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Cytosaminomycin A

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Category Antibiotics
Catalog number BBF-01140
CAS 157878-02-9
Molecular Weight 514.59
Molecular Formula C22H34N4O8S

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Fermentation Lab

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Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

It is produced by the strain of Streptomyces sp. KO-8119. It has anti-eimeria Tenella activity. The concentration of Cytosaminomycin A without cleavage in chicken embryo cells is 0.3-0.6 μg/mL.

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Synonyms N-[3-(Methylthio)acryloyl]-1-[4-O-[4-(dimethylamino)-4,6-dideoxy-alpha-D-glucopyranosyl]-2,6-dideoxy-beta-D-arabino-hexopyranosyl]cytosine
IUPAC Name (E)-N-[1-[(2R,4R,5S,6R)-5-[(2R,3R,4S,5S,6R)-5-(dimethylamino)-3,4-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]-2-oxopyrimidin-4-yl]-3-methylsulfanylprop-2-enamide
Canonical SMILES CC1C(C(C(C(O1)OC2C(OC(CC2O)N3C=CC(=NC3=O)NC(=O)C=CSC)C)O)O)N(C)C
InChI InChI=1S/C22H34N4O8S/c1-11-17(25(3)4)18(29)19(30)21(33-11)34-20-12(2)32-16(10-13(20)27)26-8-6-14(24-22(26)31)23-15(28)7-9-35-5/h6-9,11-13,16-21,27,29-30H,10H2,1-5H3,(H,23,24,28,31)/b9-7+/t11-,12-,13-,16-,17-,18+,19-,20-,21-/m1/s1
InChI Key OEIFFRHFKRNPAL-ZQEFWBPISA-N
Appearance Pale Yellow Powder
Density 1.47 g/cm3
Solubility Soluble in Methanol
1. Cytosaminomycins, new anticoccidial agents produced by Streptomyces sp. KO-8119. I. Taxonomy, production, isolation and physico-chemical and biological properties
K Haneda, M Shinose, A Seino, N Tabata, H Tomoda, Y Iwai, S Omura J Antibiot (Tokyo). 1994 Jul;47(7):774-81. doi: 10.7164/antibiotics.47.774.
Streptomyces amakusaensis KO-8119, a soil isolate, was found to produce a series of new anticoccidial compounds. Four active compounds, designated as cytosaminomycins A, B, C and D, were isolated from the fermentation broth of the producing strain by solvent extraction, silica gel column chromatography and preparative HPLC. Cytosaminomycins inhibited the growth of Eimeria tenella in an in vitro assay system using primary chicken embryonic cells as a host. No schizont in the cells was observed at concentrations ranging from 0.3 to 0.6 microgram/ml for cytosaminomycins A, B and C, and at 2.5 micrograms/ml for cytosaminomycin D.
2. Synthetic study of cytosaminomycins using the intramolecular glycosylation as a key step
Hideyuki Sugimura Nucleic Acids Res Suppl. 2003;(3):21-2. doi: 10.1093/nass/3.1.21.
2',6'-Dideoxy-beta-D-hexopyranosyl pyrimidine nucleoside, which is a component of anticoccidal antibiotics--cytosaminomycins, was synthesized in a stereoselective manner via the intramolecular pyrimidine delivery method. Further glycosylaion of the 4'-position with a glycosyl fluoride gave the disaccharide nucleoside skeleton of the cytosaminomycins.
3. Cytosaminomycins, new anticoccidial agents produced by Streptomyces sp. KO-8119. II. Structure elucidation of cytosaminomycins A, B, C and D
K Shiomi, K Haneda, H Tomoda, Y Iwai, S Omura J Antibiot (Tokyo). 1994 Jul;47(7):782-6. doi: 10.7164/antibiotics.47.782.
Structures of novel anticoccidial antibiotics, cytosaminomycins A, B, C and D, were elucidated by NMR studies. Cytosaminomycins were shown to be nucleoside antibiotics related to oxyplicacetin. Their carboxylic acid moieties bonded to the cytosine residue were different from that of oxyplicacetin. The carboxylic acids contained in cytosaminomycins A, B, C and D were (E)-3-(methylthio)acrylic acid, 4-methylaminobenzoic acid, 3-methylcrotonic acid, and tiglic acid, respectively.

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