicrobial activity and toxicity of the major lipopeptide components of polymyxin B and colistin: last-line antibiotics against multidrug-resistant Gram-negative bacteria [J ] . ACS Infectious Diseases , 2015 , 1 ( 11 ): 568 - 575 .
MEDEMA M H , CIMERMANCIC P , SALI A , et al . A systematic computational analysis of biosynthetic gene cluster evolution: lessons for engineering biosynthesis [J ] . PLoS Computational Biology , 2014 , 10 ( 12 ): e1004016 .
YAN F , BURGARD C , POPOFF A , et al . Synthetic biology approaches and combinatorial biosynthesis towards heterologous lipopeptide production [J ] . Chemical Science , 2018 , 9 ( 38 ): 7510 - 7519 .
MINGEOT-LECLERCQ M P , TULKENS P M , DENAMUR S , et al . Novel polymyxin derivatives are less cytotoxic than polymyxin B to renal proximal tubular cells [J ] . Peptides , 2012 , 35 ( 2 ): 248 - 252 .
VAARA M , SADER H S , RHOMBERG P R , et al . Antimicrobial activity of the novel polymyxin derivative NAB739 tested against Gram-negative pathogens [J ] . Journal of Antimicrobial Chemotherapy , 2013 , 68 ( 3 ): 636 - 639 .
SCHAUWECKER F , PFENNIG F , GRAMMEL N , et al . Construction and in vitro analysis of a new bi-modular polypeptide synthetase for synthesis of N -methylated acyl peptides [J ] . Chemistry & Biology , 2000 , 7 ( 4 ): 287 - 297 .
ZHANG K , NELSON K M , BHURIPANYO K , et al . Engineering the substrate specificity of the DhbE adenylation domain by yeast cell surface display [J ] . Chemistry & Biology , 2013 , 20 ( 1 ): 92 - 101 .
DUERFAHRT T , EPPELMANN K , MÜLLER R , et al . Rational design of a bimodular model system for the investigation of heterocyclization in nonribosomal peptide biosynthesis [J ] . Chemistry & Biology , 2004 , 11 ( 2 ): 261 - 271 .
THIRLWAY J , LEWIS R , NUNNS L , et al . Introduction of a non-natural amino acid into a nonribosomal peptide antibiotic by modification of adenylation domain specificity [J ] . Angewandte Chemie (International Ed in English) , 2012 , 51 ( 29 ): 7181 - 7184 .
HEIDE L , WESTRICH L , ANDERLE C , et al . Use of a halogenase of hormaomycin biosynthesis for formation of new clorobiocin analogues with 5-chloropyrrole moieties [J ] . ChembioChem , 2008 , 9 ( 12 ): 1992 - 1999 .
NGUYEN K T , RITZ D , GU J-Q , et al . Combinatorial biosynthesis of novel antibiotics related to daptomycin [J ] . Proceedings of the National Academy of Sciences of the United States of America , 2006 , 103 ( 46 ): 17462 - 17467 .
FISCHBACH M A , LAI J R , ROCHE E D , et al . Directed evolution can rapidly improve the activity of chimeric assembly-line enzymes [J ] . Proceedings of the National Academy of Sciences of the United States of America , 2007 , 104 ( 29 ): 11951 - 11956 .
HAN J W , KIM E Y , LEE J M , et al . Site-directed modification of the adenylation domain of the fusaricidin nonribosomal peptide synthetase for enhanced production of fusaricidin analogs [J ] . Biotechnology Letters , 2012 , 34 ( 7 ): 1327 - 1334 .
KRIES H , NIQUILLE D L , HILVERT D . A subdomain swap strategy for reengineering nonribosomal peptides [J ] . Chemistry & Biology , 2015 , 22 ( 5 ): 640 - 648 .
