Synonym
Hikizimycin; Anthelmycin; L 33876
IUPAC/Chemical Name
4-amino-1-[5-amino-6-[1-[4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,5,6-pentahydroxyhexyl]-3,4-dihydroxyoxan-2-yl]pyrimidin-2-one
InChi Key
VQQSDVBOXQHCHU-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H37N5O14/c22-7-1-2-26(21(37)25-7)19-16(36)12(32)9(24)17(39-19)18(15(35)14(34)10(30)5(29)3-27)40-20-13(33)8(23)11(31)6(4-28)38-20/h1-2,5-6,8-20,27-36H,3-4,23-24H2,(H2,22,25,37)
SMILES Code
O=C1N=C(N)C=CN1C2OC(C(OC3OC(CO)C(O)C(N)C3O)C(O)C(O)C(O)C(O)CO)C(N)C(O)C2O
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).
HS Tariff Code
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
583.55
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.
| 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: González A, Vázquez D, Jiménez A. Inhibition of translation in bacterial and eukaryotic systems by the antibiotic anthelmycin (hikizimycin). Biochim Biophys Acta. 1979 Feb 27;561(2):403-9. PubMed PMID: 371683.
2: Lacal JC, Vázquez D, Fernandez-Sousa JM, Carrasco L. Antibiotics that specifically block translation in virus-infected cells. J Antibiot (Tokyo). 1980 Apr;33(4):441-6. PubMed PMID: 6251018.
3: Rodriguez-Fonseca C, Amils R, Garrett RA. Fine structure of the peptidyl transferase centre on 23 S-like rRNAs deduced from chemical probing of antibiotic-ribosome complexes. J Mol Biol. 1995 Mar 24;247(2):224-35. PubMed PMID: 7707371.
4: Fürstner A, Wuchrer M. Concise approach to the "higher sugar" core of the nucleoside antibiotic hikizimycin. Chemistry. 2005 Dec 16;12(1):76-89. PubMed PMID: 16196060.
5: Vuilhorgne M, Ennifar S, Das BC, Paschal JW, Nagarajan R, Hagaman EW, Wenkert E. Structure analysis of the nucleoside disaccharide antibiotic anthelmycin by carbon-13 nuclear magnetic resonance spectroscopy. A structural revision of hikizimycin and its identity with anthelmycin. J Org Chem. 1977 Sep 30;42(20):3289-91. PubMed PMID: 903851.
6: Fernández-Puentes C. Permeability to inhibitors of protein synthesis in virus infected cells. Mol Biol Rep. 1984 Dec;10(2):65-8. PubMed PMID: 6527684.
7: Uchida K, Ichikawa T, Shimauchi Y, Ishikura T, Ozaki A. Hikizimycin, a new antibiotic. J Antibiot (Tokyo). 1971 Apr;24(4):259-62. PubMed PMID: 5572754.
8: Uchida K, Das BC. Hikosamine, a novel C11 aminosugar component of the antibiotic hikizimycin. Biochimie. 1973 May;55(5):635-6. PubMed PMID: 4754193.
9: Das BC, Defaye J, Uchida K. The structure of hikizimycin. I. Identification of 3-amino-3-deoxy-D-glucose and cytosine as structural components. Carbohydr Res. 1972 May;22(2):293-9. PubMed PMID: 5047747.
10: HAMMILL RL, HOEHN M. ANTHELMYCIN, A NEW ANTIBIOTIC WITH ANTHELMINTIC PROPERTIES. J Antibiot (Tokyo). 1964 May;17:100-3. PubMed PMID: 14171214.
11: Uchida K, Wolf H. Metabolic products of microorganisms 133. Inhibition of ribosomal peptidyl transferase by hikizimycin, a nucleoside antibiotic. J Antibiot (Tokyo). 1974 Oct;27(10):783-7. PubMed PMID: 4616934.
12: Masuda K, Nagatomo M, Inoue M. Direct assembly of multiply oxygenated carbon chains by decarbonylative radical-radical coupling reactions. Nat Chem. 2017 Mar;9(3):207-212. doi: 10.1038/nchem.2639. Epub 2016 Oct 31. PubMed PMID: 28221357.
