Synonym
Lankacidinol; T-2636 F; T 2636 F; T2636 F; Antibiotic T 2636F;
IUPAC/Chemical Name
(R)-N-((1S,2R,3E,5E,7S,9E,11E,13S,15R,19R)-7,13-dihydroxy-1,4,10,19-tetramethyl-17,18-dioxo-16-oxabicyclo[13.2.2]nonadeca-3,5,9,11-tetraen-2-yl)-2-hydroxypropanamide
InChi Key
FUDDPCATVZFGCZ-SQFDTGPGSA-N
InChi Code
InChI=1S/C25H35NO7/c1-14-6-9-18(28)10-8-15(2)12-21(26-23(31)17(4)27)25(5)22(30)16(3)20(33-24(25)32)13-19(29)11-7-14/h6-8,10-12,16-21,27-29H,9,13H2,1-5H3,(H,26,31)/b10-8+,11-7+,14-6+,15-12+/t16-,17-,18+,19-,20-,21-,25+/m1/s1
SMILES Code
O[C@H](C)C(N[C@H](/C=C(C)/C=C/[C@@H](O)C/C=C(C)/C=C/[C@@H](O)C[C@@]1([H])O2)[C@](C([C@@H]1C)=O)(C)C2=O)=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
>3 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
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
461.55
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: Oostu K, Matsumoto T, Harada S, Kishi T. Antitumor and immunosuppressive activities of lankacidin-group antibiotics: structure-activity relationships. Cancer Chemother Rep. 1975 Sep-Oct;59(5):919-28. PubMed PMID: 1148.
2: Hayashi T, Okada J, Kondo S, Yamazaki T. Role of intestinal excretion in the effect of subcutaneously administered sedecamycin on cecal infection caused by Treponema hyodysenteriae in mice. Antimicrob Agents Chemother. 1991 Aug;35(8):1601-4. PubMed PMID: 1929332; PubMed Central PMCID: PMC245226.
3: Okada J, Kondo S. Liquid chromatographic method for determining the macrolide antibiotic sedecamycin and its major metabolites in swine plasma and tissues. J Assoc Off Anal Chem. 1987 Sep-Oct;70(5):818-24. PubMed PMID: 3680117.
4: Tatsuno S, Arakawa K, Kinashi H. Analysis of modular-iterative mixed biosynthesis of lankacidin by heterologous expression and gene fusion. J Antibiot (Tokyo). 2007 Nov;60(11):700-8. PubMed PMID: 18057700.
5: McFarland JW, Pirie DK, Retsema JA, English AR. Side chain modifications in lankacidin group antibiotics. Antimicrob Agents Chemother. 1984 Feb;25(2):226-33. PubMed PMID: 6370129; PubMed Central PMCID: PMC185479.
6: Yamauchi Y, Nindita Y, Hara K, Umeshiro A, Yabuuchi Y, Suzuki T, Kinashi H, Arakawa K. Quinoprotein dehydrogenase functions at the final oxidation step of lankacidin biosynthesis in Streptomyces rochei 7434AN4. J Biosci Bioeng. 2018 Jun 2. pii: S1389-1723(18)30057-4. doi: 10.1016/j.jbiosc.2018.03.006. [Epub ahead of print] PubMed PMID: 29871824.
7: Zheng K, Shen D, Hong R. Biomimetic Synthesis of Lankacidin Antibiotics. J Am Chem Soc. 2017 Sep 20;139(37):12939-12942. doi: 10.1021/jacs.7b08500. Epub 2017 Sep 6. PubMed PMID: 28853876.
8: Lu C, Li JM, Qi H, Zhang H, Zhang J, Xiang WS, Wang JD, Wang XJ. Two new lankacidin-related metabolites from Streptomyces sp. HS-NF-1178. J Antibiot (Tokyo). 2018 Mar;71(3):397-401. doi: 10.1038/s41429-017-0004-0. Epub 2018 Jan 18. PubMed PMID: 29348529.
