Nikkomycin Z from Streptomyces tendae

Base Information

• Chemical Name: Nikkomycin Z from Streptomyces tendae
• CAS No.: 59456-70-1
• Molecular Formula: C20H25N5O10
• Molecular Weight: 495.446
• European Community (EC) Number: 637-378-7
• Wikidata: Q105314064
• Mol file: 59456-70-1.mol

Synonyms:neopolyoxin C;nikkomycin;nikkomycin Z

Chemical Property of Nikkomycin Z from Streptomyces tendae

Chemical Property:

• Refractive Index: 1.678
• PKA: 2.70±0.10(Predicted)
• PSA: 250.32000
• Density: 1.646 g/cm³
• LogP: -2.38600
• Storage Temp.: 2-8°C
• Solubility.: H2O: soluble5mg/mL
• XLogP3: -5.6
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 8
• Exact Mass: 495.16014201
• Heavy Atom Count: 35
• Complexity: 871

Purity/Quality:

98% ^*data from raw suppliers

Nikkomycin Z from Streptomyces tendae ≥90% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• 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
• Description: Nucleoside-type antibiotic isolated from culture filtrates of Streptomyces tendae (19). Some analogs were also prepared by mutasynthesis, utilizing a uracil auxotroph of S. tendae.
• Uses: Nikkomycins inhibit the growth of various plant pathogenic fungi but are inactive against bacteria and yeasts. Too susceptible to photodegradation by sunlight to be used in field application, and thus not developed commercially for agricultural use. Among the nikkomycins, nikkomycin Z is an orally active antifungal therapeutic agent for coccidioidomycosis. It is a competitive chitin synthase inhibitor that has been evaluated in mouse models for coccidioidomycosis.

Technology Process of Nikkomycin Z from Streptomyces tendae

There total 5 articles about Nikkomycin Z from Streptomyces tendae which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(S)-[(2S,3S,4S)-2-Benzyloxycarbonylamino-4-(5-benzyloxy-pyridin-2-yl)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyrylamino]-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-acetic acid → nikkomycin Z (59456-70-1)

Guidance literature:

With methanol; formic acid; water; palladium; at 20 ℃; for 2h;

DOI:10.1016/S0040-4039(00)73678-1

Reference yield:

C35H62N2O4Si3 → nikkomycin Z (59456-70-1)

Guidance literature:

Multi-step reaction with 4 steps

1: Ambient temperature

2: MeOH, H₂O, K₂CO₃ / tetrahydrofuran / 0.5 h / Ambient temperature

3: 1.) oxalylditriazole, 2.) N-methylmorpholine / 1.) CH₃CN, 20 deg C, 3 h, 2.) DMSO, 20 deg C, 48 h

4: HCOOH, MeOH, H₂O / Pd / 2 h / 20 °C

With 4-methyl-morpholine; methanol; formic acid; oxalylditriazole; water; potassium carbonate; palladium; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)73678-1

Reference yield:

C37H54N2O6Si2 → nikkomycin Z (59456-70-1)

Guidance literature:

Multi-step reaction with 3 steps

1: MeOH, H₂O, K₂CO₃ / tetrahydrofuran / 0.5 h / Ambient temperature

2: 1.) oxalylditriazole, 2.) N-methylmorpholine / 1.) CH₃CN, 20 deg C, 3 h, 2.) DMSO, 20 deg C, 48 h

3: HCOOH, MeOH, H₂O / Pd / 2 h / 20 °C

With 4-methyl-morpholine; methanol; formic acid; oxalylditriazole; water; potassium carbonate; palladium; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)73678-1

Downstream raw materials:

2-amino-4-hydroxy-4-(5-hydroxy-2-pyridyl)-3-methylbutyric acid

1-(5'-amino-5'-deoxy-α-D-allofuranuronosyl)uracil

2-amino-4-hydroxy-4-(5-hydroxy-2-pyridyl)-3-methylbutyric acid

Refernces

• 1、 -. "Antibiotics, a process for their preparation and their use as plant protection agents". . . Retrieved 2008/06/13.