Show legend Show as text

Structure type: monomer
Trivial name: polyoxin A
Compound class: glycoside

• Article ID: 5368
  Zhai L, Lin S, Qu D, Hong X, Bai L, Chen W, Deng Z "Engineering of an industrial polyoxin producer for the rational production of hybrid peptidyl nucleoside antibiotics" - Metabolic Engineering 14(4) (2012) 388-393
  

  Polyoxins and nikkomycins are potent antifungal peptidyl nucleoside antibiotics, which inhibit fungal cell wall biosynthesis. They consist of a nucleoside core and one or two independent peptidyl moieties attached to the core at different sites. Making mutations and introducing heterologous genes into an industrial Streptomyces aureochromogenes polyoxin producer, resulted in the production of four polyoxin-nikkomycin hybrid antibiotics designated as polyoxin N and nikkoxin B-D, whose structures were confirmed using high resolution MS and NMR. Two of the hybrid antibiotics, polyoxin N and nikkoxin D, were significantly more potent against some human or plant fungal pathogens than their parents. The data provides an example for rational generation of novel peptidyl nucleoside antibiotics in an industrial producer.

  Streptomyces aureochromogenes YB172, Streptomyces tendae Tü901/8c, nikkomycin, antifungal antibiotics, chitinase inhibitors

  NCBI PubMed ID: 22465029
  Publication DOI: 10.1016/j.ymben.2012.03.006
  Journal NLM ID: 9815657
  Publisher: Brugge, Belgium; Orlando, FL: Academic Press
  Correspondence: Chen W ; Deng Z
  Institutions: State Key Laboratory of Microbial Metabolism, and School of Life Sciences & Biotechnology, Shanghai Jiao Tong University, Shanghai, China, Key Laboratory of Combinatorial Biosynthesis and Drug Discovery (Wuhan University), Ministry of Education, and Wuhan University School of Pharmaceutical Sciences, Wuhan, China
  Methods: 13C NMR, 1H NMR, NMR-2D, DNA techniques, MS/MS, extraction, cloning, ESI-QTOF-MS, antifungal activity test
  
   
  
  Streptomyces aureochromogenes YB172
  CSDB ID 45972 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: nikkomycin I
Compound class: glycoside

• Article ID: 5368
  Zhai L, Lin S, Qu D, Hong X, Bai L, Chen W, Deng Z "Engineering of an industrial polyoxin producer for the rational production of hybrid peptidyl nucleoside antibiotics" - Metabolic Engineering 14(4) (2012) 388-393
  

  Polyoxins and nikkomycins are potent antifungal peptidyl nucleoside antibiotics, which inhibit fungal cell wall biosynthesis. They consist of a nucleoside core and one or two independent peptidyl moieties attached to the core at different sites. Making mutations and introducing heterologous genes into an industrial Streptomyces aureochromogenes polyoxin producer, resulted in the production of four polyoxin-nikkomycin hybrid antibiotics designated as polyoxin N and nikkoxin B-D, whose structures were confirmed using high resolution MS and NMR. Two of the hybrid antibiotics, polyoxin N and nikkoxin D, were significantly more potent against some human or plant fungal pathogens than their parents. The data provides an example for rational generation of novel peptidyl nucleoside antibiotics in an industrial producer.

  Streptomyces aureochromogenes YB172, Streptomyces tendae Tü901/8c, nikkomycin, antifungal antibiotics, chitinase inhibitors

  NCBI PubMed ID: 22465029
  Publication DOI: 10.1016/j.ymben.2012.03.006
  Journal NLM ID: 9815657
  Publisher: Brugge, Belgium; Orlando, FL: Academic Press
  Correspondence: Chen W ; Deng Z
  Institutions: State Key Laboratory of Microbial Metabolism, and School of Life Sciences & Biotechnology, Shanghai Jiao Tong University, Shanghai, China, Key Laboratory of Combinatorial Biosynthesis and Drug Discovery (Wuhan University), Ministry of Education, and Wuhan University School of Pharmaceutical Sciences, Wuhan, China
  Methods: 13C NMR, 1H NMR, NMR-2D, DNA techniques, MS/MS, extraction, cloning, ESI-QTOF-MS, antifungal activity test
  
