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

MedKoo CAT#: 561189

CAS#: 65101-87-3

Description: Nanchangmycin is a polyether antibiotic that acts against a broad spectrum of harmful nematodes and insects.


Price and Availability

Size
Price

5mg
USD 320
Size
Price

10mg
USD 560
Size
Price

25mg
USD 1100

Nanchangmycin, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 561189
Name: Nanchangmycin
CAS#: 65101-87-3
Chemical Formula: C47H77NaO14
Exact Mass:
Molecular Weight: 889.1088
Elemental Analysis: C, 63.49; H, 8.73; Na, 2.59; O, 25.19


Synonym: Nanchangmycin; CCRIS 8440; CCRIS-8440; CCRIS8440; Nanchangmycin A

IUPAC/Chemical Name: Sodium (E,2S,4R,8S)-8-[(2S,5R,7S,8R,9R)-7-hydroxy-2-[(2R,4S,5S,7R,9S,10R)-2-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-9-[(5S,6R)-5-methoxy-6-methyloxan-2-yl]oxy-4,10-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2,4,6-trimethyl-5-oxonon-6-enoate

InChi Key: XMAIRYYXDCNFKP-DYTQFKGPSA-M

InChi Code: InChI=1S/C47H78O14.Na/c1-24(40(50)25(2)18-28(5)43(51)52)17-26(3)41-31(8)34(49)22-45(59-41)16-15-44(11,61-45)38-21-36(56-39-14-13-35(54-12)33(10)55-39)32(9)47(58-38)30(7)20-37(57-47)42-27(4)19-29(6)46(53,23-48)60-42;/h17,25-39,41-42,48-49,53H,13-16,18-23H2,1-12H3,(H,51,52);/q;+1/p-1/b24-17+;/t25-,26+,27+,28+,29-,30+,31-,32-,33-,34+,35+,36+,37-,38-,39?,41-,42+,44+,45-,46+,47+;/m1./s1

SMILES Code: C[C@H]([C@@H](O1)[C@H](C)[C@@H](O)C[C@@]21CC[C@@](C)([C@@H](C[C@H](OC3O[C@H](C)[C@@H](OC)CC3)[C@H]4C)O[C@]54[C@@H](C)C[C@H]([C@H]6O[C@](CO)(O)[C@H](C)C[C@@H]6C)O5)O2)/C=C(C)/C([C@H](C)C[C@H](C)C([O-])=O)=O.[Na+]


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:
>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).

Harmonized System Code:
293490


References

1: Guo X, Liu T, Deng Z, Cane DE. Essential role of the donor acyl carrier protein in stereoselective chain translocation to a fully reducing module of the nanchangmycin polyketide synthase. Biochemistry. 2012 Jan 31;51(4):879-87. doi: 10.1021/bi201768v. Epub 2012 Jan 17. PubMed PMID: 22229794; PubMed Central PMCID: PMC3273620.

2: Yu Q, Du A, Liu T, Deng Z, He X. The biosynthesis of the polyether antibiotic nanchangmycin is controlled by two pathway-specific transcriptional activators. Arch Microbiol. 2012 Jun;194(6):415-26. doi: 10.1007/s00203-011-0768-8. Epub 2011 Nov 23. PubMed PMID: 22109812.

3: Zhang J, An J, Wang JJ, Yan YJ, He HR, Wang XJ, Xiang WS. Genetic engineering of Streptomyces bingchenggensis to produce milbemycins A3/A4 as main components and eliminate the biosynthesis of nanchangmycin. Appl Microbiol Biotechnol. 2013 Dec;97(23):10091-101. Epub 2013 Sep 29. PubMed PMID: 24077727.

4: Liu T, Lin X, Zhou X, Deng Z, Cane DE. Mechanism of thioesterase-catalyzed chain release in the biosynthesis of the polyether antibiotic nanchangmycin. Chem Biol. 2008 May;15(5):449-58. doi: 10.1016/j.chembiol.2008.04.006. PubMed PMID: 18482697; PubMed Central PMCID: PMC2426748.

5: Liu T, You D, Valenzano C, Sun Y, Li J, Yu Q, Zhou X, Cane DE, Deng Z. Identification of NanE as the thioesterase for polyether chain release in nanchangmycin biosynthesis. Chem Biol. 2006 Sep;13(9):945-55. PubMed PMID: 16984884.

6: Guo X, Liu T, Valenzano CR, Deng Z, Cane DE. Mechanism and stereospecificity of a fully saturating polyketide synthase module: nanchangmycin synthase module 2 and its dehydratase domain. J Am Chem Soc. 2010 Oct 27;132(42):14694-6. doi: 10.1021/ja1073432. PubMed PMID: 20925339; PubMed Central PMCID: PMC2959152.