BIAN X Y , PLAZA A , YAN F , et al . Rational and efficient site-directed mutagenesis of adenylation domain alters relative yields of luminmide derivatives in vivo [J ] . Biotechnology and Bioengineering , 2015 , 112 ( 7 ): 1343 - 1353 .
KIM S Y , PARK S Y , CHOI S K , et al . Biosynthesis of polymyxins B, E, and P using genetically engineered polymyxin synthetases in the surrogate host Bacillus subtilis [J ] . Journal of Microbiology and Biotechnology , 2015 , 25 ( 7 ): 1015 - 1025 .
CALCOTT M J , OWEN J G , LAMONT I L , et al . Biosynthesis of novel Pyoverdines by domain substitution in a nonribosomal peptide synthetase of Pseudomonas aeruginosa [J ] . Applied and Environmental Microbiology , 2014 , 80 ( 18 ): 5723 - 5731 .
CALCOTT M J , ACKERLEY D F . Portability of the thiolation domain in recombinant pyoverdine non-ribosomal peptide synthetases [J ] . BMC Microbiology , 2015 , 15 : 162 .
STACHELHAUS T , SCHNEIDER A , MARAHIEL M A . Rational design of peptide antibiotics by targeted replacement of bacterial and fungal domains [J ] . Science , 1995 , 269 ( 5220 ): 69 - 72 .
YAKIMOV M M , GIULIANO L , TIMMIS K N , et al . Recombinant acylheptapeptide lichenysin: high level of production by Bacillus subtilis cells [J ] . Journal of Molecular Microbiology and Biotechnology , 2000 , 2 ( 2 ): 217 - 224 .
EPPELMANN K , STACHELHAUS T , MARAHIEL M A . Exploitation of the selectivity-conferring code of nonribosomal peptide synthetases for the rational design of novel peptide antibiotics [J ] . Biochemistry , 2002 , 41 ( 30 ): 9718 - 9726 .
MOOTZ H D , KESSLER N , LINNE U , et al . Decreasing the ring size of a cyclic nonribosomal peptide antibiotic by in-frame module deletion in the biosynthetic genes [J ] . Journal of the American Chemical Society , 2002 , 124 ( 37 ): 10980 - 10981 .
SCHWARZER D , MOOTZ H D , MARAHIEL M A . Exploring the impact of different thioesterase domains for the design of hybrid peptide synthetases [J ] . Chemistry & Biology , 2001 , 8 ( 10 ): 997 - 1010 .
MOOTZ H D , SCHWARZER D , MARAHIEL M A . Construction of hybrid peptide synthetases by module and domain fusions [J ] . Proceedings of the National Academy of Sciences of the United States of America , 2000 , 97 ( 11 ): 5848 - 5853 .
ZHAO H B , SHAO D Y , JIANG C M , et al . Biological activity of lipopeptides from Bacillus [J ] . Applied Microbiology and Biotechnology , 2017 , 101 ( 15 ): 5951 - 5960 .
COUTTE F , LECOUTURIER D , DIMITROV K , et al . Microbial lipopeptide production and purification bioprocesses, current progress and future challenges [J ] . Biotechnology Journal , 2017 , 12 ( 7 ): 1600566 .
WANG M M , YU H M , SHEN Z Y . Antisense RNA-based strategy for enhancing surfactin production in Bacillus subtilis TS1726 via overexpression of the unconventional biotin carboxylase II to enhance ACCase activity [J ] . ACS Synthetic Biology , 2019 , 8 ( 2 ): 251 - 256 .
DANG Y L , ZHAO F J , LIU X S , et al . Enhanced production of antifungal lipopeptide iturin A by Bacillus amyloliquefaciens LL3 through metabolic engineering and culture conditions optimization [J ] . Microbial Cell Factories , 2019 , 18 ( 1 ): 1 - 14 .
XU Y X , CAI D B , ZHANG H , et al . Enhanced production of iturin A in Bacillus amyloliquefaciens by genetic engineering and medium optimization [J ] . Process Biochemistry , 2020 , 90 : 50 - 57 .