   
  
  Streptomyces tendae Tü901/8c
  CSDB ID 45973 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: nikkomycin J
Compound class: glycoside

• Article ID: 5368
  Zhai L, Lin S, Qu D, Hong X, Bai L, Chen W, Deng Z "Engineering of an industrial polyoxin producer for the rational production of hybrid peptidyl nucleoside antibiotics" - Metabolic Engineering 14(4) (2012) 388-393
  

  Polyoxins and nikkomycins are potent antifungal peptidyl nucleoside antibiotics, which inhibit fungal cell wall biosynthesis. They consist of a nucleoside core and one or two independent peptidyl moieties attached to the core at different sites. Making mutations and introducing heterologous genes into an industrial Streptomyces aureochromogenes polyoxin producer, resulted in the production of four polyoxin-nikkomycin hybrid antibiotics designated as polyoxin N and nikkoxin B-D, whose structures were confirmed using high resolution MS and NMR. Two of the hybrid antibiotics, polyoxin N and nikkoxin D, were significantly more potent against some human or plant fungal pathogens than their parents. The data provides an example for rational generation of novel peptidyl nucleoside antibiotics in an industrial producer.

  Streptomyces aureochromogenes YB172, Streptomyces tendae Tü901/8c, nikkomycin, antifungal antibiotics, chitinase inhibitors

  NCBI PubMed ID: 22465029
  Publication DOI: 10.1016/j.ymben.2012.03.006
  Journal NLM ID: 9815657
  Publisher: Brugge, Belgium; Orlando, FL: Academic Press
  Correspondence: Chen W ; Deng Z
  Institutions: State Key Laboratory of Microbial Metabolism, and School of Life Sciences & Biotechnology, Shanghai Jiao Tong University, Shanghai, China, Key Laboratory of Combinatorial Biosynthesis and Drug Discovery (Wuhan University), Ministry of Education, and Wuhan University School of Pharmaceutical Sciences, Wuhan, China
  Methods: 13C NMR, 1H NMR, NMR-2D, DNA techniques, MS/MS, extraction, cloning, ESI-QTOF-MS, antifungal activity test
  
   
  
  Streptomyces tendae Tü901/8c
  CSDB ID 45974 (all data & tools)

Show legend Show as text

Structure type: monomer ; 478.1415 [M+H]+
Trivial name: polyoxin N
Compound class: glycoside

• Article ID: 5368
  Zhai L, Lin S, Qu D, Hong X, Bai L, Chen W, Deng Z "Engineering of an industrial polyoxin producer for the rational production of hybrid peptidyl nucleoside antibiotics" - Metabolic Engineering 14(4) (2012) 388-393
  

  Polyoxins and nikkomycins are potent antifungal peptidyl nucleoside antibiotics, which inhibit fungal cell wall biosynthesis. They consist of a nucleoside core and one or two independent peptidyl moieties attached to the core at different sites. Making mutations and introducing heterologous genes into an industrial Streptomyces aureochromogenes polyoxin producer, resulted in the production of four polyoxin-nikkomycin hybrid antibiotics designated as polyoxin N and nikkoxin B-D, whose structures were confirmed using high resolution MS and NMR. Two of the hybrid antibiotics, polyoxin N and nikkoxin D, were significantly more potent against some human or plant fungal pathogens than their parents. The data provides an example for rational generation of novel peptidyl nucleoside antibiotics in an industrial producer.

  Streptomyces aureochromogenes YB172, Streptomyces tendae Tü901/8c, nikkomycin, antifungal antibiotics, chitinase inhibitors

  NCBI PubMed ID: 22465029
  Publication DOI: 10.1016/j.ymben.2012.03.006
  Journal NLM ID: 9815657
  Publisher: Brugge, Belgium; Orlando, FL: Academic Press
  Correspondence: Chen W ; Deng Z
  Institutions: State Key Laboratory of Microbial Metabolism, and School of Life Sciences & Biotechnology, Shanghai Jiao Tong University, Shanghai, China, Key Laboratory of Combinatorial Biosynthesis and Drug Discovery (Wuhan University), Ministry of Education, and Wuhan University School of Pharmaceutical Sciences, Wuhan, China
  Methods: 13C NMR, 1H NMR, NMR-2D, DNA techniques, MS/MS, extraction, cloning, ESI-QTOF-MS, antifungal activity test
  
