Demethylblasticidin S
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| Category | Antibiotics |
| Catalog number | BBF-02022 |
| CAS | 63257-29-4 |
| Molecular Weight | 408.41 |
| Molecular Formula | C16H24N8O5 |
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Description
Demethylblastcidin S is a nucleoside antibiotic produced by Streptomyces griseochromogenes IFO 13413. It has anti-phytopathogenic fungus activity.
Specification
| IUPAC Name | (2S,3S,6R)-3-[[(3S)-3-amino-5-(diaminomethylideneamino)pentanoyl]amino]-6-(4-amino-2-oxopyrimidin-1-yl)-3,6-dihydro-2H-pyran-2-carboxylic acid |
| Canonical SMILES | C1=CC(OC(C1NC(=O)CC(CCN=C(N)N)N)C(=O)O)N2C=CC(=NC2=O)N |
| InChI | InChI=1S/C16H24N8O5/c17-8(3-5-21-15(19)20)7-11(25)22-9-1-2-12(29-13(9)14(26)27)24-6-4-10(18)23-16(24)28/h1-2,4,6,8-9,12-13H,3,5,7,17H2,(H,22,25)(H,26,27)(H2,18,23,28)(H4,19,20,21)/t8-,9-,12+,13-/m0/s1 |
| InChI Key | OJVBAQZCFZMOBW-NGERZBJRSA-N |
Properties
| Appearance | Colorless Flake Crystal |
| Antibiotic Activity Spectrum | fungi |
| Melting Point | 244-248°C (dec.) |
| Density | 1.7±0.1 g/cm3 |
Reference Reading
1. Guanidine N-methylation by BlsL Is Dependent on Acylation of Beta-amine Arginine in the Biosynthesis of Blasticidin S
Xiankun Wang, Aiqin Du, Guiyang Yu, Zixin Deng, Xinyi He Front Microbiol. 2017 Aug 22;8:1565. doi: 10.3389/fmicb.2017.01565. eCollection 2017.
The peptidyl nucleoside blasticidin S (BS) produced by Streptomyces griseochromogenes was the first non-mercurial fungicide used to prevent rice blast and increasingly used as a selection reagent in transgenic study. Acylation by addition of a leucine residue at the beta amine group of arginine side chain of demethylblasticidin S (DBS) has been proposed as a novel self-resistance to the cytotoxic biosynthetic intermediate. But the resultant product leucyldemethylblasticidin S (LDBS) has not been isolated as a metabolite, and LDBS synthetase activity remained to be demonstrated in S. griseochromogenes. In this study, we isolated LDBS in a BS heterologous producer S. lividans WJ2 upon the deletion of blsL, which encodes a S-Adenosyl methionine-dependent methyltransferase. Purified BlsL efficiently methylated LDBS at the delta N of beta-arginine to generate the ultimate intermediate LBS, but nearly didn't methylate DBS to final product BS. Above experiments demonstrated that LDBS is indeed an intermediate in BS biosynthetic pathway, and acylation of beta-amino group of arginine side chain is prerequisite for efficient guanidine N-methylation in addition to being a self-resistance mechanism.
2. Cloning and heterologous expression of blasticidin S biosynthetic genes from Streptomyces griseochromogenes
M C Cone, A K Petrich, S J Gould, T M Zabriskie J Antibiot (Tokyo). 1998 Jun;51(6):570-8. doi: 10.7164/antibiotics.51.570.
Two small chromosomal DNA fragments (2.6 and 4.8 kb) from the blasticidin S producer Streptomyces griseochromogenes were cloned in the high copy number vector pIJ702 and shown to confer increased resistance to blasticidin S upon S. lividans TK24. These fragments were used to screen a library of S. griseochromogenes DNA prepared in the cosmid shuttle vector pOJ446. Cosmids containing DNA inserts of at least 23 kb were identified which hybridized to one or the other resistance fragment, but not to both. Transformation of S. lividans TK24 with several cosmids hybridizing with the 4.8 kb resistance fragment resulted in clones that produced cytosylglucuronic acid, the first intermediate of the blasticidin S biosynthetic pathway, and other blasticidin-related metabolites. A strain of S. lividans TK24 harboring both the 4.8 kb-hybridizing cosmid and the 2.6 kb resistance fragment cloned in pIJ702 produced 12.5 times as much demethylblasticidin S as the transformant harboring the cosmid alone.
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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 ╳
