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Nikkomycin Z from Streptomyces tendae - ≥90% (HPLC), high purity , CAS No.59456-70-1

≥90%(HPLC)

CAS#: 59456-70-1
Formula: C₂₀H₂₅N₅O₁₀
Molecular Weight: 495.44
MDL number: MFCD00869648
PubChem CID: 456557

Item Number

N463180

Grouped product items
SKU	Size	Availability	Price	Qty
N463180-1mg	1mg	Available within 8-12 weeks(?) Production requires sourcing of materials. We appreciate your patience and understanding.	$119.90
N463180-5mg	5mg	Available within 8-12 weeks(?) Production requires sourcing of materials. We appreciate your patience and understanding.	$939.90

View related series

Anti-infection Fungal-Antibiotic

Basic Description

Synonyms	β-D-Allofuranuronic acid 5-[[(2S,3S,4S)-2-amino-4-hydroxy-4-(5-hydroxy-2-pyridinyl)-3-methyl1-oxobutyl]amino]-1,5-dideoxy-1-(3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-
Specifications & Purity	≥90%(HPLC)
Biochemical and Physiological Mechanisms	Nikkomycin Z, a nucleoside-peptide, is a selective competitive chitin synthesis inhibitor. Nikkomycin Z has antifungal effects and acts as a competitive analogue of the chitin synthase substrate UDP-N-acetylglucosamine.
Storage Temp	Store at 2-8°C
Shipped In	Wet ice
Product Description	Description Chemical structure: peptidyl nucleosideNikkomycin Z is used as a selective competitive inhibitor of chitin synthetase 3 in studies on fungal cell wall development. It is a potential treatment for humanEncephalitozoon hellem, a microsporidian species and is used to study the changes of chitin and β--glucan under Nikkomycin Z exposure.

Associated Targets(Human)

Homo sapiens (32628 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

CHS1 Chitin synthase 1 (112 Activities)

Discover Target: CHS1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Saccharomyces cerevisiae (19171 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Pichia kudriavzevii (7448 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Aspergillus fumigatus (16427 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Cryptococcus neoformans (21258 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Candida albicans (78123 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Nakaseomyces glabratus (9108 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Candida parapsilosis (8521 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Candida tropicalis (8381 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Fusarium oxysporum (3998 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mucor mucedo (338 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Benjaminiella poitrasii (79 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Cutaneotrichosporon cutaneum (20 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Coccidioides immitis (15 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Names and Identifiers

IUPAC Name	(2S)-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	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
InChi Key	WWJFFVUVFNBJTN-VHDFTHOZSA-N
Canonical SMILES	CC(C(C1=NC=C(C=C1)O)O)C(C(=O)NC(C2C(C(C(O2)N3C=CC(=O)NC3=O)O)O)C(=O)O)N
Isomeric SMILES	C[C@H]([C@@H](C1=NC=C(C=C1)O)O)[C@@H](C(=O)N[C@@H]([C@@H]2[C@H]([C@H]([C@@H](O2)N3C=CC(=O)NC3=O)O)O)C(=O)O)N
PubChem CID	456557
Molecular Weight	495.44

Certificates

Certificate of Analysis(COA)

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4 results found

Lot Number	Certificate Type	Date	Item
F2428275	Certificate of Analysis	Jun 18, 2024	N463180
F2428276	Certificate of Analysis	Jun 18, 2024	N463180
F2428277	Certificate of Analysis	Jun 18, 2024	N463180
F2428278	Certificate of Analysis	Jun 18, 2024	N463180

Chemical and Physical Properties

Solubility	H2O: soluble 5mg/mL

Safety and Hazards(GHS)

Pictogram(s)	GHS07
Signal	Warning
Hazard Statements	H315:Causes skin irritation H319:Causes serious eye irritation H335:May cause respiratory irritation
Precautionary Statements	P261:Avoid breathing dust/fume/gas/mist/vapors/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do - continue rinsing. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of water. P321:Specific treatment (see ... on this label). P405:Store locked up. P501:Dispose of contents/container to ... P264:Wash hands [and …] thoroughly after handling. P271:Use only outdoors or in a well-ventilated area. P304+P340:IF INHALED: Remove person to fresh air and keep comfortable for breathing. P403+P233:Store in a well-ventilated place. Keep container tightly closed. P362+P364:Take off contaminated clothing and wash it before reuse. P264+P265:Wash hands [and …] thoroughly after handling. Do not touch eyes. P337+P317:If eye irritation persists: Get medical help. P332+P317:If skin irritation occurs: Get medical help. P319:Get medical help if you feel unwell.
RIDADR	NONH for all modes of transport

