Lankamycin

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

MedKoo CAT#: 598298

CAS#: 30042-37-6

Description: Lankamycin is a macrolide antibiotic isolated from various strains of Streptomyces. Lankamycin may have significant activity against some Gram positive bacteria.


Price and Availability

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Lankamycin 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#: 598298
Name: Lankamycin
CAS#: 30042-37-6
Chemical Formula: C42H72O16
Exact Mass: 832.482
Molecular Weight: 833.02
Elemental Analysis: C, 60.56; H, 8.71; O, 30.73


Synonym: Lankamycin; Kujimycin B; A-20338-N2; A 20338-N2; A20338-N2; Antibiotic A-20338-N2;

IUPAC/Chemical Name: (2R,3S,4S,5R,7S,9S,10S,11R,12S,13R)-12-(((2R,4R,5R,6S)-5-acetoxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-7-hydroxy-10-(((2S,3R,4S,6R)-3-hydroxy-4-methoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-2-((2S,3S)-3-hydroxybutan-2-yl)-3,5,7,9,11,13-hexamethyl-6,14-dioxooxacyclotetradecan-4-yl acetate

InChi Key: JQMACDQCTNFQMM-QAOHEUSVSA-N

InChi Code: InChI=1S/C42H72O16/c1-19-17-41(12,49)37(47)24(6)35(54-28(10)44)23(5)34(21(3)26(8)43)57-39(48)25(7)36(22(4)33(19)58-40-32(46)30(50-14)16-20(2)52-40)56-31-18-42(13,51-15)38(27(9)53-31)55-29(11)45/h19-27,30-36,38,40,43,46,49H,16-18H2,1-15H3/t19-,20+,21-,22+,23-,24+,25+,26-,27-,30-,31-,32+,33-,34+,35-,36-,38+,40-,41-,42+/m0/s1

SMILES Code: CO[C@H]1C[C@H](O[C@H]([C@@H]1O)O[C@H]2[C@H](C[C@](O)(C([C@@H]([C@H]([C@H]([C@@H]([C@H]([C@@H](O)C)C)OC([C@@H]([C@H]([C@@H]2C)O[C@H]3C[C@@](OC)([C@@H]([C@@H](O3)C)OC(C)=O)C)C)=O)C)OC(C)=O)C)=O)C)C)C


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: 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.

2: 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.

3: 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.

4: Suzuki T, Mochizuki S, Yamamoto S, Arakawa K, Kinashi H. Regulation of lankamycin biosynthesis in Streptomyces rochei by two SARP genes, srrY and srrZ. Biosci Biotechnol Biochem. 2010;74(4):819-27. Epub 2010 Apr 7. PubMed PMID: 20378964.

5: Yamamoto S, He Y, Arakawa K, Kinashi H. Gamma-butyrolactone-dependent expression of the Streptomyces antibiotic regulatory protein gene srrY plays a central role in the regulatory cascade leading to lankacidin and lankamycin production in Streptomyces rochei. J Bacteriol. 2008 Feb;190(4):1308-16. Epub 2007 Dec 14. PubMed PMID: 18083808; PubMed Central PMCID: PMC2238197.

6: Ju J, Goo YM. 8-Deoxylankolide from a lankamycin producing Streptomyces spp. J Antibiot (Tokyo). 1997 Aug;50(8):690-2. PubMed PMID: 9315083.

7: Raimundo BC, Heathcock CH. Synthesis of a model for C7-C13 of lankamycin. Org Lett. 2000 Jan;2(1):27-8. PubMed PMID: 10814237.

8: Arakawa K, Mochizuki S, Yamada K, Noma T, Kinashi H. gamma-Butyrolactone autoregulator-receptor system involved in lankacidin and lankamycin production and morphological differentiation in Streptomyces rochei. Microbiology. 2007 Jun;153(Pt 6):1817-27. PubMed PMID: 17526839.

9: Arakawa K, Kodama K, Tatsuno S, Ide S, Kinashi H. Analysis of the loading and hydroxylation steps in lankamycin biosynthesis in Streptomyces rochei. Antimicrob Agents Chemother. 2006 Jun;50(6):1946-52. PubMed PMID: 16723550; PubMed Central PMCID: PMC1479134.

10: Egan RS, Martin JR. Structure of lankamycin. J Am Chem Soc. 1970 Jul 1;92(13):4129-30. PubMed PMID: 5419050.

11: Martin JR, Egan RS, Goldstein AW, Mueller SL, Keller-Schierlein W, Mitscher LA, Foltz RL. 3'-de-o-methyl-2', 3'-anhydro-lankamycin, a new macrolide antibiotic from Streptomyces violaceoniger. Helv Chim Acta. 1976 Jun 14;59(5):1886-94. PubMed PMID: 931757.

12: Goldstein AW, Egan RS, Mueller SL, Martin JR, Keller-Schierlein W. Biotransformation of lankamycin, darcanolide, and 11-acetyllankolide by a blocked mutant of the erythromcyin producing organism Streptomyces erythreus. J Antibiot (Tokyo). 1978 Jan;31(1):63-9. PubMed PMID: 627524.

13: Martin JR, Egan RS, Goldstein AW, Stanaszek RS, Tadanier J, Keller-Schieriein W. Minor lankamycin-related antibiotics from Streptomyces violaceoniger. Helv Chim Acta. 1977 Dec 14;60(8):2559-65. PubMed PMID: 599041.

14: Muntwyler R, Keller-Schierlein W. [Metabolic products of microorganisms. Stereochemistry of lankamycin]. Helv Chim Acta. 1972 Mar 10;55(2):460-7. German. PubMed PMID: 5023148.

15: Mochizuki S, Hiratsu K, Suwa M, Ishii T, Sugino F, Yamada K, Kinashi H. The large linear plasmid pSLA2-L of Streptomyces rochei has an unusually condensed gene organization for secondary metabolism. Mol Microbiol. 2003 Jun;48(6):1501-10. PubMed PMID: 12791134.

16: Quirós LM, Carbajo RJ, Braña AF, Salas JA. Glycosylation of macrolide antibiotics. Purification and kinetic studies of a macrolide glycosyltransferase from Streptomyces antibioticus. J Biol Chem. 2000 Apr 21;275(16):11713-20. PubMed PMID: 10766792.

17: Auerbach T, Mermershtain I, Davidovich C, Bashan A, Belousoff M, Wekselman I, Zimmerman E, Xiong L, Klepacki D, Arakawa K, Kinashi H, Mankin AS, Yonath A. The structure of ribosome-lankacidin complex reveals ribosomal sites for synergistic antibiotics. Proc Natl Acad Sci U S A. 2010 Feb 2;107(5):1983-8. doi: 10.1073/pnas.0914100107. Epub 2010 Jan 11. PubMed PMID: 20080686; PubMed Central PMCID: PMC2804743.

18: Kinashi H, Mori E, Hatani A, Nimi O. Isolation and characterization of linear plasmids from lankacidin-producing Streptomyces species. J Antibiot (Tokyo). 1994 Dec;47(12):1447-55. PubMed PMID: 7844039.

19: 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.

20: 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.