Synonym
Saphenamycin; Racemic ssaphenamycin;
IUPAC/Chemical Name
6-(1-((2-hydroxy-6-methylbenzoyl)oxy)ethyl)phenazine-1-carboxylic acid
InChi Key
AXHGAUSFRHOIGV-UHFFFAOYSA-N
InChi Code
InChI=1S/C23H18N2O5/c1-12-6-3-11-18(26)19(12)23(29)30-13(2)14-7-4-9-16-20(14)24-17-10-5-8-15(22(27)28)21(17)25-16/h3-11,13,26H,1-2H3,(H,27,28)
SMILES Code
CC(c(ccc1)c2c1nc(c(C(O)=O)ccc3)c3n2)OC(c4c(O)cccc4C)=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
402.40
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: Rui Z, Ye M, Wang S, Fujikawa K, Akerele B, Aung M, Floss HG, Zhang W, Yu TW. Insights into a divergent phenazine biosynthetic pathway governed by a plasmid-born esmeraldin gene cluster. Chem Biol. 2012 Sep 21;19(9):1116-25. doi: 10.1016/j.chembiol.2012.07.025. PubMed PMID: 22999880.
2: Laursen JB, de Visser PC, Nielsen HK, Jensen KJ, Nielsen J. Solid-phase synthesis of new saphenamycin analogues with antimicrobial activity. Bioorg Med Chem Lett. 2002 Jan 21;12(2):171-5. PubMed PMID: 11755347.
3: Laursen JB, Jørgensen CG, Nielsen J. First synthesis of racemic saphenamycin and its enantiomers. investigation of biological activity. Bioorg Med Chem. 2003 Mar 6;11(5):723-31. PubMed PMID: 12538002.
4: Bahnmüller U, Keller-Schierlein W, Brandl M, Zähner H, Diddens H. Metabolites of microorganisms. 248. Synthetic analogs of saphenamycin. J Antibiot (Tokyo). 1988 Nov;41(11):1552-60. PubMed PMID: 3198490.
5: Kitahara M, Nakamura H, Matsuda Y, Hamada M, Naganawa H, Maeda K, Umezawa H, Iitaka Y. Saphenamycin, a novel antibiotic from a strain of Streptomyces. J Antibiot (Tokyo). 1982 Oct;35(10):1412-4. PubMed PMID: 7174526.
6: Geiger A, Keller-Schierlein W, Brandl M, Zähner H. Metabolites of microorganisms. 247. Phenazines from Streptomyces antibioticus, strain Tü 2706. J Antibiot (Tokyo). 1988 Nov;41(11):1542-51. PubMed PMID: 3058669.
7: Laursen JB, Petersen L, Jensen KJ, Nielsen J. Efficient synthesis of glycosylated phenazine natural products and analogs with DISAL (methyl 3,5-dinitrosalicylate) glycosyl donors. Org Biomol Chem. 2003 Sep 21;1(18):3147-53. PubMed PMID: 14527145.
