Lactimidomycin | CAS#134869-15-1 | glutarimide antibiotic

MedKoo Cat#: 598222 | Name: Lactimidomycin

Description:

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

Lactimidomycin is a glutarimide antibiotic isolated from Streptomyces amphibiosporus.

Chemical Structure

Lactimidomycin

CAS#134869-15-1

Theoretical Analysis

MedKoo Cat#: 598222

Name: Lactimidomycin

CAS#: 134869-15-1

Chemical Formula: C26H35NO6

Exact Mass: 457.2464

Molecular Weight: 457.56

Elemental Analysis: C, 68.25; H, 7.71; N, 3.06; O, 20.98

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Lactimidomycin;

IUPAC/Chemical Name

4-((E)-2-hydroxy-5-methyl-7-((4E,6Z,10Z)-3-methyl-12-oxooxacyclododeca-4,6,10-trien-2-yl)-4-oxooct-6-en-1-yl)piperidine-2,6-dione

InChi Key

OYOKHBHOTQDIPM-DXTDVJPQSA-N

InChi Code

InChI=1S/C26H35NO6/c1-17-10-8-6-4-5-7-9-11-25(32)33-26(17)19(3)12-18(2)22(29)16-21(28)13-20-14-23(30)27-24(31)15-20/h4,6,8-12,17-18,20-21,26,28H,5,7,13-16H2,1-3H3,(H,27,30,31)/b6-4-,10-8+,11-9-,19-12+

SMILES Code

O=C(CC(CC(O)CC(C(C)/C=C(C(C(C)/C=C/C=C\CC/C=C\1)OC1=O)\C)=O)C2)NC2=O

Appearance

Solid powder

Purity

>98% (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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 457.56 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.

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

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Synthesis of eukaryotic translation elongation inhibitor lactimidomycin via Zn(II)-mediated Horner-Wadsworth-Emmons macrocyclization. Org Lett. 2013 Jun 21;15(12):2998-3001. doi: 10.1021/ol401186f. Epub 2013 Jun 3. PubMed PMID: 23731327. 6: Seo JW, Ma M, Kwong T, Ju J, Lim SK, Jiang H, Lohman JR, Yang C, Cleveland J, Zazopoulos E, Farnet CM, Shen B. Comparative characterization of the lactimidomycin and iso-migrastatin biosynthetic machineries revealing unusual features for acyltransferase-less type I polyketide synthases and providing an opportunity to engineer new analogues. Biochemistry. 2014 Dec 16;53(49):7854-65. doi: 10.1021/bi501396v. Epub 2014 Dec 1. PubMed PMID: 25405956; PubMed Central PMCID: PMC4270375. 7: Micoine K, Persich P, Llaveria J, Lam MH, Maderna A, Loganzo F, Fürstner A. Total syntheses and biological reassessment of lactimidomycin, isomigrastatin and congener glutarimide antibiotics. Chemistry. 2013 Jun 3;19(23):7370-83. doi: 10.1002/chem.201300393. 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