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MedKoo Cat#: 527488 | Name: Nikkomycin Z

Description:

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

Nikkomycin Z is a competitive inhibitor of chitin synthase and inhibitor of the growth of filamentous fungi, insects, acarids and yeasts.

Chemical Structure

Nikkomycin Z
CAS#59456-70-1 (free base)

Theoretical Analysis

MedKoo Cat#: 527488

Name: Nikkomycin Z

CAS#: 59456-70-1 (free base)

Chemical Formula: C20H25N5O10

Exact Mass: 495.1601

Molecular Weight: 495.45

Elemental Analysis: C, 48.49; H, 5.09; N, 14.14; O, 32.29

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
59456-70-1 (free base) Nikkomycin Z (HCl)
Synonym
Nikkomycin Z
IUPAC/Chemical Name
(2R)-2-[[(2S,3S,4S)-2-Amino-4-hydroxy-4-(5-hydroxypyridin-2-yl)-3-methylbutanoyl]amino]-2-[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid
InChi Key
WWJFFVUVFNBJTN-JKEIIPFCSA-N
InChi Code
InChI=1S/C20H25N5O10/c1-7(13(28)9-3-2-8(26)6-22-9)11(21)17(31)24-12(19(32)33)16-14(29)15(30)18(35-16)25-5-4-10(27)23-20(25)34/h2-7,11-16,18,26,28-30H,21H2,1H3,(H,24,31)(H,32,33)(H,23,27,34)/t7-,11-,12+,13-,14-,15+,16+,18+/m0/s1
SMILES Code
O=C(O)[C@H](NC([C@@H](N)[C@H](C)[C@H](O)C1=NC=C(O)C=C1)=O)[C@H]2O[C@@H](N(C(N3)=O)C=CC3=O)[C@H](O)[C@@H]2O
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).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 495.45 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.