HUANG X W , MA T M , TIAN J , et al . wblA, a pleiotropic regulatory gene modulating morphogenesis and daptomycin production in Streptomyces roseosporus [J ] . Journal of Applied Microbiology , 2017 , 123 ( 3 ): 669 - 677 .
STEVENS B W , JOSKA T M , ANDERSON A C . Progress toward re-engineering non-ribosomal peptide synthetase proteins: a potential new source of pharmacological agents [J ] . Drug Development Research , 2005 , 66 ( 1 ): 9 - 18 .
UGURU G C , MILNE C , BORG M , et al . Active-site modifications of adenylation domains lead to hydrolysis of upstream nonribosomal peptidyl thioester intermediates [J ] . Journal of the American Chemical Society , 2004 , 126 ( 16 ): 5032 - 5033 .
BELSHAW P J , WALSH C T , STACHELHAUS T . Aminoacyl-CoAs as probes of condensation domain selectivity in nonribosomal peptide synthesis [J ] . Science , 1999 , 284 ( 5413 ): 486 - 489 .
ACKERLEY D F , LAMONT I L . Characterization and genetic manipulation of peptide synthetases in Pseudomonas aeruginosa PAO1 in order to generate novel pyoverdines [J ] . Chemistry & Biology , 2004 , 11 ( 7 ): 971 - 980 .
DE FERRA F , RODRIGUEZ F , TORTORA O , et al . Engineering of peptide synthetases. Key role of the thioesterase-like domain for efficient production of recombinant peptides [J ] . Journal of Biological Chemistry , 1997 , 272 ( 40 ): 25304 - 25309 .
DUERFAHRT T , DOEKEL S , SONKE T , et al . Construction of hybrid peptide synthetases for the production of α -l-aspartyl-l-phenylalanine, a precursor for the high-intensity sweetener aspartame [J ] . European Journal of Biochemistry , 2003 , 270 ( 22 ): 4555 - 4563 .
BUTZ D , SCHMIEDERER T , HADATSCH B , et al . Module extension of a non-ribosomal peptide synthetase of the glycopeptide antibiotic balhimycin produced by Amycolatopsis balhimycina [J ] . ChemBioChem , 2008 , 9 ( 8 ): 1195 - 1200 .
CHOOI Y H , TANG Y . Adding the lipo to lipopeptides: do more with less [J ] . Chemistry & Biology , 2010 , 17 ( 8 ): 791 - 793 .
SHAHEEN M , LI J , ROSS A C , et al . Paenibacillus polymyxa PKB 1 produces variants of polymyxin B-type antibiotics [J ] . Chemistry & Biology , 2011 , 18 ( 12 ): 1640 - 1648 .
NIU B , VATER J , RUECKERT C , et al . Polymyxin P is the active principle in suppressing phytopathogenic Erwinia spp. by the biocontrol rhizobacterium Paenibacillus polymyxa M-1 [J ] . BMC Microbiology , 2013 , 13 ( 1 ): 1 - 13 .
GALEA C A , HAN M L , ZHU Y , et al . Characterization of the polymyxin D synthetase biosynthetic cluster and product profile of Paenibacillus polymyxa ATCC 10401 [J ] . Journal of Natural Products , 2017 , 80 ( 5 ): 1264 - 1274 .
BLOUDOFF K , RODIONOV D , SCHMEING T M . Crystal structures of the first condensation domain of CDA synthetase suggest conformational changes during the synthetic cycle of nonribosomal peptide synthetases [J ] . Journal of Molecular Biology , 2013 , 425 ( 17 ): 3137 - 3150 .
MÜLLER A , WENZEL M , STRAHL H , et al . Daptomycin inhibits cell envelope synthesis by interfering with fluid membrane microdomains [J ] . Proceedings of the National Academy of Sciences of the United States of America , 2016 , 113 ( 45 ): E7077 - E7086 .
