Synonym
Antibiotic JI 20A; BRN 1668513; BRN1668513; BRN-1668513; JI-20 A;
IUPAC/Chemical Name
(2S,3S,4R,5S,6S)-5-amino-2-(aminomethyl)-6-(((1S,2S,3R,4S,6S)-4,6-diamino-3-(((2S,3S,4R,5S)-3,5-dihydroxy-5-methyl-4-(methylamino)tetrahydro-2H-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)tetrahydro-2H-pyran-3,4-diol
InChi Key
YQGZDAPJXRYYLX-NNLKOIBQSA-N
InChi Code
InChI=1S/C19H39N5O9/c1-19(29)5-30-18(13(28)16(19)24-2)33-15-7(22)3-6(21)14(12(15)27)32-17-9(23)11(26)10(25)8(4-20)31-17/h6-18,24-29H,3-5,20-23H2,1-2H3/t6-,7-,8-,9-,10+,11+,12-,13-,14-,15+,16+,17-,18-,19+/m0/s1
SMILES Code
N[C@@H]1[C@H]([C@H]([C@H]([C@H](C1)N)O[C@@H]2O[C@H]([C@H]([C@H](O)[C@@H]2N)O)CN)O)O[C@@H]3OC[C@@](C)(O)[C@H](NC)[C@@H]3O
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
481.54
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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2: Guo J, Huang F, Huang C, Duan X, Jian X, Leeper F, Deng Z, Leadlay PF, Sun Y. Specificity and promiscuity at the branch point in gentamicin biosynthesis. Chem Biol. 2014 May 22;21(5):608-18. doi: 10.1016/j.chembiol.2014.03.005. Epub 2014 Apr 17. PubMed PMID: 24746560; PubMed Central PMCID: PMC4039129.
3: Shao L, Chen J, Wang C, Li JA, Tang Y, Chen D, Liu W. Characterization of a key aminoglycoside phosphotransferase in gentamicin biosynthesis. Bioorg Med Chem Lett. 2013 Mar 1;23(5):1438-41. doi: 10.1016/j.bmcl.2012.12.064. Epub 2013 Jan 3. PubMed PMID: 23339967.
4: Park JW, Hong JS, Parajuli N, Koh HS, Park SR, Lee MO, Lim SK, Yoon YJ. Analytical profiling of biosynthetic intermediates involved in the gentamicin pathway of Micromonospora echinospora by high-performance liquid chromatography using electrospray ionization mass spectrometric detection. Anal Chem. 2007 Jul 1;79(13):4860-9. Epub 2007 May 24. PubMed PMID: 17521166.
5: Lee BK, Nagabhushan TL, Condon RG, Shimonaski G, Kalyanpur MG, Patel M, Waitz JA. Biosynthetic pathway leading to gentamicin C2b. Antimicrob Agents Chemother. 1979 Nov;16(5):589-91. PubMed PMID: 525999; PubMed Central PMCID: PMC352910.
6: Kugelman M, Mallams AK, Vernay HF. Semisynthetic aminoglycoside antibacterials. Part IV. Synthesis of antibiotic JI-20A, gentamicin B, and related compounds. J Chem Soc Perkin 1. 1976;(10):1126-34. PubMed PMID: 945289.
