Aurantimycin A

Aurantimycin A

Names
IUPAC name (2R)-N-[(6S,9R,16S,17S,20R,23S)-7,21-dihydroxy-6-(methoxymethyl)-20-methyl-2,5,8,15,19,22-hexaoxo-17-propan-2-yl-18-oxa-1,4,7,13,14,21,27-heptazatricyclo[21.4.0.09,14]heptacosan-16-yl]-2-hydroxy-2-[(2S,5S,6S)-2-hydroxy-6-methyl-5-(2-methylpropyl)oxan-2-yl]propanamide [1]
Other names Aurantimycin
Identifiers
CAS Number	162478-50-4  Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1241097
ChemSpider	8277625
PubChem CID	10102093
InChI InChI=1S/C38H64N8O14/c1-20(2)17-24-13-14-38(55,60-23(24)6)37(7,54)36(53)42-29-30(21(3)4)59-35(52)22(5)45(56)32(49)25-11-9-15-40-43(25)28(47)18-39-31(48)27(19-58-8)46(57)33(50)26-12-10-16-41-44(26)34(29)51/h20-27,29-30,40-41,54-57H,9-19H2,1-8H3,(H,39,48)(H,42,53)/t22-,23+,24+,25+,26-,27+,29+,30+,37+,38+/m1/s1 Key: JSVPJXYQXDNLRD-NSCUIBACSA-N
SMILES C[C@H]1[C@@H](CC[C@](O1)([C@](C)(C(=O)N[C@H]2[C@@H](OC(=O)[C@H](N(C(=O)[C@@H]3CCCNN3C(=O)CNC(=O)[C@@H](N(C(=O)[C@H]4CCCNN4C2=O)O)COC)O)C)C(C)C)O)O)CC(C)C
Properties
Chemical formula	C38H64N8O14
Molar mass	856.972 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Aurantimycin A is a depsipeptide antibiotic with the molecular formula C₃₈H₆₄N₈O₁₄. ^{[2] [1]} Aurantimycin A is produced by the bacterium Streptomyces aurantiacus . ^{[3] [4]} Aurantimycin A shows cytotoxic properties. ^[5]

References

1. "Aurantimycin A". Pubchem.ncbi.NLM.nih.gov.
2. "Aurantimycin A, Depsipeptide antibiotic (CAS 162478-50-4) (ab144195) | Abcam". www.abcam.com.
3. Grigoriev, P.; Schlegel, R.; Dornberger, K.; Gräfe, U. (1 February 1995). "Formation of membrane pores by aurantimycins A and B, new lipopeptide antibiotics from Streptomyces aurantiacus". Bioelectrochemistry and Bioenergetics. 36 (1): 57–59. doi:10.1016/0302-4598(94)01721-C. ISSN   0302-4598.
4. Kolar, Patrik; Tišler, Miha (28 October 1999). "Recent Advances in the Chemistry of Pyridazines". Advances in Heterocyclic Chemistry Volume 75. Vol. 75. Academic Press. p. 170. doi:10.1016/S0065-2725(08)60985-X. ISBN   978-0-08-057661-9.
5. Bycroft, Barrie W.; Payne, David J. (9 August 2013). Dictionary of Antibiotics and Related Substances: with CD-ROM, Second Edition. CRC Press. p. 303. ISBN   978-1-4822-8215-3.

Further reading

• Gräfe, U.; Schlegel, R.; Ritzau, M.; Ihn, W.; Dornberger, K.; Stengel, C.; Fleck, W. F.; Gutsche, W.; Härtl, A.; Paulus, E. F. (1995). "Aurantimycins, New Depsipeptide Antibiotics from Streptomyces aurantiacus IMET 43917 Production, Isolation, Structure Elucidation, and Biological Activity". The Journal of Antibiotics. 48 (2): 119–125. doi: 10.7164/antibiotics.48.119 . PMID   7706121.
• Hauf, Samuel; Herrmann, Jennifer; Miethke, Marcus; Gibhardt, Johannes; Commichau, Fabian M.; Müller, Rolf; Fuchs, Stephan; Halbedel, Sven (April 2019). "Aurantimycin resistance genes contribute to survival of Listeria monocytogenes during life in the environment". Molecular Microbiology. 111 (4): 1009–1024. doi: 10.1111/mmi.14205 . hdl: 10033/621694 . PMID   30648305.
• Schlegel, R.; Ritzau, M.; Ihn, W.; Stengel, C.; Gräfe, U. (May 1995). "Aurantimycin D, A Shunt Metabolite of Aurantimycin Biosynthesis by Streptomyces aurantiacus IMET 43917". Natural Product Letters. 6 (3): 171–176. doi:10.1080/10575639508043154.