MedKoo Cat#: 584988 | Name: Kirromycin
Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Kirromycin is a polyketide antibiotic produced by Streptomyces collinus that functions as a potent inhibitor of bacterial protein synthesis. It exerts its effect by binding to elongation factor Tu (EF-Tu), stabilizing the EF-Tu·GDP·aminoacyl-tRNA complex on the ribosome, thereby preventing the release of EF-Tu and halting translation. This unique mechanism distinguishes kirromycin from ribosome-targeting antibiotics and has made it a valuable tool in studying EF-Tu function and antibiotic resistance mechanisms.

Chemical Structure

Kirromycin
Kirromycin
CAS#50935-71-2 (free acid)

Theoretical Analysis

MedKoo Cat#: 584988

Name: Kirromycin

CAS#: 50935-71-2 (free acid)

Chemical Formula: C43H60N2O12

Exact Mass: 796.4146

Molecular Weight: 796.96

Elemental Analysis: C, 64.81; H, 7.59; N, 3.52; O, 24.09

Price and Availability

Size Price Availability Quantity
1mg USD 950.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Synonym
Kirromycin; Mocimycin
IUPAC/Chemical Name
(alphaS,2R,3R,4R,6S)-N-[(2E,4E,6S,7R)-7-[(2S,3S,4R,5R)-5-[(1E,3E,5E)-7-(1,2-dihydro-4-hydroxy-2-oxo-3-pyridinyl)-6-methyl-7-oxo-1,3,5-heptatrien-1-yl]tetrahydro-3,4-dihydroxy-2-furanyl]-6-methoxy-5-methyl-2,4-octadien-1-yl]-alpha-ethyltetrahydro-2,3,4-trihydroxy-5,5-dimethyl-6-(1E,3Z)-1,3-pentadien-1-yl-2H-pyran-2-acetamide
InChi Key
HMSYAPGFKGSXAJ-PAHGNTJYSA-N
InChi Code
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+/t27-,28-,30-,31+,34+,35+,36-,37+,38+,39-,43-/m1/s1
SMILES Code
O=C(NC/C=C/C=C(C)/[C@@H](OC)[C@H]([C@@H]1O[C@H](/C=C/C=C/C=C(C)/C(C2=C(O)C=CNC2=O)=O)[C@H](O)[C@@H]1O)C)[C@@H](CC)[C@]3(O)[C@H](O)[C@H](O)C(C)(C)[C@H](/C=C/C=C\C)O3
Appearance
Solid powder
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Biological target:
Kirromycin is a bacterial protein synthesis inhibitor that immobilizes elongation factor Tu (EF-Tu) on the elongating ribosome.
In vitro activity:
In conclusion, kirromycin can substitute for GTP, aminoacyl-tRNA, or ribosomes in various reactions involving EF-Tu, apparently by affecting the allosteric controls between the sites on the EF-Tu molecule interacting with these components. Reference: Proc Natl Acad Sci U S A. 1974 Dec;71(12):4910-4. https://pubmed.ncbi.nlm.nih.gov/4373734/
In vivo activity:
TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 796.96 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Wolf H, Chinali G, Parmeggiani A. Kirromycin, an inhibitor of protein biosynthesis that acts on elongation factor Tu. Proc Natl Acad Sci U S A. 1974 Dec;71(12):4910-4. doi: 10.1073/pnas.71.12.4910. PMID: 4373734; PMCID: PMC434009. 2. Wolf H, Zähner H, Nierhaus K. Kirromycin, an inhibitor of the 30 S ribosomal subunits function. FEBS Lett. 1972 Apr 1;21(3):347-350. doi: 10.1016/0014-5793(72)80199-6. PMID: 11946543.
In vitro protocol:
1. Wolf H, Chinali G, Parmeggiani A. Kirromycin, an inhibitor of protein biosynthesis that acts on elongation factor Tu. Proc Natl Acad Sci U S A. 1974 Dec;71(12):4910-4. doi: 10.1073/pnas.71.12.4910. PMID: 4373734; PMCID: PMC434009. 2. Wolf H, Zähner H, Nierhaus K. Kirromycin, an inhibitor of the 30 S ribosomal subunits function. FEBS Lett. 1972 Apr 1;21(3):347-350. doi: 10.1016/0014-5793(72)80199-6. PMID: 11946543.
In vivo protocol:
TBD
1. Wolf, H., Zähner, H., and Nierhaus, K. Kirromycin, an inhibitor of the 30 S ribosomal subunits function FEBS Lett. 21(3), 347-350 (1972). 2. Wolf, H., Chinali, G., and Parmeggiani, A. Kirromycin, an inhibitor of protein biosynthesis that acts on elongation factor Tu Proc. Nat. Acad. Sci. USA 71(12), 4910-4914 (1974).