Guadinomines, Type III Secretion System Inhibitors, Produced by Streptomyces sp. K01-0509 (original) (raw)

II. Physico-chemical Properties and Structure Elucidation

The Journal of Antibiotics volume 61, pages 230–236 (2008) Cite this article

Abstract

The structures of guadinomines, new inhibitors of a bacterial Type III secretion system produced by Streptomyces sp. K01-0509, were elucidated by spectroscopic studies including various NMR experiments. Guadinomines A, B, C1, C2 and D consist of a carbamoylated cyclic guanidinyl moiety, an alkyl chain moiety and an L-Ala-L-Val moiety in common, while guadinomic acid is a smaller molecule consisting of a carbamoylated cyclic guanidinyl moiety and a hydroxyl hexanoate moiety.

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References

  1. Abe A . Development of the screening system for the bacterial type III secretion apparatus inhibitor. Jpn J Antibiot 55: 331–336 ( 2002)
    CAS PubMed Google Scholar
  2. Iwatsuki M, Uchida R, Yoshijima H, Ui H, Shiomi K, Matsumoto A, Takahashi Y, Abe A, Tomoda H, Ōmura S . Guadinomines, Type III secretion system inhibitors, produced by Streptomyces sp. K01-0509. I. Taxonomy, fermentation, isolation and biological properties. J Antibiot 61: 222–229 ( 2008)
    Article CAS PubMed Google Scholar
  3. Iwatsuki M, Tomoda H, Uchida R, Gouda H, Hirono S, Ōmura S . Lariatins, antimycobacterial peptides produced by Rhodococcus sp. K01-B0171, have a lasso structure. J Am Chem Soc 128: 7486–7491 ( 2006)
    Article CAS Google Scholar
  4. Technical bulletin (3), Selection of SUMICHIRAL OA columns : Sumika Chemical Analysis service, Ltd. Scientific instruments Div. chromatography group
  5. List PH . Sodium pentacyanoamineferrate (II) for urea, thiourea and guanidines. Hoppe-seylers Z. Physiol Chem 305: 27 ( 1956)
  6. Tsuchiya S, Sunazuka T, Hirose T, Mori R, Tanaka T, Iwatsuki M, Ōmura S . Asymmetric total synthesis of (+)-K01-0509 B: Determination of absolute configuration. Org Lett 24: 5577–5580 ( 2006)
    Article Google Scholar
  7. Kuwahara A, Nishikiori T, Shimada N, Nakagawa T, Fukazawa H, Mizuno S, Uehara Y . NA22598A1, a novel antitumor substance produced by Streptomyces sp. NA22598. J Antibiot 50: 712–713 ( 1997)
    Article CAS PubMed Google Scholar
  8. Horii S, Kameda Y . Enduracidin, a new antibiotc. V. Structures of new basic amino acids, enduracididine and alloenduracididine. J Antibiot 11: 665–667 ( 1968)
    Article Google Scholar
  9. Singh MP, Petersen PJ, Weiss WJ, Janso JE, Luckman SW, Lenoy EB, Bradford PA, Testa RT, Greenstein M . Mannopeptimycins, new cyclic glycopeptide antibiotics produced by Streptomyces hygroscopicus LL-AC98: Antibacterial and mechanistic activities. Antimicrob Agents Chemother 47: 62–69 ( 2003)
    Article CAS PubMed PubMed Central Google Scholar
  10. Fellows LE, Hider RC, Bell EA . 3-[2-amino-2 imidazolin-4(5)-yl]alanine (enduracididine) and 2-[2-amino-2-imidazolin-4(5)-yl]acetic acid in seeds of Lonchocarpus sericeus. Phytochemistry 16: 1957–1959 ( 1977)
    Article CAS Google Scholar
  11. Matsunaga S, Moore RE, Niemczura WP, Carmichael WP . Anatoxin-a(s), a potent anticholinesterase from Anabaena flos-aquae. J Am Chem Soc 111: 8021–8023 ( 1989)
    Article CAS Google Scholar

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Author notes

  1. Ryuji Uchida & Tomoyasu Hirose
    Present address: School of Pharmacy, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan

Authors and Affiliations

  1. The Kitasato Institute, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8642, Japan
    Masato Iwatsuki, Ryuji Uchida, Yong-Pil Kim, Tomoyasu Hirose & Satoshi Ōmura
  2. Kitasato Institute for Life Sciences and Graduate School of Infection Control Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan
    Hitomi Yoshijima, Hideaki Ui, Kazuro Shiomi, Toshiaki Sunazuka, Akio Abe & Hiroshi Tomoda

Authors

  1. Masato Iwatsuki
  2. Ryuji Uchida
  3. Hitomi Yoshijima
  4. Hideaki Ui
  5. Kazuro Shiomi
  6. Yong-Pil Kim
  7. Tomoyasu Hirose
  8. Toshiaki Sunazuka
  9. Akio Abe
  10. Hiroshi Tomoda
  11. Satoshi Ōmura

Corresponding authors

Correspondence toHiroshi Tomoda or Satoshi Ōmura.

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Iwatsuki, M., Uchida, R., Yoshijima, H. et al. Guadinomines, Type III Secretion System Inhibitors, Produced by Streptomyces sp. K01-0509.J Antibiot 61, 230–236 (2008). https://doi.org/10.1038/ja.2008.33

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