Ascamycin
- Structure
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- Producing organism
- Streptomyces sp.
- Biological activity
- antibacterial activity
- Abstract
- A newly isolated strain of Streptomyces sp. produces a new nucleoside antibiotic, ascamycin and the corresponding dealanyl derivative. The structure of ascamycin was determined to be 2-chloro-9-β-[5-O-(N-L-alanyl)sulfamoyl-D-ribofuranosyl]-adenine. Remarkable selective toxicity of ascamycin compared to the dealanyl derivative was accounted for on the basis of a dealanylating enzyme present in the envelope of sensitive bacteria. After dealanylation, it becomes permeable to cell membrane.
- References
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isolation and structural determination
- Isono K, Uramoto M, Osada H, Ubukata M, Kusakabe H, Koyama T, Miyata N, Sethi SK, McCloskey JA.: Structure and biological activity of ascamycin, a new nucleoside antibiotic.
Nucleic Acids Symp Ser, (15): 65-67 (1984)
- Isono K, Uramoto M, Kusakabe H, Miyata N, Koyama T, Ubukata M, Sethi SK, McCloskey JA.: Ascamycin and dealanylascamycin, nucleoside antibiotics from Streptomyces sp.
J Antibiot, 37(6): 670-672 (1984)synthesis- Ubukata M, Osada H, Isono K.: Synthesis and biological activity of nucleoside antibiotics, ascamycin and its amino acid analogs.
Nucleic Acids Symp Ser, (16): 81-83 (1985)biological activities- Osada H, Isono K.: Mechanism of action and selective toxicity of ascamycin, a nucleoside antibiotic.
Antimicrob Agents Chemother, 27(2): 230-233 (1985)- Osada H, Isono K.: Purification and characterization of ascamycin-hydrolysing aminopeptidase from Xanthomonas citri.
Biochem J, 233(2): 459-463 (1986)- Osada H, Isono K.: Occurrence of an ascamycin dealanylating enzyme, Xc-aminopeptidase, in mammalian cell membranes and susceptibility to ascamycin.
J Antibiot, 39(2): 286-293 (1986)- Sudo T, Shinohara K, Dohmae N, Takio K, Usami R, Horikoshi K, Osada H.: Isolation and characterization of the gene encoding an aminopeptidase involved in the selective toxicity of ascamycin toward Xanthomonas campestris pv. citri.
Biochem J, 319(Pt 1): 99-102 (1996) - Isono K, Uramoto M, Osada H, Ubukata M, Kusakabe H, Koyama T, Miyata N, Sethi SK, McCloskey JA.: Structure and biological activity of ascamycin, a new nucleoside antibiotic.