References

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2. U Roos,S Mattern,H Schrempf,C Bormann. (1992-10-01) Histidine aminotransferase activity in Streptomyces tendae and its correlation with nikkomycin production.. FEMS microbiology letters, 76 ((1-2)): (185-190). [PMID:1427000]
3. H Decker,H Zähner,H Heitsch,W A König,H P Fiedler. (1991-08-01) Structure-activity relationships of the nikkomycins.. Journal of general microbiology, 137 ((8)): (1805-1813). [PMID:1955867]
4. L Popolo,D Gilardelli,P Bonfante,M Vai. (1997-01-01) Increase in chitin as an essential response to defects in assembly of cell wall polymers in the ggp1delta mutant of Saccharomyces cerevisiae.. Journal of bacteriology, 179 ((2)): (463-469). [PMID:8990299]
5. E Bigliardi,A M Bernuzzi,S Corona,S Gatti,M Scaglia,L Sacchi. (2000-10-19) In vitro efficacy of nikkomycin Z against the human isolate of the microsporidian species Encephalitozoon hellem.. Antimicrobial agents and chemotherapy, 44 ((11)): (3012-3016). [PMID:11036015]
6. Guojian Liao,Jine Li,Lei Li,Haihua Yang,Yuqing Tian,Huarong Tan. (2009-11-26) Selectively improving nikkomycin Z production by blocking the imidazolone biosynthetic pathway of nikkomycin X and uracil feeding in Streptomyces ansochromogenes.. Microbial cell factories, 8 (61-61). [PMID:19930628]
7. Xihong He,Rui Li,Yuanyuan Pan,Gang Liu,Huarong Tan. (2009-12-05) SanG, a transcriptional activator, controls nikkomycin biosynthesis through binding to the sanN-sanO intergenic region in Streptomyces ansochromogenes.. Microbiology (Reading, England), 156 ((Pt 3)): (828-837). [PMID:19959580]
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10. Christina S Stauffer,Annette W Fothergill,Michael G Rinaldi,Apurba Dutta. (2009-05-01) Studies on peptidyl nucleoside antibiotics: synthesis and antifungal evaluation of pyranosyl nucleoside analogs of nikkomycin.. Future medicinal chemistry, 1 ((2)): (379-389). [PMID:21425974]
11. Alexandra Binter,Gustav Oberdorfer,Sebastian Hofzumahaus,Stefanie Nerstheimer,Georg Altenbacher,Karl Gruber,Peter Macheroux. (2011-09-03) Characterization of the PLP-dependent aminotransferase NikK from Streptomyces tendae and its putative role in nikkomycin biosynthesis.. The FEBS journal, 278 ((21)): (4122-4135). [PMID:21884568]
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13. Judit Szilágyi,Richárd Földi,Sedigh Bayegan,Gábor Kardos,László Majoros. (2012-05-02) Effect of nikkomycin Z and 50% human serum on the killing activity of high-concentration caspofungin against Candida species using time-kill methodology.. Journal of chemotherapy (Florence, Italy), 24 ((1)): (18-25). [PMID:22546720]
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18. Emma Camacho,Christine Chrissian,Radames J B Cordero,Livia Liporagi-Lopes,Ruth E Stark,Arturo Casadevall. (2017-10-19) N-acetylglucosamine affects Cryptococcus neoformans cell-wall composition and melanin architecture.. Microbiology (Reading, England), 163 ((11)): (1540-1556). [PMID:29043954]
19. Hoda Moravej,Zahra Moravej,Maryam Yazdanparast,Mohammad Heiat,Ali Mirhosseini,Mehrdad Moosazadeh Moghaddam,Reza Mirnejad. (2018-06-30) Antimicrobial Peptides: Features, Action, and Their Resistance Mechanisms in Bacteria.. Microbial drug resistance (Larchmont, N.Y.), 24 ((6)): (747-767). [PMID:29957118]
20. Hui Hong,Markiyan Samborskyy,Yongjun Zhou,Peter F Leadlay. (2019-02-05) C-Nucleoside Formation in the Biosynthesis of the Antifungal Malayamycin A.. Cell chemical biology, 26 ((4)): (493-501). [PMID:30713097]
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23. Dekun Kong,Xia Wang,Ju Nie,Guoqing Niu. (2020-01-11) Regulation of Antibiotic Production by Signaling Molecules in Streptomyces.. Frontiers in microbiology, 10 (2927-2927). [PMID:31921086]
24. Bilin Dong,Wei Liu,Ruoyu Li,Yao Chen,Zhongsheng Tong,Xu Zhang,Liuqing Chen,Dongsheng Li. (2020-06-12) Muriform Cells Can Reproduce by Dividing in an Athymic Murine Model of Chromoblastomycosis due to Fonsecaea pedrosoi.. The American journal of tropical medicine and hygiene, 103 ((2)): (704-712). [PMID:32524944]
25. Lingjun Yu,Fengyu Du,Xusheng Chen,Yongbiao Zheng,Martha Morton,Fengquan Liu,Liangcheng Du. (2020-07-02) Identification of the Biosynthetic Gene Cluster for the anti-MRSA Lysocins through Gene Cluster Activation Using Strong Promoters of Housekeeping Genes and Production of New Analogs in Lysobacter sp. 3655.. ACS synthetic biology, 9 ((8)): (1989-1997). [PMID:32610008]
26. Phaneeswara-Rao Kommoju,Robert C Bruckner,Patricia Ferreira,Marilyn Schuman Jorns. (2009-06-18) Probing the role of active site residues in NikD, an unusual amino acid oxidase that catalyzes an aromatization reaction important in nikkomycin biosynthesis.. Biochemistry, 48 ((29)): (6951-6962). [PMID:19530706]
27. Guojian Liao,Jine Li,Lei Li,Haihua Yang,Yuqing Tian,Huarong Tan. (2010-01-26) Cloning, reassembling and integration of the entire nikkomycin biosynthetic gene cluster into Streptomyces ansochromogenes lead to an improved nikkomycin production.. Microbial cell factories, 9 (6-6). [PMID:20096125]
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38. Yuanyuan Pan,Linqi Wang,Xihong He,Yuqing Tian,Gang Liu,Huarong Tan. (2011-07-21) SabR enhances nikkomycin production via regulating the transcriptional level of sanG, a pathway-specific regulatory gene in Streptomyces ansochromogenes.. BMC microbiology, 11 (164-164). [PMID:21771341]
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