| Revision as of 23:10, 27 November 2011 editThe chemistds (talk | contribs)Extended confirmed users5,761 edits added CSID, (Std)InChI & (Std)InChIKey |
Latest revision as of 04:47, 22 November 2024 edit Graeme Bartlett (talk | contribs)Administrators250,103 editsm →top: link |
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| verifiedrevid = 397291355 |
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| verifiedrevid = 462805586 |
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|ImageFile=Blasticidin S.png |
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| ImageFile=Blasticidin A.png |
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|ImageSize=200px |
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| ImageSize=270px |
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| IUPACName= 1-methyl-3-triacont-2-enylidene]pyrrolidine-2,4-dione |
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|IUPACName=4-amino-1-(methyl)amino]pentanoyl}amino)-2,3,4-trideoxy-β-<small>D</small>-''erythro''-hex-2-enopyranuronosyl]pyrimidin-2(1''H'')-one |
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|OtherNames= |
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| OtherNames= |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo_Ref = {{cascite|changed|??}} |
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| CASNo=2079-00-7 |
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| CASNo=100513-53-9 |
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| PubChem=258 |
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| PubChem=76169554 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 476894 |
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| ChEBI = |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| KEGG = C02010 |
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| ChEMBL = |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| ChemSpiderID = 148673 |
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| KEGG = |
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| SMILES = O=C1\N=C(\N)/C=C\N1\2O(C(=O)O)(/C=C/2)NC(=O)C(N)CCN(C(=)N)C |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| 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 |
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| ChemSpiderID = 68004077 |
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| InChIKey = CXNPLSGKWMLZPZ-ZNIXKSQXBS |
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| SMILES = CCCCCCCCCCC(CC1(C(C(C(C(O1)CC(C(C(C(C(CC(CC(CC(CC(C(C)C(C(C)C(CC(C(C)C(C(CC(C)CC(C)/C=C(\C)/C(=C/2\C(=O)CN(C2=O)C)/O)O)O)O)O)O)O)O)O)O)O)O)O)O)O)O)O)O)O)O |
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| StdInChI = 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 |
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| StdInChI=1S/C58H107NO23/c1-9-10-11-12-13-14-15-16-17-35(60)27-58(81)56(79)55(78)53(76)46(82-58)26-44(69)52(75)54(77)51(74)43(68)24-38(63)22-36(61)21-37(62)23-39(64)32(5)49(72)33(6)40(65)25-41(66)34(7)50(73)42(67)20-30(3)18-29(2)19-31(4)48(71)47-45(70)28-59(8)57(47)80/h19,29-30,32-44,46,49-56,60-69,71-79,81H,9-18,20-28H2,1-8H3 |
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| StdInChIKey = CXNPLSGKWMLZPZ-ZNIXKSQXSA-N |
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| StdInChIKey = VVBSMETZVCGSHB-UHFFFAOYSA-N |
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}} |
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}} |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=17|H=26|N=8|O=5 |
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| C=58 | H=107 | N=1 | O=23 |
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| MolarMass=422.44 g/mol |
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| MolarMass=1186.463 g/mol |
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| Appearance= |
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}} |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards= |
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| FlashPt= |
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| AutoignitionPt = |
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}} |
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'''Blasticidin A''' is an ] produced by ''Streptomyces sp.'' that has ] and ] activity. The antibiotic function and structure of blasticidin A has been observed since 1955 by Fukunaga et al. in which the blasticidin A resembles ].<ref>Biologically Active Natural Products: Argochemicals. Cutler G. G., Cutler S. J.; p 193-198. (1999)</ref> |
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'''Blasticidin S''' is an ] that is produced by ''Streptomyces griseochromogenes''. In biological research, specifically ], it is used to select transformed cells which have been engineered to carry a resistance gene for blasticidin. In short, ] 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. |
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== Resistance genes == |
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Three resistance genes have been cloned: |
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* bls (an ]) from ''Streptoverticillum sp.'' which itself produces blasticidin in a natural example of biological warfare |
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* bsr (a ]) from ''Bacillus cereus'' (other bsr genes are known as well, see listings in ]) |
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* BSD (another ]) from ''Aspergillus terreus'' |
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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. |
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== Mechanism of action == |
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Blasticidin prevents the growth of both ] and ] cells. It works by inhibiting peptide bond formation by the ]. This means that cells can no longer produce new proteins through ] of ]. |
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== References == |
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== References == |
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{{reflist}} |
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{{antibiotic-stub}} |
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