Blasticidin S

Blasticidin S
Names

IUPAC name 4-amino-1-[4-({(3S)-3-amino-5-[[amino(imino)methyl](methyl)amino]pentanoyl}amino)-2,3,4-trideoxy-β-D-erythro-hex-2-enopyranuronosyl]pyrimidin-2(1H)-one
Identifiers
CAS Number	2079-00-7^Y
ChEBI	CHEBI:15353^N
ChEMBL	ChEMBL476894^Y
ChemSpider	148673^Y
Jmol 3D model	Interactive image
KEGG	C02010^Y
PubChem	258
InChI InChI=1S/C17H26N8O5/c1-24(16(20)21)6-4-9(18)8-12(26)22-10-2-3-13(30-14(10)15(27)28)25-7-5-11(19)23-17(25)29/h2-3,5,7,9-10,13-14H,4,6,8,18H2,1H3,(H3,20,21)(H,22,26)(H,27,28)(H2,19,23,29)/t9-,10-,13+,14-/m0/s1^Y Key: CXNPLSGKWMLZPZ-ZNIXKSQXSA-N^Y InChI=1/C17H26N8O5/c1-24(16(20)21)6-4-9(18)8-12(26)22-10-2-3-13(30-14(10)15(27)28)25-7-5-11(19)23-17(25)29/h2-3,5,7,9-10,13-14H,4,6,8,18H2,1H3,(H3,20,21)(H,22,26)(H,27,28)(H2,19,23,29)/t9-,10-,13+,14-/m0/s1 Key: CXNPLSGKWMLZPZ-ZNIXKSQXBS
SMILES O=C1\N=C(\N)/C=C\N1[C@@H]\2O[C@H](C(=O)O)[C@H](/C=C/2)NC(=O)C[C@@H](N)CCN(C(=[N@H])N)C
Properties
Chemical formula	C₁₇H₂₆N₈O₅
Molar mass	422.44 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

Blasticidin S is an antibiotic that is produced by Streptomyces griseochromogenes. In biological research, specifically genetic engineering, it is used to select transformed cells which have been engineered to carry a resistance gene for blasticidin. In short, DNA of interest is fused to DNA encoding a resistance gene, and then is transformed into cells. After allowing time for recovery and for cells to begin transcribing and translating their new DNA, blasticidin is added. Now only the cells that have the new DNA can grow.

History

In the 1950s, a drug screening program was designed in Japan to discover a new antibiotic that prevents Blast Disease by the fungus Magnaporthe grisea.^[1]

Resistance genes

Three resistance genes have been cloned:

bls (an acetyltransferase) from Streptoverticillum sp. which itself produces blasticidin in a natural example of biological warfare
bsr (a blasticidin-S deaminase) from Bacillus cereus (other bsr genes are known as well, see listings in Genbank)
BSD (another deaminase) from Aspergillus terreus

bsr and BSD are the most commonly used resistance genes. The proteins produced from these genes enable the cells carrying them to produce protein in the presence of blasticidin.

Mechanism of action

Blasticidin prevents the growth of both eukaryotic and prokaryotic cells. It works by inhibiting termination step of translation and peptide bond formation (to lesser extent) by the ribosome. This means that cells can no longer produce new proteins through translation of mRNA.

References

↑ Natural Products Isolation: Separation Methods for Antimicrobials, Antivirals, and Enzyme Inhibitors. Wagman G. H., Elsevier R. C.; p. 191 (1988).

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