BALTZ R H , MIAO V , WRIGLEY S K . Natural products to drugs: daptomycin and related lipopeptide antibiotics [J ] . Natural Product Reports , 2005 , 22 ( 6 ): 717 - 741 .
LIU T Q , ZHU N Y , ZHONG C , et al . Effect of N -methylated and fatty acid conjugation on analogs of antimicrobial peptide Anoplin [J ] . European Journal of Pharmaceutical Sciences , 2020 , 152 : 105453 .
DHALI D , COUTTE F , ARIAS A A , et al . Genetic engineering of the branched fatty acid metabolic pathway of Bacillus subtilis for the overproduction of surfactin C 14 isoform [J ] . Biotechnology Journal , 2017 , 12 ( 7 ): 1600574 .
LIU Q , FAN W J , ZHAO Y J , et al . Probing and engineering the fatty acyl substrate selectivity of starter condensation domains of nonribosomal peptide synthetases in lipopeptide biosynthesis [J ] . Biotechnology Journal , 2020 , 15 ( 2 ): e1900175 .
FAN W J , LIU H , LIU P P , et al . Characterization of protein interaction surface on fatty acyl selectivity of starter condensation domain in lipopeptide biosynthesis [J ] . Applied Microbiology and Biotechnology , 2020 , 104 ( 2 ): 653 - 660 .
NGUYEN K T , HE X W , ALEXANDER D C , et al . Genetically engineered lipopeptide antibiotics related to A54145 and daptomycin with improved properties [J ] . Antimicrobial Agents and Chemotherapy , 2010 , 54 ( 4 ): 1404 - 1413 .
HANSEN D B , BUMPUS S B , ARON Z D , et al . The loading module of mycosubtilin: an adenylation domain with fatty acid selectivity [J ] . Journal of the American Chemical Society , 2007 , 129 ( 20 ): 6366 - 6367 .
DING L S , GUO W B , CHEN X H . Exogenous addition of alkanoic acids enhanced production of antifungal lipopeptides in Bacillus amyloliquefaciens Pc3 [J ] . Applied Microbiology and Biotechnology , 2019 , 103 ( 13 ): 5367 - 5377 .
ZHOU D Y , HU F X , LIN J Z , et al . Genome and transcriptome analysis of Bacillus velezensis BS-37, an efficient surfactin producer from glycerol, in response to D-/L-leucine [J ] . MicrobiologyOpen , 2019 , 8 ( 8 ): e00794 .
WU J Y , LIAO J H , SHIEH C J , et al . Kinetic analysis on precursors for iturin A production from Bacillus amyloliquefaciens BPD1 [J ] . Journal of Bioscience and Bioengineering , 2018 , 126 ( 5 ): 630 - 635 .
KATO H , NISHIYAMA H , NAKAO K , et al . Pressor effects of orally administered beta-adrenergic receptor blocking agents in consciou spontaneously hypertensive rats [J ] . Japanese Journal of Pharmacology , 1976 , 26 ( 6 ): 772 - 775 .
BARTAL A , VIGNESHWARI A , BÓKA B , et al . Effects of different cultivation parameters on the production of surfactin variants by a Bacillus subtilis strain [J ] . Molecules , 2018 , 23 ( 10 ): 2675 .
LYHS U , KATZAV M , ISOHANNI P , et al . The temporal, PFGE and resistance pattern associations suggest that poultry products are only a minor source of human infections in western Finland [J ] . Food Microbiology , 2010 , 27 ( 2 ): 311 - 315 .
LIN H-Y , RAO Y , WU W-S , et al . Ferrous ion enhanced lipopeptide antibiotic iturin A production from Bacillus amyloliquefaciens B128 [J ] . International Journal of Applied Science and Engineering , 2007 , 2 : 123 - 132 .
