Tetrahydroechinocandin B
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| Category | Antifungal |
| Catalog number | BBF-05891 |
| CAS | 54651-06-8 |
| Molecular Weight | 1064.27 |
| Molecular Formula | C52H85N7O16 |
| Purity | 95% by HPLC |
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Description
Tetrahydroechinocandin B, a cyclic hexapeptide containing a fatty acyl side chain, inhibits 1,3-beta-D-glucan synthesis. It is an intermediate of anidulafungin.
Specification
| Synonyms | Echinocandin B, 1-[(4R,5R)-4,5-dihydroxy-N2-(1-oxooctadecyl)-L-ornithine]-; Echinocandin B, tetrahydro-; L 687,901; Octadecanimidic acid, N-[(2R,6S,7E,9S,11R,12R,14aS,15S,16S,20S,23R,24E,25aS)-23-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-2,3,5,6,9,10,11,12,14a,15,16,17,19,20,23,25a-hexadecahydro-2,8,11,12,14,15,22,25-octahydroxy-6,20-bis[(1R)-1-hydroxyethyl]-16-methyl-5,19-dioxo-1H-dipyrrolo[2,1-c:2',1'-l][1,4,7,10,13,16]hexaazacycloheneicosin-9-yl]-; L-687901 |
| Storage | Store at -20°C |
| IUPAC Name | N-{(2R,6S,7E,9S,11R,12R,14aS,15S,16S,20S,23R,24E,25aS)-23-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-2,8,11,12,14,15,22,25-octahydroxy-6,20-bis[(1R)-1-hydroxyethyl]-16-methyl-5,19-dioxo-2,3,5,6,9,10,11,12,14a,15,16,17,19,20,23,25a-hexadecahydro-1H-dipyrrolo[2,1-c:2',1'-l][1,4,7,10,13,16]hexaazacyclohenicosin-9-yl}octadecanimidic acid |
| Canonical SMILES | CCCCCCCCCCCCCCCCCC(=O)NC1CC(C(NC(=O)C2C(C(CN2C(=O)C(NC(=O)C(NC(=O)C3CC(CN3C(=O)C(NC1=O)C(C)O)O)C(C(C4=CC=C(C=C4)O)O)O)C(C)O)C)O)O)O |
| InChI | InChI=1S/C52H85N7O16/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-38(65)53-35-26-37(64)48(71)57-50(73)42-43(66)29(2)27-59(42)52(75)40(31(4)61)55-49(72)41(45(68)44(67)32-21-23-33(62)24-22-32)56-47(70)36-25-34(63)28-58(36)51(74)39(30(3)60)54-46(35)69/h21-24,29-31,34-37,39-45,48,60-64,66-68,71H,5-20,25-28H2,1-4H3,(H,53,65)(H,54,69)(H,55,72)(H,56,70)(H,57,73)/t29-,30+,31+,34+,35-,36-,37+,39-,40-,41+,42-,43-,44-,45-,48+/m0/s1 |
| InChI Key | CSFSSKWGOYOSPM-SFNHZBHUSA-N |
Properties
| Appearance | Crystal |
| Boiling Point | 1278.0±75.0°C at 760 mmHg |
| Melting Point | 210-212°C (dec.) |
| Density | 1.4±0.1 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol |
Reference Reading
1. Effect of branch frequency in Aspergillus oryzae on protein secretion and culture viscosity
S P Bocking, M G Wiebe, G D Robson, K Hansen, L H Christiansen, A P Trinci Biotechnol Bioeng. 1999 Dec 20;65(6):638-48. doi: 10.1002/(sici)1097-0290(19991220)65:63.0.co;2-k.
