Saphenamycin

For research use only. Not for therapeutic Use.

  • CAT Number: I035988
  • CAS Number: 634600-55-8
  • Molecular Formula: C23H18N2O5
  • Molecular Weight: 402.40
  • Purity: 98%
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Saphenamycin(Cat No.:I035988)is a naturally occurring antibiotic compound isolated from Streptomyces species. It exhibits antimicrobial properties, particularly effective against Gram-positive bacteria. Saphenamycin’s mechanism of action involves inhibiting bacterial cell wall synthesis, making it a potential candidate for treating infections caused by resistant bacteria. It has shown promising activity in preclinical studies, including antimicrobial and antitumor effects. Due to its potent biological activity, Saphenamycin is under investigation for its broader therapeutic applications. Ongoing research aims to understand its full spectrum of activity, optimize its pharmacological properties, and assess its safety for clinical use.


Catalog Number I035988
CAS Number 634600-55-8
Synonyms

Saphenamycin; Racemic ssaphenamycin;

Molecular Formula C23H18N2O5
Purity 98%
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)oxyethyl]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 CC1=C(C(=CC=C1)O)C(=O)OC(C)C2=C3C(=CC=C2)N=C4C(=N3)C=CC=C4C(=O)O
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.

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