COOPER D G , MACDONALD C R , DUFF S J , et al . Enhanced production of surfactin form Bacillus subtilis by continous product removal and metal cation additions [J ] . Applied and Environmental Microbiology , 1981 , 42 ( 3 ): 408 - 412 .
BESSON F , HOURDOU M-L , MICHEL G . Studies on the biosynthesis of iturin, an antibiotic of Bacillus subtilis , and alipopeptide containing β -hydroxy fatty acids [J ] . Biochimica et Biophysica Acta (BBA)-General Subjects , 1990 , 1036 ( 2 ): 101 - 106 .
ZHOU S N , LIU G , ZHENG R K , et al . Structural and functional insights into iturin W, a novel lipopeptide produced by the deep-sea bacterium Bacillus sp. strain wsm-1 [J ] . Applied and Environmental Microbiology , 2020 , 86 ( 21 ): e01597-20 .
BESSON F , HOURDOU M L . Effect of amino acids on the biosynthesis of β -amino acids, constituents of bacillomycins F [J ] . The Journal of Antibiotics , 1987 , 40 ( 2 ): 221 - 223 .
RAVI A , NANDAYIPURATH V V T , RAJAN S , et al . Effect of zinc oxide nanoparticle supplementation on the enhanced production of surfactin and iturin lipopeptides of endophytic Bacillus sp. Fcl1 and its ameliorated antifungal activity [J ] . Pest Management Science , 2021 , 77 ( 2 ): 1035 - 1041 .
YUAN Y , XU Q M , YU S C , et al . Control of the polymyxin analog ratio by domain swapping in the nonribosomal peptide synthetase of Paenibacillus polymyxa [J ] . Journal of Industrial Microbiology & Biotechnology , 2020 , 47 ( 6/7 ): 551 - 562 .
KRAAS F I , HELMETAG V , WITTMANN M , et al . Functional dissection of surfactin synthetase initiation module reveals insights into the mechanism of lipoinitiation [J ] . Chemistry & Biology , 2010 , 17 ( 8 ): 872 - 880 .
SCHNEIDER A , STACHELHAUS T , MARAHIEL M A . Targeted alteration of the substrate specificity of peptide synthetases by rational module swapping [J ] . Molecular and General Genetics MGG , 1998 , 257 ( 3 ): 308 - 318 .
JIANG J , GAO L , BIE X M , et al . Identification of novel surfactin derivatives from NRPS modification of Bacillus subtilis and its antifungal activity against Fusarium moniliforme [J ] . BMC Microbiology , 2016 , 16 ( 1 ): 1 - 14 .
SIEBER S A , MARAHIEL M A . Learning from nature's drug factories: nonribosomal synthesis of macrocyclic peptides [J ] . Journal of Bacteriology , 2003 , 185 ( 24 ): 7036 - 7043 .
VILLEGAS-ESCOBAR V , CEBALLOS I , MIRA J J , et al . fengycin C produced by Bacillus subtilis EA-CB0015 [J ] . Journal of Natural Products , 2013 , 76 ( 4 ): 503 – 509 .
SANG-CHEOL L , KIM S H , PARK I H , et al . Isolation, purification, and characterization of novel fengycin S from Bacillus amyloliquefaciens LSC04 degrading-crude oil [J ] . Biotechnology and Bioprocess Engineering , 2010 , 15 ( 2 ): 246 - 253 .
GAO L , GUO J P , FAN Y , et al . Module and individual domain deletions of NRPS to produce plipastatin derivatives in Bacillus subtilis [J ] . Microbial Cell Factories , 2018 , 17 ( 1 ): 84 .
GONG A D , LI H P , YUAN Q S , et al . Antagonistic mechanism of iturin A and plipastatin A from Bacillus amyloliquefaciens S76-3 from wheat spikes against Fusarium graminearum [J ] . PLoS One , 2015 , 10 ( 2 ): e0116871 .
