Respirantin
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| Category | Others |
| Catalog number | BBF-04959 |
| CAS | 149598-67-4 |
| Molecular Weight | 747.83 |
| Molecular Formula | C37H53N3O13 |
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Specification
| Synonyms | Cyclodepsipeptide 1 |
| IUPAC Name | N-[(2S,5S,8S,13S,16R,17S)-5-butan-2-yl-2,10,10,16-tetramethyl-8,13-bis(2-methylpropyl)-3,6,9,11,14,18-hexaoxo-1,4,12,15-tetraoxa-7-azacyclooctadec-17-yl]-3-formamido-2-hydroxybenzamide |
| Canonical SMILES | CCC(C)C1C(=O)NC(C(=O)C(C(=O)OC(C(=O)OC(C(C(=O)OC(C(=O)O1)C)NC(=O)C2=C(C(=CC=C2)NC=O)O)C)CC(C)C)(C)C)CC(C)C |
| InChI | InChI=1S/C37H53N3O13/c1-11-20(6)29-32(45)39-25(15-18(2)3)30(43)37(9,10)36(49)52-26(16-19(4)5)34(47)50-21(7)27(35(48)51-22(8)33(46)53-29)40-31(44)23-13-12-14-24(28(23)42)38-17-41/h12-14,17-22,25-27,29,42H,11,15-16H2,1-10H3,(H,38,41)(H,39,45)(H,40,44)/t20?,21-,22+,25+,26+,27+,29+/m1/s1 |
| InChI Key | HJNZTHHOZWMVPB-WCSXKIRISA-N |
Reference Reading
1. Rare Streptomyces N-formyl amino-salicylamides inhibit oncogenic K-Ras
Angela A Salim, Kwang-Jin Cho, Lingxiao Tan, Michelle Quezada, Ernest Lacey, John F Hancock, Robert J Capon Org Lett. 2014 Oct 3;16(19):5036-9. doi: 10.1021/ol502376e. Epub 2014 Sep 19.
During a search for inhibitors of oncogenic K-Ras, we detected two known and two new examples of the rare neoantimycin structure class from a liquid cultivation of Streptomyces orinoci, and reassigned/assigned structures to all based on detailed spectroscopic analysis and microscale C3 Marfey's and C3 Mosher chemical degradation/derivatization/analysis. SAR investigations inclusive of the biosynthetically related antimycins and respirantin, and synthetic benzoxazolone, documented a unique N-formyl amino-salicylamide pharmacophore as a potent inhibitor of oncogenic K-Ras.
2. Development, Characterization, and Standardization of a Nose-Only Inhalation Exposure System for Exposure of Rabbits to Small-Particle Aerosols Containing Francisella tularensis
Katherine J O'Malley, Jennifer D Bowling, Eileen M Barry, Karsten R O Hazlett, Douglas S Reed Infect Immun. 2019 Jul 23;87(8):e00198-19. doi: 10.1128/IAI.00198-19. Print 2019 Aug.
Inhalation of Francisella tularensis causes pneumonic tularemia in humans, a severe disease with a 30 to 60% mortality rate. The reproducible delivery of aerosolized virulent bacteria in relevant animal models is essential for evaluating medical countermeasures. Here we developed optimized protocols for infecting New Zealand White (NZW) rabbits with aerosols containing F. tularensis We evaluated the relative humidity, aerosol exposure technique, and bacterial culture conditions to optimize the spray factor (SF), a central metric of aerosolization. This optimization reduced both inter- and intraday variability and was applicable to multiple isolates of F. tularensis Further improvements in the accuracy and precision of the inhaled pathogen dose were achieved through enhanced correlation of the bacterial culture optical density and the number of CFU. Plethysmograph data collected during exposures found that respiratory function varied considerably between rabbits, was not a function of weight, and did not improve with acclimation to the system. Live vaccine strain (LVS)-vaccinated rabbits were challenged via aerosol with human-virulent F. tularensis SCHU S4 that had been cultivated in either Mueller-Hinton broth (MHB) or brain heart infusion (BHI) broth. LVS-vaccinated animals challenged with SCHU S4 that had been cultivated in MHB experienced short febrile periods (median, 3.2 days), limited weight loss (10%) than the unvaccinated controls and median survival times that were not significantly different from those for the unvaccinated controls. These studies highlight the importance of careful characterization and optimization of protocols for aerosol challenge with pathogenic agents.
3. An organotrifluoroborate-based convergent total synthesis of the potent cancer cell growth inhibitory depsipeptides kitastatin and respirantin
Ramsay E Beveridge, Robert A Batey Org Lett. 2014 May 2;16(9):2322-5. doi: 10.1021/ol500484f. Epub 2014 Apr 14.
The total syntheses of the highly cytotoxic neo-antimycin macrocyclic depsipeptide natural products kitastatin and respirantin have been accomplished in a convergent manner using MNBA promoted esterifications and an efficient C- and N-terminus bis-deprotection/HATU promoted macrolactamization. The first examples of using a prenyltrifluoroborate reagent in additions to carbonyl groups are disclosed including a diastereoselective multigram scale montmorillonite K10 catalyzed prenylation of N-Boc-l-leucinal to install the structurally unique gem-dimethyl-β-keto-ester fragment.
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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 ╳
