100415-25-6 → 100415-25-6

HRID 2371950Notes

Reaction equation

HRID 2371950 reaction equation
[CH3:1][C@@H:2]1[C@@H:40]([OH:41])[CH2:39][C@H:37]2[O:38][C@@H:3]1[CH2:4][CH:5]=[CH:6][C@@H:7]1[O:12][C@H:11]3[C@@H:13]([CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=[CH:20][C:21]([O:23][C@@H:24]4[C@H:56](/[C:57](/[CH3:68])=[CH:58]/[C@@H:59]([CH2:61][CH2:62][CH2:63][CH2:64][C:65]([OH:67])=[O:66])[CH3:60])[O:55][C@@H:27]([CH2:28][CH:29]=[CH:30][CH2:31][CH2:32][CH:33]=[CH:34][C@H:35]([O:43][C@@H:44]5[O:49][C@H:48]([CH2:50][OH:51])[C@@H:47]([OH:52])[C@H:46]([OH:53])[C@H:45]5[OH:54])[C@H:36]2[OH:42])[CH:26]=[CH:25]4)=[O:22])[O:14][C@H:9]([CH2:10]3)[C@H:8]1[CH3:69].[CH3:70][C@@H:71]1[C@@H:109]([OH:110])[CH2:108][C@H:106]2[O:107][C@@H:72]1[CH2:73][CH:74]=[CH:75][C@@H:76]1[O:81][C@H:80]3[C@@H:82]([CH:84]=[CH:85][CH:86]=[CH:87][CH:88]=[CH:89][C:90]([O:92][C@@H:93]4[C@H:114](/[C:115](/[CH3:126])=[CH:116]/[C@@H:117]([CH2:119][CH2:120][CH2:121][CH2:122][C:123]([OH:125])=[O:124])[CH3:118])[O:113][C@@H:96]([CH2:97][CH:98]=[CH:99][CH2:100][CH2:101][CH:102]=[CH:103][C@H:104]([OH:112])[C@@H:105]2[OH:111])[CH:95]=[CH:94]4)=[O:91])[O:83][C@H:78]([CH2:79]3)[C@H:77]1[CH3:127]>>[CH3:1][C@@H:2]1[C@@H:40]([OH:41])[CH2:39][C@H:37]2[O:38][C@@H:3]1[CH2:4][CH:5]=[CH:6][C@@H:7]1[O:12][C@H:11]3[C@@H:13]([CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=[CH:20][C:21]([O:23][C@@H:24]4[C@H:56](/[C:57](/[CH3:68])=[CH:58]/[C@@H:59]([CH2:61][CH2:62][CH2:63][CH2:64][C:65]([OH:67])=[O:66])[CH3:60])[O:55][C@@H:27]([CH2:28][CH:29]=[CH:30][CH2:31][CH2:32][CH:33]=[CH:34][C@H:35]([O:43][C@@H:44]5[O:49][C@H:48]([CH2:50][OH:51])[C@@H:47]([OH:52])[C@H:46]([OH:53])[C@H:45]5[OH:54])[C@H:36]2[OH:42])[CH:26]=[CH:25]4)=[O:22])[O:14][C@H:9]([CH2:10]3)[C@H:8]1[CH3:69].[CH3:70][CH:71]1[CH:109]([OH:110])[CH2:108][CH:106]2[O:107][CH:72]1[CH2:73][CH:74]=[CH:75][CH:76]1[O:81][CH:80]3[CH:82]([CH:84]=[CH:85][CH:86]=[CH:87][CH:88]=[CH:89][C:90]([O:92][CH:93]4[CH:114](/[C:115](/[CH3:126])=[CH:116]/[CH:117]([CH2:119][CH2:120][CH2:121][CH2:122][C:123]([OH:125])=[O:124])[CH3:118])[O:113][CH:96]([CH2:97][CH:98]=[CH:99][CH2:100][CH2:101][CH:102]=[CH:103][CH:104]([OH:112])[CH2:105]2)[CH:95]=[CH:94]4)=[O:91])[O:83][CH:78]([CH2:79]3)[CH:77]1[CH3:127].[CH3:70][C@@H:71]1[C@@H:109]([OH:110])[CH2:108][C@H:106]2[O:107][C@@H:72]1[CH2:73][CH:74]=[CH:75][C@@H:76]1[O:81][C@H:80]3[C@@H:82]([CH:84]=[CH:85][CH:86]=[CH:87][CH:88]=[CH:89][C:90]([O:92][C@@H:93]4[C@H:114](/[C:115](/[CH3:126])=[CH:116]/[C@@H:117]([CH2:119][CH2:120][CH2:121][CH2:122][C:123]([OH:125])=[O:124])[CH3:118])[O:113][C@@H:96]([CH2:97][CH:98]=[CH:99][CH2:100][CH2:101][CH:102]=[CH:103][C@H:104]([OH:112])[C@@H:105]2[OH:111])[CH:95]=[CH:94]4)=[O:91])[O:83][C@H:78]([CH2:79]3)[C@H:77]1[CH3:127]

