Nulceocidin

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

MedKoo CAT#: 584874

CAS#: 24751-69-7

Description: Nulceocidin is an antibiotic and fluorine-containing nucleoside produced by Streptomyces calvus.


Price and Availability

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Nulceocidin is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 584874
Name: Nulceocidin
CAS#: 24751-69-7
Chemical Formula: C10H13FN6O6S
Exact Mass: 364.0601
Molecular Weight: 364.3084
Elemental Analysis: C, 32.97; H, 3.60; F, 5.21; N, 23.07; O, 26.35; S, 8.80


Synonym: Nulceocidin; Antibiotic T-3018; T-3018

IUPAC/Chemical Name: Adenosine, 4'-C-fluoro-, 5'-sulfamate

InChi Key: LTBCQBSAWAZBDF-MLTZYSBQSA-N

InChi Code: InChI=1S/C10H13FN6O6S/c11-10(1-22-24(13,20)21)6(19)5(18)9(23-10)17-3-16-4-7(12)14-2-15-8(4)17/h2-3,5-6,9,18-19H,1H2,(H2,12,14,15)(H2,13,20,21)/t5-,6+,9-,10-/m1/s1

SMILES Code: O[C@@H]([C@H]([C@H](N1C=NC2=C(N=CN=C21)N)O3)O)[C@@]3(F)COS(=O)(N)=O


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:
>3 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:
2934990300


References

1: Zhu XM, Hackl S, Thaker MN, Kalan L, Weber C, Urgast DS, Krupp EM, Brewer A, Vanner S, Szawiola A, Yim G, Feldmann J, Bechthold A, Wright GD, Zechel DL. Biosynthesis of the Fluorinated Natural Product Nucleocidin in Streptomyces calvus Is Dependent on the bldA-Specified Leu-tRNA(UUA) Molecule. Chembiochem. 2015 Nov;16(17):2498-506. doi: 10.1002/cbic.201500402. Epub 2015 Oct 22. PubMed PMID: 26374477.

2: Feng X, Al Maharik N, Bartholomé A, Janso JE, Reilly U, O'Hagan D. Incorporation of [(2)H(1)]-(1R,2R)- and [(2)H(1)]-(1S,2R)-glycerols into the antibiotic nucleocidin in Streptomyces calvus. Org Biomol Chem. 2017 Oct 4;15(38):8006-8008. doi: 10.1039/c7ob02163a. PubMed PMID: 28920128.

3: Bartholomé A, Janso JE, Reilly U, O'Hagan D. Fluorometabolite biosynthesis: isotopically labelled glycerol incorporations into the antibiotic nucleocidin in Streptomyces calvus. Org Biomol Chem. 2016 Dec 20;15(1):61-64. PubMed PMID: 27845468.

4: Carvalho MF, Oliveira RS. Natural production of fluorinated compounds and biotechnological prospects of the fluorinase enzyme. Crit Rev Biotechnol. 2017 Nov;37(7):880-897. doi: 10.1080/07388551.2016.1267109. Epub 2017 Jan 3. Review. PubMed PMID: 28049355.

5: Morton GO, Lancaster JE, Van Lear GE, Fulmor W, Meyer WE. The structure of nucleocidin. 3. (A new structure). J Am Chem Soc. 1969 Mar 12;91(6):1535-7. PubMed PMID: 5776261.

6: Florini JR, Bird HH, Bell PH. Inhibition of protein synthesis in vitro and in vivo by nucleocidin, an antitrypanosomal antibiotic. J Biol Chem. 1966 Mar 10;241(5):1091-8. PubMed PMID: 5933868.

7: Williamson J, Macadam RF. Drug effects on the fine structure of Trypanosoma rhodesiense: puromycin and its aminonucleoside, Cordycepin and Nucleocidin. Trans R Soc Trop Med Hyg. 1976;70(2):130-7. PubMed PMID: 1085509.

8: BACKUS EJ, TRESNER HD, CAMPBELL TH. The nucleocidin and alazopetin producing organisms: two new species of Streptomyces. Antibiot Chemother (Northfield). 1957 Oct;7(10):532-41. PubMed PMID: 24544578.

9: THOMAS SO, SINGLETON VL, LOWERY JA, SHARPE RW, PRUESS LM, PORTER JN, MOWAT JH, BOHONOS N. Nucleocidin, a new antibiotic with activity against Trypanosomes. Antibiot Annu. 1956-1957:716-21. PubMed PMID: 13425454.

10: HEWITT RI, GUMBLE AR, TAYLOR LH, WALLACE WS. The activity of a new antibiotic, nucleocidin, in experimental infections with Trypanosoma equiperdum. Antibiot Annu. 1956-1957:722-9. PubMed PMID: 13425455.

11: Zhang S, Klementz D, Zhu J, Makitrynskyy R, Ola Pasternak AR, Günther S, Zechel DL, Bechthold A. Genome mining reveals the origin of a bald phenotype and a cryptic nucleocidin gene cluster in Streptomyces asterosporus DSM 41452. J Biotechnol. 2019 Feb 20;292:23-31. doi: 10.1016/j.jbiotec.2018.12.016. Epub 2019 Jan 11. PubMed PMID: 30641108.

12: Jenkins ID, Verheyden JP, Moffatt JG. Synthesis of the nucleoside antibiotic nucleocidin. J Am Chem Soc. 1971 Aug 25;93(17):4323-4. PubMed PMID: 5131149.

13: TOBIE EJ. The trypanocidal effect of nucleocidin in vivo. J Parasitol. 1957 Jun;43(3):291-3. PubMed PMID: 13439466.

14: STEPHEN LE, GRAY AR. The trypanocidal activity of nucleocidin against Trypanosoma vivax in West African zebu cattle. J Parasitol. 1960 Aug;46:509-14. PubMed PMID: 13834368.

15: Shuman D, Robbins RK, Robins MJ. The synthesis of adenine 5'-O-sulfamoyl nucleosides related to nucleocidin. J Am Chem Soc. 1969 Jun 4;91(12):3391-2. PubMed PMID: 5791926.

16: Shuman DA, Robins MJ, Robins RK. The synthesis of nucleos9de sulfamates related to nucleocidin. J Am Chem Soc. 1970 Jun 3;92(11):3434-40. PubMed PMID: 5422764.

17: Jaffe JJ, McCormack JJ, Meymerian E. Trypanocidal properties of 5'-O-Sulfamoyladenosine, a close structural analog of nucleocidin. Exp Parasitol. 1970 Dec;28(3):535-43. PubMed PMID: 5499671.

18: Jenkins ID, Verheyden JP, Moffatt JG. 4'-Substituted nucleosides. 2. Synthesis of the nucleoside antibiotic nucleocidin. J Am Chem Soc. 1976 May 26;98(11):3346-57. PubMed PMID: 1262649.

19: Kalan L, Gessner A, Thaker MN, Waglechner N, Zhu X, Szawiola A, Bechthold A, Wright GD, Zechel DL. A cryptic polyene biosynthetic gene cluster in Streptomyces calvus is expressed upon complementation with a functional bldA gene. Chem Biol. 2013 Oct 24;20(10):1214-24. doi: 10.1016/j.chembiol.2013.09.006. Epub 2013 Oct 10. PubMed PMID: 24120331.

20: Bacchi J, Lambros C, Goldberg B, Hutner SH, de Carvalho GD. Susceptibility of an insect Leptomonas and Crithidia fasciculata to several established antitrypanosomatid agents. Antimicrob Agents Chemother. 1974 Dec;6(6):785-90. PubMed PMID: 4451351; PubMed Central PMCID: PMC444737.