Ascamycin

Names

[ Name ]:
Ascamycin

[Synonym ]:
ascamycin
2-chloro-5'-O-[N-(L-alanyl)sulfamoyl]adenosine (Ascamycin)
((S)-2-Amino-propionyl)-sulfamic acid (2R,3S,4R,5R)-5-(6-amino-2-chloro-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester

Biological Activity

[Description]:

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].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog

Signaling Pathways >> Anti-infection >> Bacterial

[Target]

MIC: 0.4 μg/mL (Xanthomonas citri), 12.5 μg/mL (Xanthomonas oryzae) and 12.5 μg/mL (Mycobacterium phlei)[1]

[In Vitro]

The Ascamycin has C2-chloroadenine as the base on C-1' which lacks the chlorine[1]. 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[2].

[References]

[1]. Isono K, et al. Ascamycin and dealanylascamycin, nucleoside antibiotics from Streptomyces sp. J Antibiot (Tokyo). 1984 Jun;37(6):670-2.

[2]. Osada H, rt al. Purification and characterization of ascamycin-hydrolysing aminopeptidase from Xanthomonas citri. Biochem J. 1986 Jan 15;233(2):459-63.

[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.

Chemical & Physical Properties

[ Molecular Formula ]:
C₁₃H₁₈ClN₇O₇S

[ Molecular Weight ]:
451.84300

[ Exact Mass ]:
451.06800

[ PSA ]:
226.18000

[ LogP ]:
0.15910