Highly branched mutants of two strains of Aspergillus oryzae (IFO4177, which produces alpha-amylase, and a transformant of IFO4177 [AMG#13], which produces heterologous glucoamylase in addition to alpha-amylase) were generated by UV or nitrous acid mutagenesis. Four mutants of the parental strain (IFO4177), which were 10 to 50% more branched than the parental strain, were studied in stirred batch culture and no differences were observed in either the amount or the rate of enzyme production. Five mutants of the transformed parental strain (AMG#13), which were 20 to 58% more branched than the parental strain, were studied in either batch, fed-batch or continuous culture. In batch culture, three of the mutants produced more glucoamylase than the transformed parental strain, although only two mutants produced more glucoamylase and alpha-amylase combined. No increase in enzyme production was observed in either chemostat or fed-batch culture. Cultures of highly branched mutants were less viscous than those of the parental and transformed parental strains. A linear relationship was found between the degree of branching (measured as hyphal growth unit length) and culture viscosity (measured as the torque exerted on the rheometer impeller) for these strains. DOT-controlled fed-batch cultures (in which the medium feed rate was determined by the DOT) were thus inoculated with either the transformed parent or highly branched mutants of the transformed parent to determine whether the reduced viscosity would improve aeration and give higher enzyme yields. The average rate of medium addition was higher for the two highly branched mutants (ca. 8.3 g medium h(-1)) than for the parental strain (5.7 g medium h(-1)). Specific enzyme production in the DOT controlled fed-batch cultures was similar for all three strains (approx. 0.24 g alpha-amylase and glucoamylase [g of biomass](-1)), but one of the highly branched mutants made more total enzyme (24.3 +/- 0.2 g alpha-amylase and glucoamylase) than the parental strain (21.7 +/- 0.4 g alpha-amylase and glucoamylase).
2. In vitro antifungal activities and in vivo efficacies of 1,3-beta-D-glucan synthesis inhibitors L-671,329, L-646,991, tetrahydroechinocandin B, and L-687,781, a papulacandin
K Bartizal, G Abruzzo, C Trainor, D Krupa, K Nollstadt, D Schmatz, R Schwartz, M Hammond, J Balkovec, F Vanmiddlesworth Antimicrob Agents Chemother. 1992 Aug;36(8):1648-57. doi: 10.1128/AAC.36.8.1648.
The in vivo anti-Candida activities of 1,3-beta-D-glucan synthesis inhibitors L-671,329, L-646,991 (cilofungin), L-687,901 (tetrahydroechinocandin B), and L-687,781 (a papulacandin analog) were evaluated by utilizing a murine model of disseminated candidiasis that has enhanced susceptibility to Candida albicans but increased sensitivity for discriminating antifungal efficacy. DBA/2 mice were challenged intravenously with 1 x 10(4) to 5 x 10(4) CFU of C. albicans MY1055 per mouse. Compounds were administered intraperitoneally at concentrations ranging from 1.25 to 10 mg/kg of body weight twice daily for 4 days. At 6 h and 1, 2, 3, 4, 7, and 9 days after challenge, five mice per group were sacrificed and their kidneys were homogenized and plated for enumeration of Candida organisms (CFU per gram). Progressiveness of response trends and no-statistical-significance-of-trend doses were derived to rank compound efficacy. 1,3-beta-D-Glucan synthesis 50% inhibitory concentrations were determined by using a C. albicans (MY1208) membrane glucan assay. Candida and Cryptococcus neoformans MICs and minimal fungicidal concentrations were determined by broth microdilution. L-671,329, L-646,991, L-687,901, and L-687,781 showed similar 1,3-beta-D-glucan activities, with 50% inhibitory concentrations of 0.64, 1.30, 0.85, and 0.16 micrograms/ml, respectively. Data from in vitro antifungal susceptibility studies showed that L-671,329, L-646,991, and L-687,901 had similar MICs ranging from 0.5 to 1.0 micrograms/ml, while L-687,781 showed slightly higher MICs of 1.0 to 2.0 micrograms/ml for C. albicans MY1055. Lipopeptide compounds were ineffective against C. neoformans strains. Results from in vivo experiments comparing significant trend and progressiveness in response analyses indicated that L-671,329 and L-646,991 were equipotent but slightly less active than L-687-901, while L-687,781 was ineffective at 10 mg/kg. Fungicidal activities of L-671,329, L-646,991, and L-687,901 were observed in vivo, with significant reduction in Candida CFU per gram of kidneys compared with those in sham-treated mice at doses of > or = 2.5 mg/kg evident as early as 1 day after challenge.
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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
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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
