59456-70-1 Usage
Description
Nikkomycin Z is a nucleoside-type antibiotic derived from the culture filtrates of Streptomyces tendae. It is a uridine-based nucleoside-peptide antibiotic that inhibits fungal chitin biosynthesis by acting as a competitive chitin synthase inhibitor. Some analogs of Nikkomycin Z have been prepared through mutasynthesis, utilizing a uracil auxotroph of S. tendae.
Uses
Used in Pharmaceutical Industry:
Nikkomycin Z is used as an orally active antifungal therapeutic agent for the treatment of coccidioidomycosis, a fungal infection caused by Coccidioides species. It is effective in mouse models for coccidioidomycosis, demonstrating its potential as a treatment option for this disease.
However, it is important to note that Nikkomycin Z is too susceptible to photodegradation by sunlight, which limits its use in field applications and has prevented its commercial development for agricultural purposes. Despite this limitation, its potential as an antifungal agent in the pharmaceutical industry remains significant, particularly for the treatment of coccidioidomycosis.
Additionally, Nikkomycins, including Nikkomycin Z, have shown inhibitory effects on the growth of various plant pathogenic fungi, making them potentially useful in the agricultural industry for controlling fungal infections in crops. However, their inactivity against bacteria and yeasts limits their overall applicability in this field.
Pharmacology
By inhibiting chitin synthetase in fungi, nikkomycins
inhibit cell wall synthesis, ultimately causing fungal cells
to swell and burst.
Metabolism
There are no detailed reports on metabolism/transformation
of nikkomycins in the environment.
Check Digit Verification of cas no
The CAS Registry Mumber 59456-70-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,9,4,5 and 6 respectively; the second part has 2 digits, 7 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 59456-70:
(7*5)+(6*9)+(5*4)+(4*5)+(3*6)+(2*7)+(1*0)=161
161 % 10 = 1
So 59456-70-1 is a valid CAS Registry Number.
InChI:InChI=1/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
59456-70-1Relevant articles and documents
A synthesis of nikkomycin Z: Improved synthesis and protection of the pyridyl γ-hydroxy-α-aminobutanoic acid component
Saksena,Lovey,Girijavallabhan,Guzik,Ganguly
, p. 3267 - 3270 (2007/10/02)
The first synthesis of nikkomycin Z is described. An improvement of the isoxazoline-based methodology and an effective method for protection of 1b were devised. The application of oxalyditriazole (23) for peptide coupling proved most effective in completing the synthesis. A new and efficient synthesis of the prerequisite pyridyl E-olefin (5) is also described.