   
  
  Streptomyces aureochromogenes ZLP3 SA2 (attB::pJTU5701 ΔnikB mutant), Streptomyces aureochromogenes ZLP2 SA2 (attB::pJTU5701 ΔnikB mutant)
  CSDB ID 45975 (all data & tools)

Show legend Show as text

Structure type: monomer ; 607.1843 [M+H]+
Trivial name: nikkomycin B
Compound class: glycoside

• Article ID: 5368
  Zhai L, Lin S, Qu D, Hong X, Bai L, Chen W, Deng Z "Engineering of an industrial polyoxin producer for the rational production of hybrid peptidyl nucleoside antibiotics" - Metabolic Engineering 14(4) (2012) 388-393
  

  Polyoxins and nikkomycins are potent antifungal peptidyl nucleoside antibiotics, which inhibit fungal cell wall biosynthesis. They consist of a nucleoside core and one or two independent peptidyl moieties attached to the core at different sites. Making mutations and introducing heterologous genes into an industrial Streptomyces aureochromogenes polyoxin producer, resulted in the production of four polyoxin-nikkomycin hybrid antibiotics designated as polyoxin N and nikkoxin B-D, whose structures were confirmed using high resolution MS and NMR. Two of the hybrid antibiotics, polyoxin N and nikkoxin D, were significantly more potent against some human or plant fungal pathogens than their parents. The data provides an example for rational generation of novel peptidyl nucleoside antibiotics in an industrial producer.

  Streptomyces aureochromogenes YB172, Streptomyces tendae Tü901/8c, nikkomycin, antifungal antibiotics, chitinase inhibitors

  NCBI PubMed ID: 22465029
  Publication DOI: 10.1016/j.ymben.2012.03.006
  Journal NLM ID: 9815657
  Publisher: Brugge, Belgium; Orlando, FL: Academic Press
  Correspondence: Chen W ; Deng Z
  Institutions: State Key Laboratory of Microbial Metabolism, and School of Life Sciences & Biotechnology, Shanghai Jiao Tong University, Shanghai, China, Key Laboratory of Combinatorial Biosynthesis and Drug Discovery (Wuhan University), Ministry of Education, and Wuhan University School of Pharmaceutical Sciences, Wuhan, China
  Methods: 13C NMR, 1H NMR, NMR-2D, DNA techniques, MS/MS, extraction, cloning, ESI-QTOF-MS, antifungal activity test
  
   
  
  Streptomyces aureochromogenes ZLP3 SA2 (attB::pJTU5701 ΔnikB mutant), Streptomyces aureochromogenes ZLP2 SA2 (attB::pJTU5701 ΔnikB mutant)
  CSDB ID 45976 (all data & tools)

Show legend Show as text

Structure type: monomer ; 607.1847 [M+H]+
Trivial name: nikkomycin C
Compound class: glycoside

• Article ID: 5368
  Zhai L, Lin S, Qu D, Hong X, Bai L, Chen W, Deng Z "Engineering of an industrial polyoxin producer for the rational production of hybrid peptidyl nucleoside antibiotics" - Metabolic Engineering 14(4) (2012) 388-393
  

  Polyoxins and nikkomycins are potent antifungal peptidyl nucleoside antibiotics, which inhibit fungal cell wall biosynthesis. They consist of a nucleoside core and one or two independent peptidyl moieties attached to the core at different sites. Making mutations and introducing heterologous genes into an industrial Streptomyces aureochromogenes polyoxin producer, resulted in the production of four polyoxin-nikkomycin hybrid antibiotics designated as polyoxin N and nikkoxin B-D, whose structures were confirmed using high resolution MS and NMR. Two of the hybrid antibiotics, polyoxin N and nikkoxin D, were significantly more potent against some human or plant fungal pathogens than their parents. The data provides an example for rational generation of novel peptidyl nucleoside antibiotics in an industrial producer.

