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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[1]. 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[2].

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

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

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Mariorosario Masullo et al.
Biochemistry, 41(49), 14482-14488 (2002-12-05)
Valine 114 in the D(109)AAILVVA sequence of elongation factor 1alpha from the archaeon Sulfolobus solfataricus (SsEF-1alpha) was substituted with an acidic (V114E), basic (V114K), or cavity-forming (V114A) residue, and the effects on the biochemical properties of the factor were investigated.
H Rutthard et al.
The Journal of biological chemistry, 276(22), 18728-18733 (2001-03-29)
The influence of divalent metal ions on the intrinsic and kirromycin-stimulated GTPase activity in the absence of programmed ribosomes and on nucleotide binding affinity of elongation factor Tu (EF-Tu) from Thermus thermophilus prepared as the nucleotide- and Mg(2+)-free protein has
Subir Biswas et al.
International journal for parasitology, 41(3-4), 417-427 (2010-12-18)
Protein translation in the plastid (apicoplast) of Plasmodium spp. is of immense interest as a target for potential anti-malarial drugs. However, the molecular data on apicoplast translation needed for optimisation and development of novel inhibitors is lacking. We report characterisation
C C Hall et al.
Antimicrobial agents and chemotherapy, 33(3), 322-325 (1989-03-01)
Six kirromycin analogs (elfamycins) were compared on the basis of their inhibition of Escherichia coli poly(U)-directed poly(Phe) synthesis and stimulation of elongation factor Tu (EF-Tu)-associated GTPase activity. The elfamycins tested were kirromycin, aurodox, efrotomycin, phenelfamycin A, unphenelfamycin, and L-681,217. The
Lian N Olsthoorn-Tieleman et al.
Journal of bacteriology, 184(15), 4211-4218 (2002-07-11)
Streptomyces ramocissimus, the producer of elongation factor Tu (EF-Tu)-targeted antibiotic kirromycin, contains three divergent tuf-like genes, with tuf1 encoding regular kirromycin-sensitive EF-Tu1; the functions of tuf2 and tuf3 are unknown. Analysis of the tuf gene organization in nine producers of
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