| Identification | Back Directory | [Name]
ascamycin | [CAS]
91432-48-3 | [Synonyms]
ascamycin
2-Chloro-5'-O-[(L-alanylamino)sulfonyl]adenosine
2-Chloro-5'-O-[[(S)-2-amino-1-oxopropyl]sulfamoyl]adenosine
(+)-5'-O-[[(S)-2-Amino-1-oxopropyl]aminosulfonyl]-2-chloroadenosine | [MDL Number]
MFCD09838109 | [MOL File]
91432-48-3.mol |
| Hazard Information | Back Directory | [Uses]
Ascamycin is a 5'-O-sulfonamide ribonucleoside antibiotic produced by Streptomyces sp. JCM9888. Ascamycin has a selective antibacterial activity against Xanthomonas species with MIC values of 0.4 μg/mL, 12.5 μg/mL and 12.5 μg/mL for Xanthomonas citri, Xanthomonas oryzae and Mycobacterium phlei, respectively[1][2][3]. | [Biological Activity]
Ascamycin is a 5'-O-sulfonamide ribonucleoside antibiotic produced by Streptomyces sp. JCM9888. It has selective antibacterial activity against Xanthomonas bacteria, with MIC values of 0.4 μg/mL, 12.5 μg/mL and 12.5 μg/mL for Xanthomonas citri, Xanthomonas oryzae and Mycobacterium phlei, respectively. | [in vitro]
The Ascamycin has C2-chloroadenine as the base on C-1' which lacks the chlorine. Ascamycin has a selective antibacterial activity against Xanthomonas species. When Ascamycin is dealanylated, Dealanylascamycin shows a broad antibacterial activity against various Gram-negative and Gram-positive bacteria. Xanthomonas citri is susceptible to Ascamycin by virtue of the Ascamycin-dealanylating enzyme on the cell surface. | [target]
MIC: 0.4 μg/mL ( Xanthomonas citri ), 12.5 μg/mL ( Xanthomonas oryzae ) and 12.5 μg/mL ( Mycobacterium phlei ) | [References]
[1] Isono K, et al. Ascamycin and dealanylascamycin, nucleoside antibiotics from Streptomyces sp. J Antibiot (Tokyo). 1984 Jun;37(6):670-2. DOI:10.7164/antibiotics.37.670
[2] Osada H, rt al. Purification and characterization of ascamycin-hydrolysing aminopeptidase from Xanthomonas citri. Biochem J. 1986 Jan 15;233(2):459-63. DOI:10.1042/bj2330459
[3] Zhao C, et al. Characterization of biosynthetic genes of ascamycin/dealanylascamycin featuring a 5'-O-sulfonamide moiety in Streptomyces sp. JCM9888. PLoS One. 2014 Dec 5;9(12):e114722. DOI:10.1371/journal.pone.0114722 |
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