Kasugamycin | CAS#6980-18-3 | antibiotic

MedKoo Cat#: 561661 | Name: Kasugamycin

Description:

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

Kasugamycin is an antibiotic. It acts by binding within the mRNA channel of the 30S subunit and inhibiting protein synthesis.

Chemical Structure

Kasugamycin

CAS#6980-18-3 (free base)

Theoretical Analysis

MedKoo Cat#: 561661

Name: Kasugamycin

CAS#: 6980-18-3 (free base)

Chemical Formula: C14H25N3O9

Exact Mass: 379.1591

Molecular Weight: 379.36

Elemental Analysis: C, 44.33; H, 6.64; N, 11.08; O, 37.96

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.

Bulk Inquiry

Related CAS #

78822-08-9 (sulfate) 6980-18-3 (free base)

Synonym

Kasugamycin;

IUPAC/Chemical Name

2-Amino-2-[(2R,3S,5S,6R)-5-amino-2-methyl-6-[(2S,3S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxyoxan-3-yl]iminoacetic acid

InChi Key

PVTHJAPFENJVNC-UQTMRZPGSA-N

InChi Code

InChI=1S/C14H25N3O9/c1-3-5(17-12(16)13(23)24)2-4(15)14(25-3)26-11-9(21)7(19)6(18)8(20)10(11)22/h3-11,14,18-22H,2,15H2,1H3,(H2,16,17)(H,23,24)/t3-,4+,5+,6?,7+,8+,9-,10+,11?,14-/m1/s1

SMILES Code

O=C(O)/C(N)=N/[C@@H]1[C@@H](C)O[C@H](OC2[C@@H](O)[C@@H](O)C(O)[C@H](O)[C@H]2O)[C@@H](N)C1

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

>2 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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 379.36 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