7: Sun Y, Zhou X, Dong H, Tu G, Wang M, Wang B, Deng Z. A complete gene cluster from Streptomyces nanchangensis NS3226 encoding biosynthesis of the polyether ionophore nanchangmycin. Chem Biol. 2003 May;10(5):431-41. PubMed PMID: 12770825.

8: Sun YH, Zhou XF, Tu GQ, Deng ZX. [Determination of nanchangmycin and meilingmycin by high performance liquid chromatography]. Se Pu. 2002 Jan;20(1):43-5. Chinese. PubMed PMID: 12541617.

9: Sun Y, Zhou X, Liu J, Bao K, Zhang G, Tu G, Kieser T, Deng Z. 'Streptomyces nanchangensis', a producer of the insecticidal polyether antibiotic nanchangmycin and the antiparasitic macrolide meilingmycin, contains multiple polyketide gene clusters. Microbiology. 2002 Feb;148(Pt 2):361-71. PubMed PMID: 11832500.

10: Wang XJ, Zhang B, Yan YJ, An J, Zhang J, Liu CX, Xiang WS. Characterization and analysis of an industrial strain of Streptomyces bingchenggensis by genome sequencing and gene microarray. Genome. 2013 Nov;56(11):677-89. doi: 10.1139/gen-2013-0098. PubMed PMID: 24299107.

11: Rausch K, Hackett BA, Weinbren NL, Reeder SM, Sadovsky Y, Hunter CA, Schultz DC, Coyne CB, Cherry S. Screening Bioactives Reveals Nanchangmycin as a Broad Spectrum Antiviral Active against Zika Virus. Cell Rep. 2017 Jan 17;18(3):804-815. doi: 10.1016/j.celrep.2016.12.068. PubMed PMID: 28099856; PubMed Central PMCID: PMC5270376.

12: Wang XJ, Yan YJ, Zhang B, An J, Wang JJ, Tian J, Jiang L, Chen YH, Huang SX, Yin M, Zhang J, Gao AL, Liu CX, Zhu ZX, Xiang WS. Genome sequence of the milbemycin-producing bacterium Streptomyces bingchenggensis. J Bacteriol. 2010 Sep;192(17):4526-7. doi: 10.1128/JB.00596-10. Epub 2010 Jun 25. PubMed PMID: 20581206; PubMed Central PMCID: PMC2937363.

13: Harvey BM, Mironenko T, Sun Y, Hong H, Deng Z, Leadlay PF, Weissman KJ, Haydock SF. Insights into polyether biosynthesis from analysis of the nigericin biosynthetic gene cluster in Streptomyces sp. DSM4137. Chem Biol. 2007 Jun;14(6):703-14. PubMed PMID: 17584617.

14: Wang XJ, Guo SL, Guo WQ, Xi D, Xiang WS. Role of nsdA in negative regulation of antibiotic production and morphological differentiation in Streptomyces bingchengensis. J Antibiot (Tokyo). 2009 Jun;62(6):309-13. doi: 10.1038/ja.2009.33. Epub 2009 May 15. PubMed PMID: 19444300.

15: Xie X, Garg A, Khosla C, Cane DE. Mechanism and Stereochemistry of Polyketide Chain Elongation and Methyl Group Epimerization in Polyether Biosynthesis. J Am Chem Soc. 2017 Mar 1;139(8):3283-3292. doi: 10.1021/jacs.7b00278. Epub 2017 Feb 14. PubMed PMID: 28157306; PubMed Central PMCID: PMC5332327.

16: Xie X, Garg A, Khosla C, Cane DE. Elucidation of the Cryptic Methyl Group Epimerase Activity of Dehydratase Domains from Modular Polyketide Synthases Using a Tandem Modules Epimerase Assay. J Am Chem Soc. 2017 Jul 19;139(28):9507-9510. doi: 10.1021/jacs.7b05502. Epub 2017 Jul 7. PubMed PMID: 28682630.

17: Liu X, Xie S, Ni T, Chen D, Wang X, Pan Y, Wang Y, Huang L, Cheng G, Qu W, Liu Z, Tao Y, Yuan Z. Magnetic solid-phase extraction based on carbon nanotubes for the determination of polyether antibiotic and s-triazine drug residues in animal food with LC-MS/MS. J Sep Sci. 2017 Jun;40(11):2416-2430. doi: 10.1002/jssc.201700017. Epub 2017 May 4. PubMed PMID: 28402029.