Synonym
Okilactomycin; YP-02908L-A; YP 02908L-A; YP02908L-A.
IUPAC/Chemical Name
3,5-Ethano-2H-furo(2,3-o)(2)benzoxacycloundecin-13-carboxylic acid, 3,3a,5,6,7,8,9,10,11,11a,14,15-dodecahydro-2,17-dioxo-16-methylene-3,6,8,14-tetramethyl-, (3R-(3R*,3aR*,5R*,6R*,8R*,11aS*,14S*,15aS*))-
InChi Key
KQZIMLFKBWIOJJ-ZRHSTDQJSA-N
InChi Code
InChI=1S/C24H32O6/c1-12-7-6-8-16-10-17(20(26)27)14(3)11-24(16)21-23(5,22(28)30-24)19(25)15(4)18(29-21)13(2)9-12/h10,12-14,16,18,21H,4,6-9,11H2,1-3,5H3,(H,26,27)/t12-,13-,14+,16+,18-,21-,23+,24+/m1/s1
SMILES Code
O=C(C1=C[C@]2([H])CCC[C@@H](C)C[C@@H](C)[C@@]3([H])O[C@@]4([H])[C@]2(OC([C@@]4(C)C(C3=C)=O)=O)C[C@@H]1C)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
>2 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
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
416.51
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: Niu D, Hoye TR. A concise total synthesis of (±)- and (-)-okilactomycin D. Org Lett. 2012 Feb 3;14(3):828-31. doi: 10.1021/ol203355g. Epub 2012 Jan 24. PubMed PMID: 22273402; PubMed Central PMCID: PMC3272355.
2: Tenenbaum JM, Morris WJ, Custar DW, Scheidt KA. Synthesis of (-)-okilactomycin by a Prins-type fragment-assembly strategy. Angew Chem Int Ed Engl. 2011 Jun 20;50(26):5892-5. doi: 10.1002/anie.201102037. Epub 2011 May 10. PubMed PMID: 21560215; PubMed Central PMCID: PMC3219920.
3: Smith AB 3rd, Bosanac T, Basu K. Evolution of the total synthesis of (-)-okilactomycin exploiting a tandem oxy-cope rearrangement/oxidation, a Petasis-Ferrier union/rearrangement, and ring-closing metathesis. J Am Chem Soc. 2009 Feb 18;131(6):2348-58. doi: 10.1021/ja8084669. PubMed PMID: 19170499; PubMed Central PMCID: PMC2697663.
4: Zhang C, Ondeyka JG, Zink DL, Basilio A, Vicente F, Salazar O, Genilloud O, Dorso K, Motyl M, Byrne K, Singh SB. Discovery of okilactomycin and congeners from Streptomyces scabrisporus by antisense differential sensitivity assay targeting ribosomal protein S4. J Antibiot (Tokyo). 2009 Feb;62(2):55-61. doi: 10.1038/ja.2008.8. Epub 2009 Jan 9. PubMed PMID: 19132063.
5: Smith AB 3rd, Fox RJ, Razler TM. Evolution of the Petasis-Ferrier union/rearrangement tactic: construction of architecturally complex natural products possessing the ubiquitous cis-2,6-substituted tetrahydropyran structural element. Acc Chem Res. 2008 May;41(5):675-87. doi: 10.1021/ar700234r. PubMed PMID: 18489082.
6: Smith AB 3rd, Basu K, Bosanac T. Total synthesis of (-)-okilactomycin. J Am Chem Soc. 2007 Dec 5;129(48):14872-4. Epub 2007 Nov 13. PubMed PMID: 17997560.
7: Imai H, Nakagawa A, Omura S. Biosynthesis of the antibiotic okilactomycin. J Antibiot (Tokyo). 1989 Aug;42(8):1321-3. PubMed PMID: 2759916.
8: Imai H, Kaniwa H, Tokunaga T, Fujita S, Furuya T, Matsumoto H, Shimizu M. Okilactomycin, a novel antibiotic produced by a Streptomyces species. II. Structure determination. J Antibiot (Tokyo). 1987 Nov;40(11):1483-9. PubMed PMID: 3693117.
9: Imai H, Suzuki K, Morioka M, Numasaki Y, Kadota S, Nagai K, Sato T, Iwanami M, Saito T. Okilactomycin, a novel antibiotic produced by a Streptomyces species. I. Taxonomy, fermentation, isolation and characterization. J Antibiot (Tokyo). 1987 Nov;40(11):1475-82. PubMed PMID: 3693116.