MA Z W , HU J C . Plipastatin A1 produced by a marine sediment-derived Bacillus amyloliquefaciens SH-B74 contributes to the control of gray mold disease in tomato [J ] . 3 Biotech , 2018 , 8 ( 2 ): 1 - 10 .
GAO L , LIU H X , MA Z , et al . Translocation of the thioesterase domain for the redesign of plipastatin synthetase [J ] . Scientific Reports , 2016 , 6 : 38467 .
TAYLOR S D , PALMER M . The action mechanism of daptomycin [J ] . Bioorganic & Medicinal Chemistry , 2016 , 24 ( 24 ): 6253 - 6268 .
BALTZ R H . Biosynthesis and genetic engineering of lipopeptides in Streptomyces roseosporus [M ] // Complex enzymes in microbial natural product biosynthesis , part a : overview articles and peptides. Elsevier , 2009 : 511 - 531 .
HUBER F M , PIEPER R L , TIETZ A J . The formation of daptomycin by supplying decanoic acid to Streptomyces roseosporus cultures producing the antibiotic complex A21978C [J ] . Journal of Biotechnology , 1988 , 7 ( 4 ): 283 - 292 .
KAWAGOE Y , SHIRAISHI S , KONDO H , et al . Cyclic lipopeptide iturin A structure-dependently induces defense response in Arabidopsis plants by activating SA and JA signaling pathways [J ] . Biochemical and Biophysical Research Communications , 2015 , 460 ( 4 ): 1015 - 1020 .
罗帅 . 达托霉素优质高效生物合成的调控机制研究 [D ] . 杭州 : 浙江大学 , 2018 .
LUO S . The regulatory mechanisms of daptomycin in biosynthesis in high-quality and efficiency [D ] . Hangzhou : Zhejiang University , 2018 .
ONAKA H , MORI Y , IGARASHI Y , et al . Mycolic acid-containing bacteria induce natural-product biosynthesis in Streptomyces species [J ] . Applied and Environmental Microbiology , 2011 , 77 ( 2 ): 400 - 406 .
ALVES A R , SEQUEIRA A M , CUNHA Â . Increase in bacterial biosurfactant production by co-cultivation with biofilm-forming bacteria [J ] . Letters in Applied Microbiology , 2019 , 69 ( 1 ): 79 - 86 .
WOŹNIAK-KARCZEWSKA M , MYSZKA K , SZNAJDROWSKA A , et al . Isolation of rhamnolipids-producing cultures from faeces: influence of interspecies communication on the yield of rhamnolipid congeners [J ] . New Biotechnology , 2017 , 36 : 17 - 25 .
WU Q , NI M , DOU K , et al . Co-culture of Bacillus amyloliquefaciens ACCC11060 and Trichoderma asperellum GDFS1009 enhanced pathogen-inhibition and amino acid yield [J ] . Microbial Cell Factories , 2018 , 17 ( 1 ): 155 .
MNIF I , MNIF S , SAHNOUN R , et al . Biodegradation of diesel oil by a novel microbial consortium: comparison between co-inoculation with biosurfactant-producing strain and exogenously added biosurfactants [J ] . Environmental Science and Pollution Research , 2015 , 22 ( 19 ): 14852 - 14861 .
GÖTZE S , HERBST-IRMER R , KLAPPER M , et al . Structure, biosynthesis, and biological activity of the cyclic lipopeptide Anikasin [J ] . ACS Chemical Biology , 2017 , 12 ( 10 ): 2498 - 2502 .
GOERING A W , LI J , MCCLURE R A , et al . In vitro reconstruction of nonribosomal peptide biosynthesis directly from DNA using cell-free protein synthesis [J ] . ACS Synthetic Biology , 2017 , 6 ( 1 ): 39 - 44 .
0
浏览量
1
下载量
1
CSCD
关联资源
相关文章
相关作者
相关机构
京公网安备11010802024621