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Safety Information

K1507

Sigma-Aldrich

Kirromycin from Streptomyces collinus

Synonym(s):

Antibiotic Myc-8003, Mocimycin

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About This Item

Empirical Formula (Hill Notation):
C43H60N2O12
CAS Number:
50935-71-2
Molecular Weight:
796.94
EC Number:
256-859-9
MDL number:
MFCD00467139
UNSPSC Code:
51102829
PubChem Substance ID:
24896207
NACRES:
NA.85

biological source

Streptomyces collinus

Quality Level

200

form

powder

color

yellow

solubility

methanol: 1.90-2.10 mg/mL, clear, yellow

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

protein synthesis | interferes

storage temp.

−20°C

SMILES string

CCC(C(=O)NC\C=C\C=C(/C)C(OC)C(C)C1OC(\C=C\C=C\C=C(/C)C(=O)C2=C(O)C=CNC2=O)C(O)C1O)C3(O)OC(\C=C\C=C\C)C(C)(C)C(O)C3O

InChI

1S/C43H60N2O12/c1-9-11-13-21-31-42(6,7)38(50)39(51)43(54,57-31)28(10-2)40(52)44-23-17-16-19-26(4)36(55-8)27(5)37-35(49)34(48)30(56-37)20-15-12-14-18-25(3)33(47)32-29(46)22-24-45-41(32)53/h9,11-22,24,27-28,30-31,34-39,48-51,54H,10,23H2,1-8H3,(H,44,52)(H2,45,46,53)/b11-9+,14-12+,17-16+,20-15+,21-13+,25-18+,26-19+

InChI key

HMSYAPGFKGSXAJ-DSMBXYKSSA-N

General description

Chemical structure: polyene

Application

Kirromycin is a polyketide antibiotic which is produced by the actinomycetes Streptomyces collinus. Kirromycin has been used to stimulate GTPase action of EF-Tu in the absence of programmed ribosomes in Thermus thermophilus. Kirromycin is used to study bacterial protein synthesis at the level of elongation factor EF-Tu-GDP release.

Biochem/physiol Actions

Binding of kirromycin to EF-Tu prevents EF-TuGDP from being ejected from the ribosome, which immobilizes the ribsome, as well as all of the following ribosomes on the mRNA.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

监管及禁止进口产品

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Certificates of Analysis (COA)

Lot/Batch Number
119M4018V
14151001
046M4040V
046M4040
040M4018

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D Hughes
Journal of molecular biology, 297(2), 355-364 (2000-03-15)
The tufA and tufB genes in Salmonella typhimurium co-evolve by recombination and exchange of genetic material. A model is presented which predicts that co-evolution is achieved by gene conversions and chromosomal inversions. Analysis of recombinants reveals that conversion and inversion
A M Zuurmond et al.
Journal of molecular biology, 294(3), 627-637 (1999-12-28)
For clarification of the action of a new antibiotic, the analysis of resistant mutants is often indispensable. For enacyloxin IIa we discovered four resistant elongation factor Tu (EF-Tu) species in Escherichia coli with the mutations Q124K, G316D, Q329H, and A375T
Structural biology. A glimpse into tmRNA-mediated ribosome rescue.
Sean D Moore et al.
Science (New York, N.Y.), 300(5616), 72-73 (2003-04-05)
Lian N Olsthoorn-Tieleman et al.
Journal of bacteriology, 189(9), 3581-3590 (2007-03-06)
The antibiotic kirromycin inhibits prokaryotic protein synthesis by immobilizing elongation factor Tu (EF-Tu) on the elongating ribosome. Streptomyces ramocissimus, the producer of kirromycin, contains three tuf genes. While tuf1 and tuf2 encode kirromycin-sensitive EF-Tu species, the function of tuf3 is
Jan-Christian Schuette et al.
The EMBO journal, 28(6), 755-765 (2009-02-21)
We have used single-particle reconstruction in cryo-electron microscopy to determine a structure of the Thermus thermophilus ribosome in which the ternary complex of elongation factor Tu (EF-Tu), tRNA and guanine nucleotide has been trapped on the ribosome using the antibiotic
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