Blasticidin S

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).
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Blasticidin S is an antibiotic that is used in biology research for selecting cells in cell culture. Cells of interest can express the blasticidin resistance genes BSD or bsr, and can then survive treatment with the antibiotic. Blasticidin S is a nucleoside analogue antibiotic, resembling the nucleoside cytidine. Blasticidin works against human cells, fungi, and bacteria, all by disrupting protein translation. It was originally described by Japanese researchers in the 1950s seeking antibiotics for rice blast fungus.