Norplicacetin
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-02137 |
| CAS | |
| Molecular Weight | 503.55 |
| Molecular Formula | C24H33N5O7 |
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Description
It is originally isolated from Str. plicatus NCIB 11305. And it has the effect of anti-gram-positive bacteria and mycobacterium.
Specification
| IUPAC Name | 4-amino-N-[1-[(2R,5S,6R)-5-[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-(methylamino)oxan-2-yl]oxy-6-methyloxan-2-yl]-2-oxopyrimidin-4-yl]benzamide |
| Canonical SMILES | CC1C(CCC(O1)N2C=CC(=NC2=O)NC(=O)C3=CC=C(C=C3)N)OC4C(C(C(C(O4)C)NC)O)O |
| InChI | InChI=1S/C24H33N5O7/c1-12-16(36-23-21(31)20(30)19(26-3)13(2)35-23)8-9-18(34-12)29-11-10-17(28-24(29)33)27-22(32)14-4-6-15(25)7-5-14/h4-7,10-13,16,18-21,23,26,30-31H,8-9,25H2,1-3H3,(H,27,28,32,33)/t12-,13-,16+,18-,19-,20+,21-,23-/m1/s1 |
| InChI Key | HJFXGPLQIPLHSS-UOUGBBRZSA-N |
Properties
| Appearance | White Acicular Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycobacteria |
| Melting Point | 168-171°C |
Reference Reading
1. Characterization of the amicetin biosynthesis gene cluster from Streptomyces vinaceusdrappus NRRL 2363 implicates two alternative strategies for amide bond formation
Gaiyun Zhang, Haibo Zhang, Sumei Li, Ji Xiao, Guangtao Zhang, Yiguang Zhu, Siwen Niu, Jianhua Ju, Changsheng Zhang Appl Environ Microbiol. 2012 Apr;78(7):2393-401. doi: 10.1128/AEM.07185-11. Epub 2012 Jan 20.
Amicetin, an antibacterial and antiviral agent, belongs to a group of disaccharide nucleoside antibiotics featuring an α-(1→4)-glycoside bond in the disaccharide moiety. In this study, the amicetin biosynthesis gene cluster was cloned from Streptomyces vinaceusdrappus NRRL 2363 and localized on a 37-kb contiguous DNA region. Heterologous expression of the amicetin biosynthesis gene cluster in Streptomyces lividans TK64 resulted in the production of amicetin and its analogues, thereby confirming the identity of the ami gene cluster. In silico sequence analysis revealed that 21 genes were putatively involved in amicetin biosynthesis, including 3 for regulation and transportation, 10 for disaccharide biosynthesis, and 8 for the formation of the amicetin skeleton by the linkage of cytosine, p-aminobenzoic acid (PABA), and the terminal (+)-α-methylserine moieties. The inactivation of the benzoate coenzyme A (benzoate-CoA) ligase gene amiL and the N-acetyltransferase gene amiF led to two mutants that accumulated the same two compounds, cytosamine and 4-acetamido-3-hydroxybenzoic acid. These data indicated that AmiF functioned as an amide synthethase to link cytosine and PABA. The inactivation of amiR, encoding an acyl-CoA-acyl carrier protein transacylase, resulted in the production of plicacetin and norplicacetin, indicating AmiR to be responsible for attachment of the terminal methylserine moiety to form another amide bond. These findings implicated two alternative strategies for amide bond formation in amicetin biosynthesis.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
