Abstract
Bacterial phospho-N-acetylmuramyl-pentapeptide translocase (translocase I: EC 2.7.8.13) is a key enzyme in peptidoglycan biosynthesis, and a known target of antibiotics. Here we report a new nucleoside inhibitor for translocase I, A-102395, isolated from the culture broth of the strain Amycolatopsis sp. SANK 60206. A-102395 is a new derivative of capuramycin that has the benzene with a uniquely substituted chain instead of an aminocaprolactam. A-102395 is a potent inhibitor of bacterial translocase I with IC50 value of 11 nM, but possesses no antimicrobial activity against various strains tested.
Similar content being viewed by others
Article PDF
References
Brandish PE, Kimura K, Inukai M, Southgate R, Lonsdale JT, Bugg TD . Modes of action of tunicamycin, liposidomycin B and mureidomycin A: Inhibition of phospho-N-acetylmuramyl-pentapeptide translocase from Escherichia coli. Antimicrob Agents Chemother 40: 1640–1644 ( 1996)
Inukai M, Isono F, Takahashi S, Enokita R, Sakaida Y, Haneishi T . Mureidomycin A∼D, novel peptidylnucleoside antibiotics with spheroplast forming activity. I. Taxonomy, fermentation, isolation and physico-chemical properties. J Antibiot 42: 662–666 ( 1989)
Karwowski JP, Jackson M, Theriault RJ, Chen RH, Barlow GJ, Maus ML . Pacidamycins, a novel series of antibiotics with anti-Pseudomonas aeruginosa activity. I. Taxonomy of the producing organism and fermentation. J Antibiot 42: 506–511 ( 1989)
Chatterjee S, Nadkarni SR, Vijayakumar EK, Patel MV, Ganguli BN, Fehlhaber HW, Vertesy L . Napsamycins, new Pseudomonas activity antibiotics of mureidomycin family from Streptomyces sp. HIL Y-82, 11372. J Antibiot 47: 595–598 ( 1994)
Ubukata M, Isono K . The structure of liposidomycin B, an inhibitor of bacterial peptidoglycan synthesis. J Am Chem Soc 110: 4416–4417 ( 1988)
Takatsuki A, Arima K, Tamura G . Tunicamycin, a new antibiotic. I. Isolation and characterization of tunicamycin. J Antibiot 24: 215–223 ( 1971)
Yamaguchi H, Sato S, Yoshida S, Takada K, Itou M, Seto H, Otake N . Capuramycin, a new nucleoside antibiotic. Taxonomy, fermentation, isolation and characterization. J Antibiot 39: 1047–1053 ( 1986)
Seto H, Otake N . The structure of a new nucleoside antibiotic, capuramycin. Tetrahedron Lett 29: 2343–2346 ( 1988)
Muramatsu Y, Muramatsu A, Ohnuki T, Ishi MM, Kizuka M, Enokita R, Tsutsumi S, Arai M, Ogawa Y, Suzuki T, Takatsu T, Inukai M . Studies on novel bacterial translocase I inhibitors. I. Taxonomy, fermentation, isolation, physico-chemical properties and structure elucidation of A-500359A, C, D and G. J Antibiot 56: 243–252 ( 2003)
Muramatsu Y, Ishii MM, Inukai M . Studies on novel bacterial translocase I inhibitors, A-500359s. II. Biological activities of A-500359 A, C, D and G. J Antibiot 56: 253–258 ( 2003)
Muramatsu Y, Miyakoshi S, Ogawa Y, Ohnuki T, Ishii MM, Arai M, Inukai M . Studies on novel bacterial translocase I inhibitors, A-500359s. III. Deaminocaprolactam derivaties of capuramycin: A-500359 E, F, H, M-1 and M-2. J Antibiot 56: 259–267 ( 2003)
Ohnuki T, Muramatsu Y, Miyakoshi S, Takatsu T, Inukai M . Studies on novel bacterial translocase I inhibitors, A-500359s. IV. Biosynthesis of A-500359s. J Antibiot 56: 268–279 ( 2003)
Muramatsu Y, Arai M, Sakaida Y, Takamatsu Y, Miyakoshi S, Inukai M . Studies on novel bacterial translocase I inhibitors, A-500359s. V. Enhanced production of capuramycin and A-500359A in Streptomyces griseus SANK 60196. J Antibiot 59: 601–606 ( 2006)
Mcdonald LA, Barbieri LR, Carter GT, Lenoy E, Lotvin J, Petersen PJ, Singh G, Williamson RT . Structures of the muraymycins, novel peptidoglycan biosynthesis inhibitors. J Am Chem Soc 124: 10260–10261 ( 2002)
Igarashi M, Nakagawa N, Doi N, Hattori S, Naganawa H, Hamada M . Caprazamycin B, a novel anti-tuberculosis antibiotic, from Streptomyces sp. J Antibiot 56: 580–583 ( 2003)
Igarashi M, Takahashi Y, Shibata T, Nakamura H, Naganawa H, Miyake T, Akamatsu Y . Caprazamycins, novel lipo-nucleoside antibiotics, from Streptomyces sp. II. Structure elucidation of caprazamycins. J Antibiot 58: 327–337 ( 2005)
Fernandes PB, Swanson RN, Hardy DJ, Hanson CW, Coen L, Rasmussen RR, Chen RH . Pacidamycins, a novel series of antibiotics with anti-Pseudomonas aeruginosa activity. III. Microbiologic profile. J Antibiot 42: 521–526 ( 1989)
Isono F, Kodama K, Inukai M . Susceptibility of Pseudomonas species to the novel antibiotics mureidomycins. Antimicrob Agents Chemother 36: 1024–1027 ( 1992)