1: Zhang H, Wang C, Li H, Nie Y, Fang L, Chen Z. Simultaneous determination of kasugamycin and validamycin-A residues in cereals by consecutive solid-phase extraction combined with liquid chromatography-tandem mass spectrometry. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2017 Dec 6. doi: 10.1080/19440049.2017.1411615. [Epub ahead of print] PubMed PMID: 29210618. 2: Usachev KS, Ayupov RK, Validov SZ, Khusainov IS, Yusupov MM. NMR assignments of the N-terminal domain of Staphylococcus aureus hibernation promoting factor (SaHPF). Biomol NMR Assign. 2017 Oct 4. doi: 10.1007/s12104-017-9783-2. [Epub ahead of print] PubMed PMID: 28980143. 3: Shiver AL, Osadnik H, Kritikos G, Li B, Krogan N, Typas A, Gross CA. Correction: A Chemical-Genomic Screen of Neglected Antibiotics Reveals Illicit Transport of Kasugamycin and Blasticidin S. PLoS Genet. 2017 Jul 21;13(7):e1006902. doi: 10.1371/journal.pgen.1006902. eCollection 2017 Jul. PubMed PMID: 28732023; PubMed Central PMCID: PMC5521741. 4: Fan C, Guo M, Liang Y, Dong H, Ding G, Zhang W, Tang G, Yang J, Kong D, Cao Y. Pectin-conjugated silica microcapsules as dual-responsive carriers for increasing the stability and antimicrobial efficacy of kasugamycin. Carbohydr Polym. 2017 Sep 15;172:322-331. doi: 10.1016/j.carbpol.2017.05.050. Epub 2017 May 21. PubMed PMID: 28606541. 5: Kasuga K, Sasaki A, Matsuo T, Yamamoto C, Minato Y, Kuwahara N, Fujii C, Kobayashi M, Agematu H, Tamura T, Komatsu M, Ishikawa J, Ikeda H, Kojima I. Heterologous production of kasugamycin, an aminoglycoside antibiotic from Streptomyces kasugaensis, in Streptomyces lividans and Rhodococcus erythropolis L-88 by constitutive expression of the biosynthetic gene cluster. Appl Microbiol Biotechnol. 2017 May;101(10):4259-4268. doi: 10.1007/s00253-017-8189-5. Epub 2017 Feb 27. PubMed PMID: 28243709. 6: Castillo-González H, Pérez-Villanueva M, Masís-Mora M, Castro-Gutiérrez V, Rodríguez-Rodríguez CE. Antibiotics do not affect the degradation of fungicides and enhance the mineralization of chlorpyrifos in biomixtures. Ecotoxicol Environ Saf. 2017 May;139:481-487. doi: 10.1016/j.ecoenv.2017.02.008. Epub 2017 Feb 23. PubMed PMID: 28214645. 7: Lange C, Lehr M, Zerulla K, Ludwig P, Schweitzer J, Polen T, Wendisch VF, Soppa J. Effects of Kasugamycin on the Translatome of Escherichia coli. PLoS One. 2017 Jan 12;12(1):e0168143. doi: 10.1371/journal.pone.0168143. eCollection 2017. PubMed PMID: 28081129; PubMed Central PMCID: PMC5230787. 8: Danezis GP, Anagnostopoulos CJ, Liapis K, Koupparis MA. Multi-residue analysis of pesticides, plant hormones, veterinary drugs and mycotoxins using HILIC chromatography - MS/MS in various food matrices. Anal Chim Acta. 2016 Oct 26;942:121-138. doi: 10.1016/j.aca.2016.09.011. Epub 2016 Sep 20. PubMed PMID: 27720116. 9: Shiver AL, Osadnik H, Kritikos G, Li B, Krogan N, Typas A, Gross CA. A Chemical-Genomic Screen of Neglected Antibiotics Reveals Illicit Transport of Kasugamycin and Blasticidin S. PLoS Genet. 2016 Jun 29;12(6):e1006124. doi: 10.1371/journal.pgen.1006124. eCollection 2016 Jun. Erratum in: PLoS Genet. 2017 Jul 21;13(7):e1006902. PubMed PMID: 27355376; PubMed Central PMCID: PMC4927156. 10: Müller C, Sokol L, Vesper O, Sauert M, Moll I. Insights into the Stress Response Triggered by Kasugamycin in Escherichia coli. Antibiotics (Basel). 2016 Jun 1;5(2). pii: E19. doi: 10.3390/antibiotics5020019. PubMed PMID: 27258317; PubMed Central PMCID: PMC4929434. 11: Maio A, Brandi L, Donadio S, Gualerzi CO. The Oligopeptide Permease Opp Mediates Illicit Transport of the Bacterial P-site Decoding Inhibitor GE81112. Antibiotics (Basel). 2016 May 24;5(2). pii: E17. doi: 10.3390/antibiotics5020017. PubMed PMID: 27231947; PubMed Central PMCID: PMC4929432. 12: Tarusawa T, Ito S, Goto S, Ushida C, Muto A, Himeno H. (p)ppGpp-dependent and -independent pathways for salt tolerance in Escherichia coli. J Biochem. 2016 Jul;160(1):19-26. doi: 10.1093/jb/mvw008. Epub 2016 Jan 27. PubMed PMID: 26823481. 13: Zhu C, Kang Q, Bai L, Cheng L, Deng Z. Identification and engineering of regulation-related genes toward improved kasugamycin production. Appl Microbiol Biotechnol. 2016 Feb;100(4):1811-21. doi: 10.1007/s00253-015-7082-3. Epub 2015 Oct 31. PubMed PMID: 26521251. 14: Liu Y, Sun Y, Ding G, Geng Q, Zhu J, Guo M, Duan Y, Wang B, Cao Y. Synthesis, characterization, and application of microbe-triggered controlled-release kasugamycin-pectin conjugate. J Agric Food Chem. 2015 May 6;63(17):4263-8. doi: 10.1021/jf5055062. Epub 2015 Apr 27. PubMed PMID: 25876441. 15: Ghods S, Sims IM, Moradali MF, Rehm BH. Bactericidal Compounds Controlling Growth of the Plant Pathogen Pseudomonas syringae pv. actinidiae, Which Forms Biofilms Composed of a Novel Exopolysaccharide. Appl Environ Microbiol. 2015 Jun 15;81(12):4026-36. doi: 10.1128/AEM.00194-15. Epub 2015 Apr 3. PubMed PMID: 25841017; PubMed Central PMCID: PMC4524148. 16: Zhang M, Guo Y, Powell CA, Doud MS, Yang C, Duan Y. Effective antibiotics against 'Candidatus Liberibacter asiaticus' in HLB-affected citrus plants identified via the graft-based evaluation. PLoS One. 2014 Nov 5;9(11):e111032. doi: 10.1371/journal.pone.0111032. eCollection 2014. PubMed PMID: 25372135; PubMed Central PMCID: PMC4220982. 17: Shetty S, Nadimpalli H, Shah RA, Arora S, Das G, Varshney U. An extended Shine-Dalgarno sequence in mRNA functionally bypasses a vital defect in initiator tRNA. Proc Natl Acad Sci U S A. 2014 Oct 7;111(40):E4224-33. doi: 10.1073/pnas.1411637111. Epub 2014 Sep 22. PubMed PMID: 25246575; PubMed Central PMCID: PMC4210040. 18: Yoshii A, Omatsu T, Katayama Y, Koyama S, Mizutani T, Moriyama H, Fukuhara T. Two types of genetic carrier, the IncP genomic island and the novel IncP-1β plasmid, for the aac(2')-IIa gene that confers kasugamycin resistance in Acidovorax avenae ssp. avenae. Mol Plant Pathol. 2015 Apr;16(3):288-300. doi: 10.1111/mpp.12182. Epub 2014 Sep 24. PubMed PMID: 25131295. 19: Chiok KL, Addwebi T, Guard J, Shah DH. Dimethyl adenosine transferase (KsgA) deficiency in Salmonella enterica Serovar Enteritidis confers susceptibility to high osmolarity and virulence attenuation in chickens. Appl Environ Microbiol. 2013 Dec;79(24):7857-66. doi: 10.1128/AEM.03040-13. Epub 2013 Oct 11. PubMed PMID: 24123731; PubMed Central PMCID: PMC3837837. 20: Hase Y, Tarusawa T, Muto A, Himeno H. Impairment of ribosome maturation or function confers salt resistance on Escherichia coli cells. PLoS One. 2013 May 31;8(5):e65747. doi: 10.1371/journal.pone.0065747. Print 2013. PubMed PMID: 23741511; PubMed Central PMCID: PMC3669203.