Lankacidin C 8-acetate

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 598297

CAS#: 23812-97-7

Description: Lankacidin C 8-acetate is a lankacidin-group (T-2636) antibiotic.


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Lankacidin C 8-acetate is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 598297
Name: Lankacidin C 8-acetate
CAS#: 23812-97-7
Chemical Formula: C27H35NO8
Exact Mass: 501.2363
Molecular Weight: 501.57
Elemental Analysis: C, 64.66; H, 7.03; N, 2.79; O, 25.52


Synonym: Lankacidin C 8-acetate; 5-18-12-00134 (Beilstein Handbook Reference);

IUPAC/Chemical Name: (1S,2R,3E,5E,7S,9E,11E,13S,15R,19R)-13-hydroxy-1,4,10,19-tetramethyl-17,18-dioxo-2-(2-oxopropanamido)-16-oxabicyclo[13.2.2]nonadeca-3,5,9,11-tetraen-7-yl acetate

InChi Key: SXLMQJVXWZFRNQ-LDACTNBVSA-N

InChi Code: InChI=1S/C27H35NO8/c1-15-7-10-20(31)14-22-17(3)24(32)27(6,26(34)36-22)23(28-25(33)18(4)29)13-16(2)9-12-21(11-8-15)35-19(5)30/h7-10,12-13,17,20-23,31H,11,14H2,1-6H3,(H,28,33)/b10-7+,12-9+,15-8+,16-13+/t17-,20-,21+,22-,23-,27+/m1/s1

SMILES Code: CC(C(N[C@H](/C=C(C)/C=C/[C@@H](OC(C)=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)=O


Technical Data

Appearance:
Solid powder

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).

Harmonized System Code:
2934.99.03.00


References

1: Nakahama K, Harada S, Igarasi S. Studies on lankacidin-group (T-2636) antibiotics. X. Microbial conversion of lankacidin-group antibiotics. J Antibiot (Tokyo). 1975 May;28(5):390-4. PubMed PMID: 240790.

2: Arakawa K. Genetic and biochemical analysis of the antibiotic biosynthetic gene clusters on the Streptomyces linear plasmid. Biosci Biotechnol Biochem. 2014;78(2):183-9. doi: 10.1080/09168451.2014.882761. Epub 2014 Apr 16. Review. PubMed PMID: 25036669.

3: Hatano K, Harada S, Kishi T. Studies on lankacidin-group (T-2636) ANTIBIOTICS. IX Preparation of C-labeled lankacidin C 14-propionate. J Antibiot (Tokyo). 1975 Jan;28(1):15-20. PubMed PMID: 1126865.

4: 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.

5: Harada S, Tanayama S, Kishi T. Studies on lankacidin-group (T-2636) antibiotics. 8. Metabolism of lankacidin C 14-propionate in rats and mice. J Antibiot (Tokyo). 1973 Nov;26(11):658-68. PubMed PMID: 4792113.

6: Arakawa K, Tsuda N, Taniguchi A, Kinashi H. The butenolide signaling molecules SRB1 and SRB2 induce lankacidin and lankamycin production in Streptomyces rochei. Chembiochem. 2012 Jul 9;13(10):1447-57. doi: 10.1002/cbic.201200149. Epub 2012 Jun 14. PubMed PMID: 22761035.

7: Belousoff MJ, Shapira T, Bashan A, Zimmerman E, Rozenberg H, Arakawa K, Kinashi H, Yonath A. Crystal structure of the synergistic antibiotic pair, lankamycin and lankacidin, in complex with the large ribosomal subunit. Proc Natl Acad Sci U S A. 2011 Feb 15;108(7):2717-22. doi: 10.1073/pnas.1019406108. Epub 2011 Jan 31. PubMed PMID: 21282615; PubMed Central PMCID: PMC3041097.

8: Kunitake H, Hiramatsu T, Kinashi H, Arakawa K. Isolation and Biosynthesis of an Azoxyalkene Compound Produced by a Multiple Gene Disruptant of Streptomyces rochei. Chembiochem. 2015 Oct 12;16(15):2237-43. doi: 10.1002/cbic.201500393. Epub 2015 Sep 2. PubMed PMID: 26300120.

9: Sawada H, Suzuki T, Akiyama S, Nakao Y. Mechanism of the stimulatory effect of cyclodextrins on lankacidin-producing Streptomyces. Appl Microbiol Biotechnol. 1990 Feb;32(5):556-9. PubMed PMID: 1366439.

10: Williams DR, Rojas CM, Bogen SL. Studies of Acyl Nitrene Insertions. A Stereocontrolled Route toward Lankacidin Antibiotics. J Org Chem. 1999 Feb 5;64(3):736-746. PubMed PMID: 11674141.

11: Tatsuno S, Arakawa K, Kinashi H. Extensive mutational analysis of modular-iterative mixed polyketide biosynthesis of lankacidin in Streptomyces rochei. Biosci Biotechnol Biochem. 2009 Dec;73(12):2712-9. Epub 2009 Dec 7. PubMed PMID: 19966473.

12: Cao Z, Yoshida R, Kinashi H, Arakawa K. Blockage of the early step of lankacidin biosynthesis caused a large production of pentamycin, citreodiol and epi-citreodiol in Streptomyces rochei. J Antibiot (Tokyo). 2015 May;68(5):328-33. doi: 10.1038/ja.2014.160. Epub 2014 Dec 3. PubMed PMID: 25464973.

13: Omura S, Nakagawa A, Fujimoto T, Saito K, Otoguro K, Walsh JC. Hygromycin A, an antitreponemal substance. I. Screening method and therapeutic effect for Treponema hyodysenteriae-caused infection in CF-1 mice. J Antibiot (Tokyo). 1987 Nov;40(11):1619-26. PubMed PMID: 3693130.

14: Kikuchi M, Nakao Y. Mode of action of the protein, SP127, which enhances the activity of macrolide antibiotics against Pseudomonas aeruginosa. J Antibiot (Tokyo). 1977 Mar;30(3):215-20. PubMed PMID: 405356.

15: 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.

16: 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.