Synonym
Diffusomycin; Oxazolomycin
IUPAC/Chemical Name
3-Hydroxy-N-(6-hydroxy-9-(8-hydroxy-5,7-dimethyl-1,6-dioxo-2-oxa-5-azaspiro(3.4)oct-8-yl)-9-methoxy-7-methyl-2,4-nonadienyl)-2,2,4-trimethyl-10-(5-oxazolyl)-4,6,8-decatrienamide
InChi Key
ZZNSFVQRQDZGGX-XRDXNDOHSA-N
InChi Code
InChI=1S/C35H49N3O9/c1-23(15-11-8-9-12-16-26-20-36-22-47-26)29(40)33(4,5)31(42)37-18-14-10-13-17-27(39)24(2)19-28(45-7)35(44)25(3)30(41)38(6)34(35)21-46-32(34)43/h8-15,17,20,22,24-25,27-29,39-40,44H,16,18-19,21H2,1-7H3,(H,37,42)/b11-8+,12-9+,14-10+,17-13+,23-15+
SMILES Code
O=C(NC/C=C/C=C/C(O)C(C)CC(C(C1(N2C)COC1=O)(O)C(C)C2=O)OC)C(C)(C)C(O)/C(C)=C/C=C/C=C/CC3=CN=CO3
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
655.79
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: Tonew E, Tonew M, Gräfe U, Zöpel P. On the antiviral activity of diffusomycin (oxazolomycin). Acta Virol. 1992 Mar;36(2):166-72. PMID: 1359768.
2: Eto K, Yoshino M, Takahashi K, Ishihara J, Hatakeyama S. Total synthesis of oxazolomycin A. Org Lett. 2011 Oct 7;13(19):5398-401. doi: 10.1021/ol202306d. Epub 2011 Sep 2. PMID: 21888385.
3: Bagwell CL, Moloney MG, Thompson AL. On the antibiotic activity of oxazolomycin. Bioorg Med Chem Lett. 2008 Jul 15;18(14):4081-6. doi: 10.1016/j.bmcl.2008.05.105. Epub 2008 Jun 14. PMID: 18558487.
4: Koomsiri W, Inahashi Y, Kimura T, Shiomi K, Takahashi Y, Ōmura S, Thamchaipenet A, Nakashima T. Bisoxazolomycin A: a new natural product from 'Streptomyces subflavus subsp. irumaensis' AM-3603. J Antibiot (Tokyo). 2017 Dec;70(12):1142-1145. doi: 10.1038/ja.2017.113. Epub 2017 Sep 27. PMID: 28951599.
5: Angelov P, Chau YK, Fryer PJ, Moloney MG, Thompson AL, Trippier PC. Biomimetic synthesis, antibacterial activity and structure-activity properties of the pyroglutamate core of oxazolomycin. Org Biomol Chem. 2012 May 7;10(17):3472-85. doi: 10.1039/c2ob00042c. Epub 2012 Mar 22. PMID: 22437843.
6: Donohoe TJ, O'Riordan TJ, Peifer M, Jones CR, Miles TJ. Asymmetric synthesis of the fully elaborated pyrrolidinone core of oxazolomycin A. Org Lett. 2012 Nov 2;14(21):5460-3. doi: 10.1021/ol302541j. Epub 2012 Oct 12. PMID: 23061613.
7: Bagwell CL, Moloney MG, Yaqoob M. Oxazolomycins: natural product lead structures for novel antibacterials by click fragment conjugation. Bioorg Med Chem Lett. 2010 Apr 1;20(7):2090-4. doi: 10.1016/j.bmcl.2010.02.066. Epub 2010 Feb 20. PMID: 20223659.
8: Moloney MG, Trippier PC, Yaqoob M, Wang Z. The oxazolomycins: a structurally novel class of bioactive compounds. Curr Drug Discov Technol. 2004 Oct;1(3):181-99. doi: 10.2174/1570163043334974. PMID: 16472256.
9: Dorrestein PC, Van Lanen SG, Li W, Zhao C, Deng Z, Shen B, Kelleher NL. The bifunctional glyceryl transferase/phosphatase OzmB belonging to the HAD superfamily that diverts 1,3-bisphosphoglycerate into polyketide biosynthesis. J Am Chem Soc. 2006 Aug 16;128(32):10386-7. doi: 10.1021/ja0639362. PMID: 16895402.
10: Bulger PG, Moloney MG, Trippier PC. A multicomponent coupling strategy suitable for the synthesis of the triene component of the oxazolomycin antibiotics. Org Biomol Chem. 2003 Nov 7;1(21):3726-37. doi: 10.1039/b306925g. PMID: 14649904.