  Streptomyces aureochromogenes YB172, Streptomyces tendae Tü901/8c, nikkomycin, antifungal antibiotics, chitinase inhibitors

  NCBI PubMed ID: 22465029
  Publication DOI: 10.1016/j.ymben.2012.03.006
  Journal NLM ID: 9815657
  Publisher: Brugge, Belgium; Orlando, FL: Academic Press
  Correspondence: Chen W ; Deng Z
  Institutions: State Key Laboratory of Microbial Metabolism, and School of Life Sciences & Biotechnology, Shanghai Jiao Tong University, Shanghai, China, Key Laboratory of Combinatorial Biosynthesis and Drug Discovery (Wuhan University), Ministry of Education, and Wuhan University School of Pharmaceutical Sciences, Wuhan, China
  Methods: 13C NMR, 1H NMR, NMR-2D, DNA techniques, MS/MS, extraction, cloning, ESI-QTOF-MS, antifungal activity test
  
   
  
  Streptomyces aureochromogenes ZLP6 SA2 (attB::pJTU5701 ΔnikBΔnikQ mutant)
  CSDB ID 45977 (all data & tools)

Show legend Show as text

Structure type: monomer ; 587.1946 [M+H]+
Trivial name: nikkomycin D
Compound class: glycoside

• Article ID: 5368
  Zhai L, Lin S, Qu D, Hong X, Bai L, Chen W, Deng Z "Engineering of an industrial polyoxin producer for the rational production of hybrid peptidyl nucleoside antibiotics" - Metabolic Engineering 14(4) (2012) 388-393
  

  Polyoxins and nikkomycins are potent antifungal peptidyl nucleoside antibiotics, which inhibit fungal cell wall biosynthesis. They consist of a nucleoside core and one or two independent peptidyl moieties attached to the core at different sites. Making mutations and introducing heterologous genes into an industrial Streptomyces aureochromogenes polyoxin producer, resulted in the production of four polyoxin-nikkomycin hybrid antibiotics designated as polyoxin N and nikkoxin B-D, whose structures were confirmed using high resolution MS and NMR. Two of the hybrid antibiotics, polyoxin N and nikkoxin D, were significantly more potent against some human or plant fungal pathogens than their parents. The data provides an example for rational generation of novel peptidyl nucleoside antibiotics in an industrial producer.

  Streptomyces aureochromogenes YB172, Streptomyces tendae Tü901/8c, nikkomycin, antifungal antibiotics, chitinase inhibitors

  NCBI PubMed ID: 22465029
  Publication DOI: 10.1016/j.ymben.2012.03.006
  Journal NLM ID: 9815657
  Publisher: Brugge, Belgium; Orlando, FL: Academic Press
  Correspondence: Chen W ; Deng Z
  Institutions: State Key Laboratory of Microbial Metabolism, and School of Life Sciences & Biotechnology, Shanghai Jiao Tong University, Shanghai, China, Key Laboratory of Combinatorial Biosynthesis and Drug Discovery (Wuhan University), Ministry of Education, and Wuhan University School of Pharmaceutical Sciences, Wuhan, China
  Methods: 13C NMR, 1H NMR, NMR-2D, DNA techniques, MS/MS, extraction, cloning, ESI-QTOF-MS, antifungal activity test
  
   
  
  Streptomyces aureochromogenes ZLP2 SA2 (attB::pJTU5701 ΔnikB mutant)
  CSDB ID 45978 (all data & tools)

Show legend Show as text

Structure type: monomer
C₁₆H₂₃N₅O₁₂
Trivial name: polyoxin N
Compound class: glycoside

• Article ID: 5377
  Uramoto M, Matsuoka M, Liehr JG, McCloskey JA, Isono K "Polyoxin N, a new member of the polyoxin family" - Agricultural and Biological Chemistry 45(8) (1981) 1901-1902
  

  Polyoxins A-M have been isolated from the culture filtrate of Streptomyces cacaoi var. asoensis. More recently, a newly isolated soil streptomycete designated as Streptomyces piomogenus was found to produce polyoxins L and M. In addition, this strain has been found to produce a minor component, polyoxin N.

