Saphenamycin

• CAT Number: I035988
• CAS Number: 634600-55-8
• Molecular Formula: C23H18N2O5
• Molecular Weight: 402.4
• Purity: 98%
• Synonyms: Saphenamycin; Racemic ssaphenamycin
• Target: HIV
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: 6-(1-((2-hydroxy-6-methylbenzoyl)oxy)ethyl)phenazine-1-carboxylic acid
• InChI: 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)
• InChIKey: AXHGAUSFRHOIGV-UHFFFAOYSA-N
• SMILES: CC(c(ccc1)c2c1nc(c(C(O)=O)ccc3)c3n2)OC(c4c(O)cccc4C)=O

Saphenamycin is a novel antibiotic from a strain of Streptomyces.

Reference

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.