Shirling EB, Gottlieb D . Methods for characterization of Streptomyces species. Int J Syst Bacteriol 16: 313–340 ( 1966)
Waksman SA . Classification, identification and description of genera and species. The Actinomycetes, Vol. 2. Williams & Wilkins, Baltimore, pp. 328–334 ( 1961)
Hasegawa T, Takizawa M, Tanida S . A rapid analysis for chemical grouping of aerobic actinomycetes. J Gen Appl Microbiol 29: 319–322 ( 1983)
Hecht ST, Causey WA . Rapid method for the detection and identification of mycolic acids in aerobic actinomycetes and related bacteria. J Clin Microbiol 4: 284–287 ( 1976)
Kay LE, Keifer P, Saarinen T . Pure absorption gradient enhanced heteronuclear single quantum correlation spectroscopy with improved sensitivity. J Am Chem Soc 114: 10663–10665 ( 1992)
Davis AL, Laue ED, Keeler J, Moskau D, Lohman J . Absorption-mode two-dimensional NMR spectra recorded using pulsed field gradients. J Magn Reson 94: 637–644 ( 1991)
Willker W, Leibfritz D, Kerssebaum R, Bermel W . Gradient selection in inverse heteronuclear correlation spectroscopy. Magn Reson Chem 31: 287–292 ( 1993)
Constantine GB, Remy CL, Johanne B, Nicole GV, Karin AS, Angela M, Suzanne C, Scott JH, Ving JL . Synthetic dihydropacidamycin antibiotics: A modified spectrum of activity for the pacidamycin class. Bioorg Med Chem Lett 13: 3305–3309 ( 2003)
Dini C, Didier-Laurent S, Drochon N, Feteanu S, Guillot JC, Monti F, Uridat E, Zhang J, Aszodi J . Synthesis of sub-micromolar inhibitors of MraY by exploring the region originally occupied by the diazepanone ring in the liposidomycin structure. Bioorg Med Chem Lett 12: 1209–1213 ( 2002)
Hotoda H, Furukawa M, Daigo M, Murayama K, Kaneko M, Muramatsu Y, Ishi MM, Miyakoshi S, Takatsu T, Inukai M, Kakuta M, Abe T, Harasaki T, Fukuoka T, Utsui Y, Ohya S . Synthesis and antimycobacterial activity of capuramycin analogues. Part 1: Substitution of the azepan-2-one moiety of capuramycin. Bioorg Med Chem Lett 13: 2829–2832 ( 2003)
Hotoda H, Daigo M, Furukawa M, Murayama K, Hasegawa AC, Kaneko M, Muramatsu Y, Ishi MM, Miyakoshi S, Takatsu T, Inukai M, Kakuta M, Abe T, Fukuoka T, Utsui Y, Ohya S . Synthesis and antimycobacterial activity of capuramycin analogues. Part 2: Acylated derivatives of capuramycin-related compounds. Bioorg Med Chem Lett 13: 2833–2836 ( 2003)
Miyake T, Takahashi Y, Igarashi M, Doi N, Shitara T, Sohtome H, Iijima K, Masuda T, Hattori S, Nakagawa N, Akamatsu Y . Novel semisynthetic antibiotics from caprazamycins (Part1): Caprazene derivatives and their anti-Mycobacterium tuberculosis activity. 43rd Interscience Conference on Antimicrobial Agents and Chemotherapy (ICAAC), Abstracts F-2140 ( 2003)
Miyake T, Shitara T, Igarashi M, Doi N, Takahashi Y, Sohtome H, Iijima K, Masuda T, Hattori S, Nakagawa N, Akamatsu Y . Novel semisynthetic antibiotics from caprazamycins (Part 2): Caprazol derivatives and their anti-Mycobacterium tuberculosis activity. 43rd Interscience Conference on Antimicrobial Agents and Chemotherapy (ICAAC), Abstracts F-2141 ( 2003)
Muramatsu Y, Ohnuki T, Ishi MM, Kizuka M, Enokita R, Miyakoshi S, Takatsu T, Inukai M . A-503083 A, B, E and F, Novel inhibitors of bacterial translocase I, produced by Streptomyces sp. SANK 62799. J Antibiot 57: 639–646 ( 2004)
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Murakami, R., Fujita, Y., Kizuka, M. et al. A-102395, a New Inhibitor of Bacterial Translocase I, Produced by Amycolatopsis sp. SANK 60206. J Antibiot 60, 690–695 (2007). https://doi.org/10.1038/ja.2007.88
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1038/ja.2007.88
Keywords
This article is cited by
-
Amycolatopsis alkalitolerans sp. nov., isolated from Gastrodia elata Blume
The Journal of Antibiotics (2020)
-
Liposidomycin, the first reported nucleoside antibiotic inhibitor of peptidoglycan biosynthesis translocase I: The discovery of liposidomycin and related compounds with a perspective on their application to new antibiotics
The Journal of Antibiotics (2019)
-
Muraminomicins, novel ester derivatives: in vitro and in vivo antistaphylococcal activity
The Journal of Antibiotics (2019)
-
Muraminomicins, new lipo-nucleoside antibiotics from Streptosporangium sp. SANK 60501-structure elucidations of muraminomicins and supply of the core component for derivatization
The Journal of Antibiotics (2019)
-
Novel semisynthetic antibiotics from caprazamycins A–G: caprazene derivatives and their antibacterial activity
The Journal of Antibiotics (2013)