Arginomycin
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| Category | Antibiotics |
| Catalog number | BBF-00079 |
| CAS | 106133-33-9 |
| Molecular Weight | 436.46 |
| Molecular Formula | C18H28N8O5 |
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Description
Arginomycin is a nucleoside antibiotic produced by Streptomyces arginensis. It has weak activity against Gram-positive bacteria and fungi.
Specification
| Synonyms | beta-D-erythro-Hex-2-enopyranuronic acid, 4-((2-amino-5-((aminoiminomethyl)methylamino)-3-methyl-1-oxopentyl)amino)-1-(4-amino-2-oxo-1(2H)-pyrimidinyl)-1,2,3,4-tetradeoxy-; 3-[[2-amino-5-[carbamimidoyl(methyl)amino]-3-methylpentanoyl]amino]-6-(4-amino-2-oxopyrimidin-1-yl)-3,6-dihydro-2H-pyran-2-carboxylic acid |
| IUPAC Name | 3-[[2-amino-5-[carbamimidoyl(methyl)amino]-3-methylpentanoyl]amino]-6-(4-amino-2-oxopyrimidin-1-yl)-3,6-dihydro-2H-pyran-2-carboxylic acid |
| Canonical SMILES | CC(CCN(C)C(=N)N)C(C(=O)NC1C=CC(OC1C(=O)O)N2C=CC(=NC2=O)N)N |
| InChI | InChI=1S/C18H28N8O5/c1-9(5-7-25(2)17(21)22)13(20)15(27)23-10-3-4-12(31-14(10)16(28)29)26-8-6-11(19)24-18(26)30/h3-4,6,8-10,12-14H,5,7,20H2,1-2H3,(H3,21,22)(H,23,27)(H,28,29)(H2,19,24,30) |
| InChI Key | QHXNKYPHTJBRJV-UHFFFAOYSA-N |
Properties
| Appearance | Solid |
| Antibiotic Activity Spectrum | Gram-positive bacteria; fungi |
| Melting Point | 218°C |
| Density | 1.57 g/cm3 |
Reference Reading
1. Biosynthesis of the β-methylarginine residue of peptidyl nucleoside arginomycin in Streptomyces arginensis NRRL 15941
Jun Feng, Jun Wu, Jie Gao, Zhigui Xia, Zixin Deng, Xinyi He Appl Environ Microbiol. 2014 Aug;80(16):5021-7. doi: 10.1128/AEM.01172-14. Epub 2014 Jun 6.
The peptidyl nucleoside arginomycin is active against Gram-positive bacteria and fungi but displays much lower toxicity to mice than its analog blasticidin S. It features a rare amino acid, β-methylarginine, which is attached to the deoxyhexose moiety via a 4'-aminoacyl bond. We here report cloning of the complete biosynthetic gene cluster for arginomycin from Streptomyces arginensis NRRL 15941. Among the 14 putative essential open reading frames, argM, encoding an aspartate aminotransferase (AAT), and adjacent argN, encoding an S-adenosyl methionine (SAM)-dependent methyltransferase, are coupled to catalyze arginine and yield β-methylarginine in Escherichia coli. Purified ArgM can transfer the α-amino group of l-arginine to α-ketoglutaric acid to give glutamate and thereby converts l-arginine to 5-guanidino-2-oxopentanoic acid, which is methylated at the C-3 position by ArgN to form 5-guanidino-3-methyl-2-oxopentanoic acid. Iteratively, ArgM specifically catalyzes transamination from the donor l-aspartate to the resulting 5-guanidino-3-methyl-2-oxopentanoic acid, generating β-methylarginine. The complete and concise biosynthetic pathway for the rare and bioactive amino acid revealed by this study may pave the way for the production of β-methylarginine either by enzymatic conversion or by engineered living cells.
2. Complete genome sequence of Streptomyces griseochromogenes ATCC 14511T, a producer of nucleoside compounds and diverse secondary metabolites
Lijuan Wu, Guoqing Chen, Guozhong Feng J Biotechnol. 2017 May 10;249:16-19. doi: 10.1016/j.jbiotec.2017.03.017. Epub 2017 Mar 22.
ATCC 14511T (=DSM 40499, =NBRC 13413) is a type strain of Streptomyces griseochromogenes. It is known as a producer of nucleoside antibiotic, blasticidin S. In this report we present the complete genome sequence of S. griseochromogenes ATCC 14511T, which consists of 10,764,674bp with a linear chromosome, 9822 protein-coding genes, 6 rRNA operons, 74 tRNA and 3 sRNA. The genomic analysis revealed that 52 putative gene clusters are involved in the biosynthesis of secondary metabolites, including four gene clusters of nucleoside antibiotics. These gene clusters provide a beneficial source for production of bioactive natural compounds.
3. Nucleoside antibiotics: biosynthesis, regulation, and biotechnology
Guoqing Niu, Huarong Tan Trends Microbiol. 2015 Feb;23(2):110-9. doi: 10.1016/j.tim.2014.10.007. Epub 2014 Nov 13.
The alarming rise in antibiotic-resistant pathogens has coincided with a decline in the supply of new antibiotics. It is therefore of great importance to find and create new antibiotics. Nucleoside antibiotics are a large family of natural products with diverse biological functions. Their biosynthesis is a complex process through multistep enzymatic reactions and is subject to hierarchical regulation. Genetic and biochemical studies of the biosynthetic machinery have provided the basis for pathway engineering and combinatorial biosynthesis to create new or hybrid nucleoside antibiotics. Dissection of regulatory mechanisms is leading to strategies to increase the titer of bioactive nucleoside antibiotics.
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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 ╳
