Saccharocarcin B
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| Category | Antibiotics |
| Catalog number | BBF-02641 |
| CAS | 158475-33-3 |
| Molecular Weight | 1254.54 |
| Molecular Formula | C68H103NO20 |
| Purity | >99% by HPLC |
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Description
An unusual tetronic acid structurally related to kijanimicin, chlorothricin, tetrocarcin and versipelostatin; has pronounced activity against gram positive bacteria and chlamydia trachomatis; inhibits transcription from the promoter of GRP78; appears to target the phosphatidylinositide-3-kinase/akt signalling pathway.
Specification
| Synonyms | 10-[[4-(acetylamino)-2,4,6-trideoxy-3-C-methylhexopyranosyl]oxy]-4-[[O-2,6-dideoxyhexopyranosyl-(1→4)-O-2,6-dideoxy-3-O-(tetrahydro-5-hydroxy-6-methyl-2H-pyran-2-yl)hexopyranosyl-(1→4)-2,6-dideoxyhexopyranosyl]oxy]-2,3,4,4a,6a,9,10,12a,15,16,20a,20b-dodecahydro-21-hydroxy-1,3,7,9,11,20a-hexamethyl-15-propyl-18H-16a,19-metheno-16aH-benzo[b]naphth[2,1-j]oxacyclotetradecin-18,20(1H)-dione |
| Storage | Store at -20°C |
| IUPAC Name | N-[(2S,3S,4S,6R)-6-[[(1S,3R,6S,7E,9S,11E,13S,16S,17S,18S,20S,21R,22S,23E)-17-[(2S,4R,5R,6R)-5-[(2R,4R,5S,6R)-5-[(2R,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4-[(2S,5R,6S)-5-hydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-23-hydroxy-8,10,12,18,20,22-hexamethyl-25,27-dioxo-3-propyl-26-oxapentacyclo[22.2.1.01,6.013,22.016,21]heptacosa-4,7,11,14,23-pentaen-9-yl]oxy]-4-hydroxy-2,4-dimethyloxan-3-yl]acetamide |
| Canonical SMILES | CCCC1CC23C(C=C1)C=C(C(C(C=C(C4C=CC5C(C4(C(=C(C2=O)C(=O)O3)O)C)C(CC(C5OC6CC(C(C(O6)C)OC7CC(C(C(O7)C)OC8CC(C(C(O8)C)O)O)O)OC9CCC(C(O9)C)O)C)C)C)C)OC1CC(C(C(O1)C)NC(=O)C)(C)O)C |
| InChI | InChI=1S/C68H103NO20/c1-15-16-42-17-18-43-25-35(6)58(88-54-30-66(13,78)62(40(11)83-54)69-41(12)70)33(4)23-31(2)45-20-19-44-56(67(45,14)63(75)55-64(76)68(43,29-42)89-65(55)77)32(3)24-34(5)59(44)85-53-28-49(84-50-22-21-46(71)36(7)79-50)61(39(10)82-53)87-52-27-48(73)60(38(9)81-52)86-51-26-47(72)57(74)37(8)80-51/h17-20,23,25,32-34,36-40,42-54,56-62,71-75,78H,15-16,21-22,24,26-30H2,1-14H3,(H,69,70)/b31-23+,35-25+,63-55+/t32-,33?,34-,36-,37+,38+,39+,40-,42-,43-,44-,45-,46+,47+,48+,49+,50-,51+,52+,53+,54-,56+,57+,58-,59-,60+,61+,62-,66-,67+,68-/m0/s1 |
| InChI Key | WVWPUYZPOCJSRH-APOLWHJQSA-N |
| Source | Amycolatopsis sp. |
Properties
| Appearance | White Solid |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | 210°C |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Limited water solubility. |
Reference Reading
1. Hepatitis B Vaccines
Greet Hendrickx, Pierre Van Damme, Alex Vorsters, Jade Pattyn J Infect Dis . 2021 Sep 30;224(12 Suppl 2):S343-S351. doi: 10.1093/infdis/jiaa668.
Hepatitis B is caused by the hepatitis B virus (HBV), which infects the liver and may lead to chronic liver disease, including cirrhosis and hepatocellular carcinoma. HBV represents a worldwide public health problem, causing major morbidity and mortality. Affordable, safe, and effective, hepatitis B vaccines are the best tools we have to control and prevent hepatitis B. In 2019, coverage of 3 doses of the hepatitis B vaccine reached 85% worldwide compared to around 30% in 2000. The effective implementation of hepatitis B vaccination programs has resulted in a substantial decrease in the HBV carrier rate and hepatitis B-related morbidity and mortality. This article summarizes the great triumphs of the hepatitis B vaccine, the first anticancer and virus-like-particle-based vaccine. In addition, existing unresolved issues and future perspectives on hepatitis B vaccination required for global prevention of HBV infection are discussed.
2. Hepatitis B today
Nikolaos J Lygidakis, Christine Manti, Michael Safioleas Hepatogastroenterology . 2007 Mar;54(74):545-8.
Hepatitis B remains a major problem for public health worldwide and represents a challenging disease for practicing physicians. Of the 2 billion people who have been infected with the hepatitis B virus, more than 350 million have chronic infections. These chronically infected individuals are at high risk of death from cirrhosis and liver cancer. The use of new antiviral drugs, such us nucleotides analogues, offer good hope in the prognosis of patients suffering from chronic hepatitis B.
3. Quantitative Assessment of B-B-B, B-Hb -B, and B-Ht Bonds: From BH3 to B12 H122
Elfi Kraka, Hans Hagemann, Latévi Max Lawson Daku, Daniel Sethio Chemphyschem . 2019 Aug 5;20(15):1967-1977. doi: 10.1002/cphc.201900364.
We report the thermodynamic stabilities and the intrinsic strengths of three-center-two-electron B-B-B and B-Hb-B bonds (Hb: bridging hydrogen), and two-center-two-electron B-Htbonds (Ht: terminal hydrogen) which can be served as a new, effective tool to determine the decisive role of the intermediates of hydrogenation/dehydrogenation reactions of borohydride. The calculated heats of formation were obtained with the G4 composite method and the intrinsic strengths of B-B-B, B-Hb-B, and B-Htbonds were derived from local stretching force constants obtained at the B3LYP-D2/cc-pVTZ level of theory for 21 boron-hydrogen compounds, including 19 intermediates. The Quantum Theory of Atoms in Molecules (QTAIM) was used to deepen the inside into the nature of B-B-B, B-Hb-B, and B-Htbonds. We found that all of the experimentally identified intermediates hindering the reversibility of the decomposition reactions are thermodynamically stable and possess strong B-B-B, B-Hb-B, and B-Htbonds. This proves that thermodynamic data and intrinsic B-B-B, B-Hb-B, and B-Htbond strengths form a new, effective tool to characterize new (potential) intermediates and to predict their role for the reversibility of the hydrogenation/dehydrogenation reactions.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
