Synonym
Ketomycin; Antibiotic R-3; Antibiotic T 86A; Cyclohexenyl-1-glyoxalic acid;
IUPAC/Chemical Name
3-Cyclohexene-1-acetic acid, alpha-oxo-, (R)- (9CI)
InChi Key
XJVDGWZMESEVTD-LURJTMIESA-N
InChi Code
InChI=1S/C8H10O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-2,6H,3-5H2,(H,10,11)/t6-/m0/s1
SMILES Code
O=C(O)C([C@H]1CC=CCC1)=O
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
154.16
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: Takeda Y, Mak V, Chang CC, Chang CJ, Floss HG. Biosynthesis of ketomycin. J Antibiot (Tokyo). 1984 Aug;37(8):868-75. PubMed PMID: 6384167.
2: Jackson JH, Umbarger HE. Defective transamination, a mechanism for resistance to ketomycin in Escherichia coli. Antimicrob Agents Chemother. 1973 Apr;3(4):510-6. PubMed PMID: 4597727; PubMed Central PMCID: PMC444444.
3: Keller-Schierlein W, Poralla K, Zähner H. [Metabolic products of microorganisms. 78. Isolation, identification and mechanism of action of ketomycin ((R)-3-cyclohexeneglyoxylic acid) and of the conversion product 3-cyclohexeneglycine]. Arch Mikrobiol. 1969;67(4):339-56. German. PubMed PMID: 4985531.
4: Krüpe H, Poralla K. [Properties of mutants of Bacillus subtilis which are resistant to the isoleucine antagonist ketomycin]. Arch Mikrobiol. 1972;85(3):253-8. German. PubMed PMID: 4629239.
5: Momose I, Chen W, Kinoshita N, Iinuma H, Hamada M, Takeuchi T. Polyketomycin, a new antibiotic from Streptomyces sp. MK277-AF1. I. Taxonomy, production, isolation, physico-chemical properties and biological activities. J Antibiot (Tokyo). 1998 Jan;51(1):21-5. PubMed PMID: 9531983.
6: Jackson J, Williams LS, Umbarger HE. Regulation of synthesis of the branched-chain amino acids and cognate aminoacyl-transfer ribonucleic acid synthetases of Escherichia coli: a common regulatory element. J Bacteriol. 1974 Dec;120(3):1380-6. PubMed PMID: 4612020; PubMed Central PMCID: PMC245925.
