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MedKoo Cat#: 596323 | Name: Polyoxin C

Description:

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

Polyoxin C is a nucleoside antibiotic composed of heterocyclic moieties containing nitrogen.

Chemical Structure

Polyoxin C
Polyoxin C
CAS#21027-33-8

Theoretical Analysis

MedKoo Cat#: 596323

Name: Polyoxin C

CAS#: 21027-33-8

Chemical Formula: C11H15N3O8

Exact Mass: 317.0859

Molecular Weight: 317.25

Elemental Analysis: C, 41.65; H, 4.77; N, 13.25; O, 40.34

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 #
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Synonym
Polyoxin C; Julichrome Q(sub 1.3); Julimycin C;
IUPAC/Chemical Name
(S)-2-amino-2-((2R,3S,4R,5R)-3,4-dihydroxy-5-(5-(hydroxymethyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)acetic acid
InChi Key
TZQKKPBFBDTCRN-AJDRIWCOSA-N
InChi Code
InChI=1S/C11H15N3O8/c12-4(10(19)20)7-5(16)6(17)9(22-7)14-1-3(2-15)8(18)13-11(14)21/h1,4-7,9,15-17H,2,12H2,(H,19,20)(H,13,18,21)/t4-,5-,6+,7+,9+/m0/s1
SMILES Code
N[C@H](C(O)=O)[C@H]1O[C@@H](N2C=C(C(NC2=O)=O)CO)[C@@H]([C@@H]1O)O
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 317.25 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: Tamura O, Takeda K, Mita N, Sakamoto M, Okamoto I, Morita N, Ishibashi H. Stereoselective vinylogous Mannich reaction of 2-trimethylsilyloxyfuran with N-gulosyl nitrones. Org Biomol Chem. 2011 Nov 7;9(21):7411-9. doi: 10.1039/c1ob06067h. Epub 2011 Sep 7. PubMed PMID: 21897975. 2: Cesario C, Miller MJ. Syntheses of carbocyclic uracil polyoxin C analogs: application of Pd(0)/InI-allylation of 4-acetoxy-2-azetidinone. J Org Chem. 2009 Aug 7;74(15):5730-3. doi: 10.1021/jo900861x. PubMed PMID: 19514728; PubMed Central PMCID: PMC2745051. 3: Plant A, Thompson P, Williams DM. Application of the Ugi reaction for the one-pot synthesis of uracil polyoxin C analogues. J Org Chem. 2009 Jul 3;74(13):4870-3. doi: 10.1021/jo900244m. PubMed PMID: 19456169. 4: Plant A, Thompson P, Williams DM. Stereoselective synthesis of novel uracil polyoxin C conjugates as substrate analogues of chitin synthase. J Org Chem. 2008 May 16;73(10):3714-24. doi: 10.1021/jo702564y. Epub 2008 Apr 24. PubMed PMID: 18433174. 5: Li F, Brogan JB, Gage JL, Zhang D, Miller MJ. Chemoenzymatic synthesis and synthetic application of enantiopure aminocyclopentenols: total synthesis of carbocyclic (+)-uracil polyoxin C and its alpha-epimer. J Org Chem. 2004 Jun 25;69(13):4538-40. PubMed PMID: 15202916. 6: Mita N, Tamura O, Ishibashi H, Sakamoto M. Nucleophilic addition reaction of 2-trimethylsilyloxyfuran to N-gulosyl-C-alkoxymethylnitrones: synthetic approach to polyoxin C. Org Lett. 2002 Apr 4;4(7):1111-4. PubMed PMID: 11922795. 7: Ghosh AK, Wang Y. Total Synthesis of (+)-Polyoxin J. J Org Chem. 1999 Apr 16;64(8):2789-2795. PubMed PMID: 11674347. 8: Zhang D, Miller MJ. Total Synthesis of (+/-) Carbocyclic Polyoxin C and Its alpha-Epimer. J Org Chem. 1998 Feb 6;63(3):755-759. PubMed PMID: 11672070. 9: Merino P, Franco S, Merchan FL, Tejero T. Stereodivergent approaches to the synthesis of isoxazolidine analogues of alpha-amino acid nucleosides. Total synthesis of isoxazolidinyl deoxypolyoxin C and uracil polyoxin C. J Org Chem. 2000 Sep 8;65(18):5575-89. PubMed PMID: 10970296. 10: Tamura O, Gotanda K, Yoshino J, Morita Y, Terashima R, Kikuchi M, Miyawaki T, Mita N, Yamashita M, Ishibashi H, Sakamoto M. Design, synthesis, and 1,3-dipolar cycloaddition of (5R)- [and (5S)]-5,6-dihydro-5-phenyl-2H-1,4-oxazin-2-one N-oxides as chiral (E)-geometry-fixed alpha-alkoxycarbonylnitrones. J Org Chem. 2000 Dec 15;65(25):8544-51. PubMed PMID: 11112574. 11: Khare RK, Becker JM, Naider FR. Synthesis and anticandidal properties of polyoxin L analogues containing alpha-amino fatty acids. J Med Chem. 1988 Mar;31(3):650-6. PubMed PMID: 3279209. 12: Shenbagamurthi P, Smith HA, Becker JM, Naider F. Synthesis and biological properties of chitin synthetase inhibitors resistant to cellular peptidases. J Med Chem. 1986 May;29(5):802-9. PubMed PMID: 2939243. 13: Smith HA, Shenbagamurthi P, Naider F, Kundu B, Becker JM. Hydrophobic polyoxins are resistant to intracellular degradation in Candida albicans. Antimicrob Agents Chemother. 1986 Jan;29(1):33-9. PubMed PMID: 3524423; PubMed Central PMCID: PMC180359. 14: Emmer G, Ryder NS, Grassberger MA. Synthesis of new polyoxin derivatives and their activity against chitin synthase from Candida albicans. J Med Chem. 1985 Mar;28(3):278-81. PubMed PMID: 3156247. 15: Naider F, Shenbagamurthi P, Steinfeld AS, Smith HA, Boney C, Becker JM. Synthesis and biological activity of tripeptidyl polyoxins as antifungal agents. Antimicrob Agents Chemother. 1983 Nov;24(5):787-96. PubMed PMID: 6362556; PubMed Central PMCID: PMC185943. 16: Shenbagamurthi P, Smith HA, Becker JM, Steinfeld A, Naider F. Design of anticandidal agents: synthesis and biological properties of analogues of polyoxin L. J Med Chem. 1983 Oct;26(10):1518-22. PubMed PMID: 6352943. 17: Isono K, Suzuki S. The strucutre of polyoxin C. Tetrahedron Lett. 1968 Jan;2:203-8. PubMed PMID: 5636922.

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