91432-48-3

91432-48-3 structure

Name: Ascamycin
Chemical Name: 2-chloro-5'-O-(N-(L-alanyl)sulfamoyl)adenosine (Ascamycin)
CAS Number: 91432-48-3
Molecular Formula: C₁₃H₁₈ClN₇O₇S
Molecular Weight: 451.84300
Catalog: Signaling Pathways Anti-infection Bacterial
Create Date: 2018-01-04 02:52:50
Modify Date: 2024-01-11 12:31:54
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].

Name	2-chloro-5'-O-(N-(L-alanyl)sulfamoyl)adenosine (Ascamycin)
Synonyms	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

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.

Molecular Formula	C₁₃H₁₈ClN₇O₇S
Molecular Weight	451.84300
Exact Mass	451.06800
PSA	226.18000
LogP	0.15910

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