Participants

5

Reactant 2

HCID 657059100415-25-6HCID 101827001HCID 101827001, compound

Product 3

HCID 657059100415-25-6HCID 6441175sorangicin BHCID 101827001HCID 101827001, compound

Procedure

The fermentation broth is separated from the biomass in conventional manner, e.g. by filtration or centrifugation, and the filtrate is extracted with a water-immiscible, or substantially water-immiscible, solvent, e.g. methylene chloride, chloroform or, preferably, ethyl acetate. The organic phase is evaporated under vacuum, affording a crude extract. This crude extract is partitioned in a two-phase system consisting of two immiscible organic solvents, e.g. methanol/heptane, and the fermentation products, in particular the antibiotics of formula I, become enriched in the polar phase. After removal of the polar solvent by evaporation, the residue is dissolved in dilute ammonia solution and washed with water-immiscible solvent, e.g. diethyl ether. The volatile ammonia is removed under vacuum and the aqueous phase, after acidification with an organic acid, e.g. formic acid or acetic acid, is extracted with one of the water-immiscible, or substantially water-immiscible, solvents mentioned above, e.g. methylene chloride. The resultant antibiotics are subsequently purified by reversed phase chromatography, affording several fractions which may contain sorangioside A and B in admixture or in pure form, and sorangicin A and B in admixture or in pure form. The individual components sorangioside A and B and sorangicin B are obtained by separation of the respective fractions by HPLC, whereas the main component, sorangicin A, can be obtained in crystalline form from the appropriate fraction.

Workup

  1. customThe fermentation broth is separated from the biomass in conventional manner, e.g. by filtration or centrifugation
  2. extractionthe filtrate is extracted with a water-immiscible, or substantially water-immiscible, solvent, e.g. methylene chloride, chloroform
  3. customThe organic phase is evaporated under vacuum
  4. customaffording a crude
  5. extractionextract
  6. extractionThis crude extract
  7. customis partitioned in a two-phase system
  8. customAfter removal of the polar solvent
  9. customby evaporation
  10. dissolutionthe residue is dissolved in dilute ammonia solution
  11. washwashed with water-immiscible solvent, e.g. diethyl ether
  12. customThe volatile ammonia is removed under vacuum
  13. extractionthe aqueous phase, after acidification with an organic acid, e.g. formic acid or acetic acid, is extracted with one of the water-immiscible, or substantially water-immiscible, solvents
  14. customThe resultant antibiotics are subsequently purified by reversed phase chromatography
  15. customaffording several fractions which

Sources & evidence

ORD record
ord-f55c1dff23844d6581544569d8ef923f
Source dataset
uspto-grants-1992_03
Patent number
US05096922

Reaction notes

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