17650-86-1 Usage
Enzyme inhibitor
These pyrimidine-containing glycoside antibiotic (FWAmicetin-A = 617.69 g/mol (free base); CAS 17650-86-1; FWAmicetin-B = 532.59 g/mol (free base)) from Streptomyces vinaceus-drappus and S. fasciculatus inhibits protein biosynthesis, exerting its bacteriostatic most potently on Grampositive bacteria. Amicetin B, also called plicacetin, was isolated from Streptomyces plicatus and has the identical structure minus the amethylseryl residue. It is weaker in action compared to amicetin A. Target(s): peptidyltransferase; peptidyl-tRNA hydrolase, or aminoacyl-tRNA hydrolase; ribonuclease P; protein biosynthesis.
Check Digit Verification of cas no
The CAS Registry Mumber 17650-86-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,7,6,5 and 0 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 17650-86:
(7*1)+(6*7)+(5*6)+(4*5)+(3*0)+(2*8)+(1*6)=121
121 % 10 = 1
So 17650-86-1 is a valid CAS Registry Number.
InChI:InChI=1/C29H42N6O9/c1-15-19(44-26-24(38)23(37)22(34(4)5)16(2)43-26)10-11-21(42-15)35-13-12-20(33-28(35)41)32-25(39)17-6-8-18(9-7-17)31-27(40)29(3,30)14-36/h6-9,12-13,15-16,19,21-24,26,36-38H,10-11,14,30H2,1-5H3,(H,31,40)(H,32,33,39,41)
17650-86-1Relevant articles and documents
Total Synthesis of Nucleoside Antibiotics Amicetin, Plicacetin, and Cytosaminomycin A—D
Fu, Jiqiang,Xu, Peng,Yu, Biao
, p. 2679 - 2684 (2021/08/03)
Amicetin and congeners constitute a small family of complex pyrimidine nucleosides, which exhibit strong antibiotic activities against Gram-positive bacteria and notably against strains of Mycobacterium tuberculosis. Herein, we report chemical synthesis of a series of disaccharide congeners of the amicetin family, including amicetin, plicacetin, and cytosaminomycin A—D. It is the first time for successful synthesis of amicetin, the prototypical member, and cytosaminomycins. The synthetic approach employs glycosyl N-phenyltrifluoroacetimidate and thioglycoside donors to construct the characteristic aminodeoxydisaccharides consisting of α-(1→4)-glycosidic linkage, uses gold(I)-catalyzed N-glycosylation to furnish 2-deoxy-β-nucleosides, and finally exploits amidation and global deprotection to complete the syntheses. It is noteworthy that the 3-O-protecting group in the 2-deoxydisaccharide donors is found to be crucial for a successful N-glycosylation to assemble the cytosaminomycin disaccharide nucleosides.