  antibiotic, polyoxin, Streptomyces cacaoi var. asoensis

  Publication DOI: 10.1080/00021369.1981.10864808
  Journal NLM ID: 0370452
  Publisher: Tokyo: Agricultural Chemical Society Of Japan
  Institutions: The Institute of Physical and Chemical Research, Wako-shi, Japan, Central Research Laboratories, Hokko Chemical Industry Co. Ltd., Atsugi-shi, Japan, Institute for Lipid Research and Department of Biochemistry, Baylor College of Medicine, Houston, USA
  Methods: 13C NMR, 1H NMR, acid hydrolysis, MS, UV, enzymatic digestion, optical rotation measurement, CC, cell growth, melting point determination, evaporation, antifungal activity test
  
   
  
  Streptomyces piomogenus
  CSDB ID 46024 (all data & tools)

Show legend Show as text

Structure type: monomer
C₁₀H₁₃N₃O₇
Compound class: glycoside

• Article ID: 5377
  Uramoto M, Matsuoka M, Liehr JG, McCloskey JA, Isono K "Polyoxin N, a new member of the polyoxin family" - Agricultural and Biological Chemistry 45(8) (1981) 1901-1902
  

  Polyoxins A-M have been isolated from the culture filtrate of Streptomyces cacaoi var. asoensis. More recently, a newly isolated soil streptomycete designated as Streptomyces piomogenus was found to produce polyoxins L and M. In addition, this strain has been found to produce a minor component, polyoxin N.

  antibiotic, polyoxin, Streptomyces cacaoi var. asoensis

  Publication DOI: 10.1080/00021369.1981.10864808
  Journal NLM ID: 0370452
  Publisher: Tokyo: Agricultural Chemical Society Of Japan
  Institutions: The Institute of Physical and Chemical Research, Wako-shi, Japan, Central Research Laboratories, Hokko Chemical Industry Co. Ltd., Atsugi-shi, Japan, Institute for Lipid Research and Department of Biochemistry, Baylor College of Medicine, Houston, USA
  Methods: 13C NMR, 1H NMR, acid hydrolysis, MS, UV, enzymatic digestion, optical rotation measurement, CC, cell growth, melting point determination, evaporation, antifungal activity test
  
   
  
  Streptomyces piomogenus
  CSDB ID 46025 (all data & tools)

Show legend Show as text

Structure type: monomer ; 464.2 [M+H]+
Trivial name: nikkomycin Z
Compound class: glycoside

• Article ID: 5382
  Feng C, Ling H, Du D, Zhang J, Niu G, Tan H "Novel nikkomycin analogues generated by mutasynthesis in Streptomyces ansochromogenes" - Microbial Cell Factories 13(1) (2014) 1-10
  

  Nikkomycins are competitive inhibitors of chitin synthase and inhibit the growth of filamentous fungi, insects, acarids and yeasts. The gene cluster responsible for biosynthesis of nikkomycins has been cloned and the biosynthetic pathway was elucidated at the genetic, enzymatic and regulatory levels. Streptomyces ansochromogenes ΔsanL was constructed by homologous recombination and the mutant strain was fed with benzoic acid, 4-hydroxybenzoic acid, nicotinic acid and isonicotinic acid. Two novel nikkomycin analogues were produced when cultures were supplemented with nicotinic acid. These two compounds were identified as nikkomycin Px and Pz by electrospray ionization mass spectrometry (ESI-MS) and nuclear magnetic resonance (NMR). Bioassays against Candida albicans and Alternaria longipes showed that nikkomycin Px and Pz exhibited comparatively strong inhibitory activity as nikkomycin X and Z produced by Streptomyces ansochromogenes 7100 (wild-type strain). Moreover, nikkomycin Px and Pz were found to be more stable than nikkomycin X and Z at different pH and temperature conditions. Two novel nikkomycin analogues (nikkomycin Px and Pz) were generated by mutasynthesis with the sanL inactivated mutant of Streptomyces ansochromogenes 7100. Although antifungal activities of these two compounds are similar to those of nikkomycin X and Z, their stabilities are much better than nikkomycin X and Z under different pHs and temperatures.