Recalculate based on batch purity %
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: Xu J, Zhang J, Zhuo J, Li Y, Tian Y, Tan H. Activation and mechanism of a cryptic oviedomycin gene cluster via the disruption of a global regulatory gene, adpA, in Streptomyces ansochromogenes. J Biol Chem. 2017 Dec 1;292(48):19708-19720. doi: 10.1074/jbc.M117.809145. Epub 2017 Sep 25. PubMed PMID: 28972184; PubMed Central PMCID: PMC5712612. 2: Healey KR, Nagasaki Y, Zimmerman M, Kordalewska M, Park S, Zhao Y, Perlin DS. The Gastrointestinal Tract Is a Major Source of Echinocandin Drug Resistance in a Murine Model of Candida glabrata Colonization and Systemic Dissemination. Antimicrob Agents Chemother. 2017 Nov 22;61(12). pii: e01412-17. doi: 10.1128/AAC.01412-17. Print 2017 Dec. PubMed PMID: 28971865; PubMed Central PMCID: PMC5700336. 3: Zhuo J, Ma B, Xu J, Hu W, Zhang J, Tan H, Tian Y. Reconstruction of a hybrid nucleoside antibiotic gene cluster based on scarless modification of large DNA fragments. Sci China Life Sci. 2017 Sep;60(9):968-979. doi: 10.1007/s11427-017-9119-1. Epub 2017 Aug 21. PubMed PMID: 28840532. 4: Cheung YY, Hui M. Effects of Echinocandins in Combination with Nikkomycin Z against Invasive Candida albicans Bloodstream Isolates and the fks Mutants. Antimicrob Agents Chemother. 2017 Oct 24;61(11). pii: e00619-17. doi: 10.1128/AAC.00619-17. Print 2017 Nov. PubMed PMID: 28827418; PubMed Central PMCID: PMC5655089. 5: He N, Wu P, Lei Y, Xu B, Zhu X, Xu G, Gao Y, Qi J, Deng Z, Tang G, Chen W, Xiao Y. Construction of an octosyl acid backbone catalyzed by a radical S-adenosylmethionine enzyme and a phosphatase in the biosynthesis of high-carbon sugar nucleoside antibiotics. Chem Sci. 2017 Jan 1;8(1):444-451. doi: 10.1039/c6sc01826b. Epub 2016 Aug 19. PubMed PMID: 28451191; PubMed Central PMCID: PMC5365060. 6: Wise CE, Makris TM. Recruitment and Regulation of the Non-ribosomal Peptide Synthetase Modifying Cytochrome P450 Involved in Nikkomycin Biosynthesis. ACS Chem Biol. 2017 May 19;12(5):1316-1326. doi: 10.1021/acschembio.7b00081. Epub 2017 Mar 28. PubMed PMID: 28300390. 7: Seyedmousavi S, Rafati H, Ilkit M, Tolooe A, Hedayati MT, Verweij P. Systemic Antifungal Agents: Current Status and Projected Future Developments. Methods Mol Biol. 2017;1508:107-139. PubMed PMID: 27837500. 8: Goughenour KD, Rappleye CA. Antifungal therapeutics for dimorphic fungal pathogens. Virulence. 2017 Feb 17;8(2):211-221. doi: 10.1080/21505594.2016.1235653. Epub 2016 Sep 19. PubMed PMID: 27646561; PubMed Central PMCID: PMC5354166. 9: Kottom TJ, Hebrink DM, Jenson PE, Ramirez-Prado JH, Limper AH. Characterization of N-Acetylglucosamine Biosynthesis in Pneumocystis species. A New Potential Target for Therapy. Am J Respir Cell Mol Biol. 2017 Feb;56(2):213-222. doi: 10.1165/rcmb.2016-0155OC. PubMed PMID: 27632412; PubMed Central PMCID: PMC5359649. 10: Vaknin Y, Hillmann F, Iannitti R, Ben Baruch N, Sandovsky-Losica H, Shadkchan Y, Romani L, Brakhage A, Kniemeyer O, Osherov N. Identification and Characterization of a Novel Aspergillus fumigatus Rhomboid Family Putative Protease, RbdA, Involved in Hypoxia Sensing and Virulence. Infect Immun. 2016 May 24;84(6):1866-78. doi: 10.1128/IAI.00011-16. Print 2016 Jun. PubMed PMID: 27068092; PubMed Central PMCID: PMC4907145. 11: Fernandes C, Prados-Rosales R, Silva BM, Nakouzi-Naranjo A, Zuzarte M, Chatterjee S, Stark RE, Casadevall A, Gonçalves T. Activation of Melanin Synthesis in Alternaria infectoria by Antifungal Drugs. Antimicrob Agents Chemother. 2015 Dec 28;60(3):1646-55. doi: 10.1128/AAC.02190-15. PubMed PMID: 26711773; PubMed Central PMCID: PMC4775914. 12: Wang L, Du D, Li J, Tian Y, Liu H, Niu G, Tan H. [Engineering and heterologous expression of a nikkomycin biosynthetic gene cluster]. Wei Sheng Wu Xue Bao. 2015 Jun 4;55(6):707-18. Chinese. PubMed PMID: 26562995. 13: Lu C, Liao G, Zhang J, Tan H. Identification of novel tylosin analogues generated by a wblA disruption mutant of Streptomyces ansochromogenes. Microb Cell Fact. 2015 Nov 2;14:173. doi: 10.1186/s12934-015-0359-5. PubMed PMID: 26525981; PubMed Central PMCID: PMC4630966. 14: Maiti P, Ghorai P, Ghosh S, Kamthan M, Tyagi RK, Datta A. Mapping of functional domains and characterization of the transcription factor Cph1 that mediate morphogenesis in Candida albicans. Fungal Genet Biol. 2015 Oct;83:45-57. doi: 10.1016/j.fgb.2015.08.004. Epub 2015 Aug 17. PubMed PMID: 26291891. 15: Walker LA, Lee KK, Munro CA, Gow NA. Caspofungin Treatment of Aspergillus fumigatus Results in ChsG-Dependent Upregulation of Chitin Synthesis and the Formation of Chitin-Rich Microcolonies. Antimicrob Agents Chemother. 2015 Oct;59(10):5932-41. doi: 10.1128/AAC.00862-15. Epub 2015 Jul 13. PubMed PMID: 26169407; PubMed Central PMCID: PMC4576100. 16: Singh V, Praveen V, Tripathi D, Haque S, Somvanshi P, Katti SB, Tripathi CK. Isolation, characterization and antifungal docking studies of wortmannin isolated from Penicillium radicum. Sci Rep. 2015 Jul 10;5:11948. doi: 10.1038/srep11948. PubMed PMID: 26159770; PubMed Central PMCID: PMC4498184. 17: Qi J, Liu J, Wan D, Cai YS, Wang Y, Li S, Wu P, Feng X, Qiu G, Yang SP, Chen W, Deng Z. Metabolic engineering of an industrial polyoxin producer for the targeted overproduction of designer nucleoside antibiotics. Biotechnol Bioeng. 2015 Sep;112(9):1865-71. doi: 10.1002/bit.25594. Epub 2015 May 12. PubMed PMID: 25827606. 18: Choi YK, Kang EH, Park HM. Role of LAMMER Kinase in Cell Wall Biogenesis during Vegetative Growth of Aspergillus nidulans. Mycobiology. 2014 Dec;42(4):422-6. doi: 10.5941/MYCO.2014.42.4.422. Epub 2014 Dec 31. PubMed PMID: 25606019; PubMed Central PMCID: PMC4298851. 19: Niu G, Tan H. Nucleoside antibiotics: biosynthesis, regulation, and biotechnology. Trends Microbiol. 2015 Feb;23(2):110-9. doi: 10.1016/j.tim.2014.10.007. Epub 2014 Nov 13. Review. PubMed PMID: 25468791. 20: Feng C, Ling H, Du D, Zhang J, Niu G, Tan H. Novel nikkomycin analogues generated by mutasynthesis in Streptomyces ansochromogenes. Microb Cell Fact. 2014 Apr 21;13(1):59. doi: 10.1186/1475-2859-13-59. PubMed PMID: 24751325; PubMed Central PMCID: PMC4021061.

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