Blasticidin S

Source: Wikipedia, the free encyclopedia.
Blasticidin S
Names
Preferred IUPAC name
(2S,3S,6R)-3-{(3S)-3-Amino-5-[carbamimidoyl(methyl)amino]pentanamido}-6-(4-amino-2-oxopyrimidin-1(2H)-yl)-3,6-dihydro-2H-pyran-2-carboxylic acid
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.109.057 Edit this at Wikidata
KEGG
UNII
  • 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 checkY
    Key: CXNPLSGKWMLZPZ-ZNIXKSQXSA-N checkY
  • 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
  • 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
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 checkY☒N ?)

Blasticidin S is an

rice blast fungus
.

Chemistry

Color overlay showing constituent parts of Blasticidin S

A nucleoside analog, blasticidin S resembles the nucleoside cytidine. The chemical structure consists of a cytosine molecule, linked to a glucuronic acid-derived ring, linked in turn to the peptide N-methyl β-arginine.[1]

Uses

Blasticidin S is widely used in

culture media.[2] Blasticidin S is typically used at 2–300 micrograms per milliliter of media, depending on the type of cell being grown.[2]

Mechanism of action

Blasticidin prevents the growth of both

mRNA. It is competitive with puromycin suggesting a highly similar binding site.[3]

Biosynthesis

The first step in blasticidin S biosynthesis is the combination of UDP-glucuronic acid with cytosine to form cytosylglucuronic acid (CGA). Given the product name, the enzyme that performs this combination is called CGA synthase.[1]

Cosmid cloning experiments from the Blasticidin S producer

Streptomyces lividans
, indicated that a 20 Kbp gene cluster with 19 genes, plus possibly a peptidase outside the gene cluster that acts on the final leucylblasticidin S (LBS) intermediate, was sufficient for reconstitution of Blasticidin S biosynthesis.[3]

Resistance genes

deaminases: BSD, originally isolated from Aspergillus terreus or bsr, isolated from Bacillus cereus. Both deaminases work by modifying blasticidin S directly, replacing the amine on the cytosine ring with a hydroxyl group, resulting in the inactive deaminohydroxy-blasticin S.[2][4]

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

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.[5]

References

  1. ^
    PMID 25468791
    .
  2. ^ a b c "Blasticidin S HCl Protocols". ThermoFisher Scientific. Retrieved 22 April 2021.
  3. ^
    S2CID 20991778
    .
  4. ISBN 9780444507396
    .
  5. ^ Natural Products Isolation: Separation Methods for Antimicrobials, Antivirals, and Enzyme Inhibitors. Wagman G. H., Elsevier R. C.; p. 191 (1988).

External links

Retrieved from "https://en.wikipedia.org/w/index.php?title=Blasticidin_S&oldid=1189056712"