  novel analogues, mutasynthesis, sanL mutant, Streptomyces ansochromogenes

  NCBI PubMed ID: 24751325
  Publication DOI: 10.1186/1475-2859-13-59
  Journal NLM ID: 101139812
  Publisher: London: BioMed Central
  Correspondence: Niu G
  Institutions: State Key Laboratory of Microbial Resources, Institute of Microbiology, Chinese Academy of Sciences, Beijing, China, University of Chinese Academy of Sciences, Beijing, China, Department of Molecular Oncology, H. Lee Moffitt Cancer Center and Research Institute, Tampa, USA
  Methods: 13C NMR, 1H NMR, ESI-MS, biological assays, HPLC, COSY, HSQC
  
   
  
  Streptomyces ansochromogenes, Streptomyces tendae
  CSDB ID 46406 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: nikkomycin X
Compound class: glycoside

• Article ID: 5382
  Feng C, Ling H, Du D, Zhang J, Niu G, Tan H "Novel nikkomycin analogues generated by mutasynthesis in Streptomyces ansochromogenes" - Microbial Cell Factories 13(1) (2014) 1-10
  

  Nikkomycins are competitive inhibitors of chitin synthase and inhibit the growth of filamentous fungi, insects, acarids and yeasts. The gene cluster responsible for biosynthesis of nikkomycins has been cloned and the biosynthetic pathway was elucidated at the genetic, enzymatic and regulatory levels. Streptomyces ansochromogenes ΔsanL was constructed by homologous recombination and the mutant strain was fed with benzoic acid, 4-hydroxybenzoic acid, nicotinic acid and isonicotinic acid. Two novel nikkomycin analogues were produced when cultures were supplemented with nicotinic acid. These two compounds were identified as nikkomycin Px and Pz by electrospray ionization mass spectrometry (ESI-MS) and nuclear magnetic resonance (NMR). Bioassays against Candida albicans and Alternaria longipes showed that nikkomycin Px and Pz exhibited comparatively strong inhibitory activity as nikkomycin X and Z produced by Streptomyces ansochromogenes 7100 (wild-type strain). Moreover, nikkomycin Px and Pz were found to be more stable than nikkomycin X and Z at different pH and temperature conditions. Two novel nikkomycin analogues (nikkomycin Px and Pz) were generated by mutasynthesis with the sanL inactivated mutant of Streptomyces ansochromogenes 7100. Although antifungal activities of these two compounds are similar to those of nikkomycin X and Z, their stabilities are much better than nikkomycin X and Z under different pHs and temperatures.

  novel analogues, mutasynthesis, sanL mutant, Streptomyces ansochromogenes

  NCBI PubMed ID: 24751325
  Publication DOI: 10.1186/1475-2859-13-59
  Journal NLM ID: 101139812
  Publisher: London: BioMed Central
  Correspondence: Niu G
  Institutions: State Key Laboratory of Microbial Resources, Institute of Microbiology, Chinese Academy of Sciences, Beijing, China, University of Chinese Academy of Sciences, Beijing, China, Department of Molecular Oncology, H. Lee Moffitt Cancer Center and Research Institute, Tampa, USA
  Methods: 13C NMR, 1H NMR, ESI-MS, biological assays, HPLC, COSY, HSQC
  
   
  
  Streptomyces ansochromogenes, Streptomyces tendae
  CSDB ID 46407 (all data & tools)

Show legend Show as text

Structure type: monomer ; 480.2 [M+H]+
Trivial name: nikkomycin Pz
Compound class: glycoside

• Article ID: 5382
  Feng C, Ling H, Du D, Zhang J, Niu G, Tan H "Novel nikkomycin analogues generated by mutasynthesis in Streptomyces ansochromogenes" - Microbial Cell Factories 13(1) (2014) 1-10
  

  Nikkomycins are competitive inhibitors of chitin synthase and inhibit the growth of filamentous fungi, insects, acarids and yeasts. The gene cluster responsible for biosynthesis of nikkomycins has been cloned and the biosynthetic pathway was elucidated at the genetic, enzymatic and regulatory levels. Streptomyces ansochromogenes ΔsanL was constructed by homologous recombination and the mutant strain was fed with benzoic acid, 4-hydroxybenzoic acid, nicotinic acid and isonicotinic acid. Two novel nikkomycin analogues were produced when cultures were supplemented with nicotinic acid. These two compounds were identified as nikkomycin Px and Pz by electrospray ionization mass spectrometry (ESI-MS) and nuclear magnetic resonance (NMR). Bioassays against Candida albicans and Alternaria longipes showed that nikkomycin Px and Pz exhibited comparatively strong inhibitory activity as nikkomycin X and Z produced by Streptomyces ansochromogenes 7100 (wild-type strain). Moreover, nikkomycin Px and Pz were found to be more stable than nikkomycin X and Z at different pH and temperature conditions. Two novel nikkomycin analogues (nikkomycin Px and Pz) were generated by mutasynthesis with the sanL inactivated mutant of Streptomyces ansochromogenes 7100. Although antifungal activities of these two compounds are similar to those of nikkomycin X and Z, their stabilities are much better than nikkomycin X and Z under different pHs and temperatures.

  novel analogues, mutasynthesis, sanL mutant, Streptomyces ansochromogenes

  NCBI PubMed ID: 24751325
  Publication DOI: 10.1186/1475-2859-13-59
  Journal NLM ID: 101139812
  Publisher: London: BioMed Central
  Correspondence: Niu G
  Institutions: State Key Laboratory of Microbial Resources, Institute of Microbiology, Chinese Academy of Sciences, Beijing, China, University of Chinese Academy of Sciences, Beijing, China, Department of Molecular Oncology, H. Lee Moffitt Cancer Center and Research Institute, Tampa, USA
  Methods: 13C NMR, 1H NMR, ESI-MS, biological assays, HPLC, COSY, HSQC
  
   
  
  Streptomyces ansochromogenes 7100
  CSDB ID 46408 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: nikkomycin Px
Compound class: glycoside

• Article ID: 5382
  Feng C, Ling H, Du D, Zhang J, Niu G, Tan H "Novel nikkomycin analogues generated by mutasynthesis in Streptomyces ansochromogenes" - Microbial Cell Factories 13(1) (2014) 1-10
  

  Nikkomycins are competitive inhibitors of chitin synthase and inhibit the growth of filamentous fungi, insects, acarids and yeasts. The gene cluster responsible for biosynthesis of nikkomycins has been cloned and the biosynthetic pathway was elucidated at the genetic, enzymatic and regulatory levels. Streptomyces ansochromogenes ΔsanL was constructed by homologous recombination and the mutant strain was fed with benzoic acid, 4-hydroxybenzoic acid, nicotinic acid and isonicotinic acid. Two novel nikkomycin analogues were produced when cultures were supplemented with nicotinic acid. These two compounds were identified as nikkomycin Px and Pz by electrospray ionization mass spectrometry (ESI-MS) and nuclear magnetic resonance (NMR). Bioassays against Candida albicans and Alternaria longipes showed that nikkomycin Px and Pz exhibited comparatively strong inhibitory activity as nikkomycin X and Z produced by Streptomyces ansochromogenes 7100 (wild-type strain). Moreover, nikkomycin Px and Pz were found to be more stable than nikkomycin X and Z at different pH and temperature conditions. Two novel nikkomycin analogues (nikkomycin Px and Pz) were generated by mutasynthesis with the sanL inactivated mutant of Streptomyces ansochromogenes 7100. Although antifungal activities of these two compounds are similar to those of nikkomycin X and Z, their stabilities are much better than nikkomycin X and Z under different pHs and temperatures.

  novel analogues, mutasynthesis, sanL mutant, Streptomyces ansochromogenes

  NCBI PubMed ID: 24751325
  Publication DOI: 10.1186/1475-2859-13-59
  Journal NLM ID: 101139812
  Publisher: London: BioMed Central
  Correspondence: Niu G
  Institutions: State Key Laboratory of Microbial Resources, Institute of Microbiology, Chinese Academy of Sciences, Beijing, China, University of Chinese Academy of Sciences, Beijing, China, Department of Molecular Oncology, H. Lee Moffitt Cancer Center and Research Institute, Tampa, USA
  Methods: 13C NMR, 1H NMR, ESI-MS, biological assays, HPLC, COSY, HSQC
  
   
  
  Streptomyces ansochromogenes 7100
  CSDB ID 46409 (all data & tools)

Show legend Show as text

Structure type: monomer ; 449 [M-H]-
Trivial name: nikkomycin Wx
Compound class: glycoside

• Article ID: 5550
  Decker H, Walz F, Bormann C, Zähner H, Fiedler HP, Heitsch H, Konig WA "Metabolic products of microorganisms. 255. Nikkomycins Wz and Wx, new chitin synthetase inhibitors from Streptomyces tendae" - The Journal of Antibiotics 43(1) (1990) 43-48
  

  Two new dipeptidyl nikkomycins of the Z and X type were isolated from the culture broth of Streptomyces tendae TÜ 901/395-11/32 and characterized. They show a variation in the amino acid moiety of the molecule. Nikkomycin Wz is composed of L-tyrosine and 5-amino-5-deoxy-D-allo-furanuronic acid N-glycosidally bound to uracil, whereas nikkomycin Wx is composed of L-tyrosine and 5-amino-5-deoxy-D-allo-furanuronic acid N-glycosidally bound to 4-formyl-4-imidazolin-2-one. The new nikkomycins are good inhibitors of chitin synthetase from Coprinus cinereus but they did not inhibit growth of fungi and yeasts

  antibiotics, nikkomycins, Streptomyces tendae

  NCBI PubMed ID: 2137814
  Publication DOI: 10.7164/antibiotics.43.43
  Journal NLM ID: 0151115
  Publisher: London: Nature Publishing Group
  Institutions: Biologisches Institut, LB Mikrobiologie/Antibiotika, Universität Tübingen, Tübingen, Germany, Institut für Organische Chemie, Universität Hamburg, Hamburg, Germany
  Methods: 1H NMR, methylation, FAB-MS, GC-MS, acid hydrolysis, biological assays, HPLC, extraction, acetylation, CC, cell growth, mutagenesis, enzymatic assay
  
   
  
  Streptomyces tendae TÜ 901/395-11/32
  CSDB ID 47270 (all data & tools)

Show legend Show as text

Structure type: monomer ; 449 [M-H]-
Trivial name: nikkomycin Wz
Compound class: glycoside

• Article ID: 5550
  Decker H, Walz F, Bormann C, Zähner H, Fiedler HP, Heitsch H, Konig WA "Metabolic products of microorganisms. 255. Nikkomycins Wz and Wx, new chitin synthetase inhibitors from Streptomyces tendae" - The Journal of Antibiotics 43(1) (1990) 43-48
  

  Two new dipeptidyl nikkomycins of the Z and X type were isolated from the culture broth of Streptomyces tendae TÜ 901/395-11/32 and characterized. They show a variation in the amino acid moiety of the molecule. Nikkomycin Wz is composed of L-tyrosine and 5-amino-5-deoxy-D-allo-furanuronic acid N-glycosidally bound to uracil, whereas nikkomycin Wx is composed of L-tyrosine and 5-amino-5-deoxy-D-allo-furanuronic acid N-glycosidally bound to 4-formyl-4-imidazolin-2-one. The new nikkomycins are good inhibitors of chitin synthetase from Coprinus cinereus but they did not inhibit growth of fungi and yeasts

  antibiotics, nikkomycins, Streptomyces tendae

  NCBI PubMed ID: 2137814
  Publication DOI: 10.7164/antibiotics.43.43
  Journal NLM ID: 0151115
  Publisher: London: Nature Publishing Group
  Institutions: Biologisches Institut, LB Mikrobiologie/Antibiotika, Universität Tübingen, Tübingen, Germany, Institut für Organische Chemie, Universität Hamburg, Hamburg, Germany
  Methods: 1H NMR, methylation, FAB-MS, GC-MS, acid hydrolysis, biological assays, HPLC, extraction, acetylation, CC, cell growth, mutagenesis, enzymatic assay
  
   
  
  Streptomyces tendae TÜ 901/395-11/32
  CSDB ID 47271 (all data & tools)