Trisodium citrate → FR-179642

HRID 1857308Notes

Reaction equation

HRID 1857308 reaction equation
CCCCCCCCCCCCCCCC([NH:18][C@@H:19]1[C:50](=[O:51])[NH:49][C@@H:48]([C@H:52]([OH:54])[CH3:53])[C:46](=[O:47])[N:45]2[C@@H:41]([CH2:42][C@@H:43]([OH:55])[CH2:44]2)[C:39](=[O:40])[NH:38][C@@H:37]([C@H:56]([OH:71])[C@@H:57]([OH:70])[C:58]2[CH:59]=[CH:60][C:61]([OH:69])=[C:62]([O:64][S:65]([OH:68])(=[O:67])=[O:66])[CH:63]=2)[C:35](=[O:36])[NH:34][C@@H:33]([C@H:72]([OH:77])[CH2:73][C:74]([NH2:76])=[O:75])[C:31](=[O:32])[N:30]2[C@@H:26]([C@@H:27]([OH:79])[C@@H:28]([CH3:78])[CH2:29]2)[C:24](=[O:25])[NH:23][C@@H:22]([OH:80])[C@H:21]([OH:81])[CH2:20]1)=O.C([O-])(=O)CC(CC([O-])=O)(C([O-])=O)O.[Na+].[Na+].[Na+].ClC(Cl)(Cl)C(O)=O>>[CH3:78][C@@H:28]1[C@H:27]([OH:79])[C@H:26]2[C:24]([NH:23][C@H:22]([OH:80])[C@H:21]([OH:81])[CH2:20][C@H:19]([NH2:18])[C:50]([NH:49][C@@H:48]([C@H:52]([OH:54])[CH3:53])[C:46]([N:45]3[C@H:41]([C:39]([NH:38][C@@H:37]([C@H:56]([OH:71])[C@@H:57]([OH:70])[C:58]4[CH:59]=[CH:60][C:61]([OH:69])=[C:62]([O:64][S:65]([OH:68])(=[O:67])=[O:66])[CH:63]=4)[C:35]([NH:34][C@@H:33]([C@H:72]([OH:77])[CH2:73][C:74]([NH2:76])=[O:75])[C:31](=[O:32])[N:30]2[CH2:29]1)=[O:36])=[O:40])[CH2:42][C@@H:43]([OH:55])[CH2:44]3)=[O:47])=[O:51])=[O:25]

Participants

4

Reactant 3

HCID 6224Trisodium citrateHCID 6421Trichloroacetic AcidHCID 44352613[5-[(1S,2S)-2-[(3S,6S,9S,11R,15S,18S,20R,21S,24S,25S,26S)-3-[(1R)-3-amino-1-hydroxy-3-oxopropyl]-18-(hexadecanoylamino)-11,20,21,25-tetrahydroxy-15-[(1R)-1-hydroxyethyl]-26-methyl-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexazatricyclo[22.3.0.09,13]heptacosan-6-yl]-1,2-dihydroxyethyl]-2-hydroxyphenyl] hydrogen sulfate2×

Product 1

HCID 71714631FR-179642

Procedure

To 7 ml of the fermentation broth of Oidiodendron sp. No. 30084 obtained in Example 1-1 was added 1 ml of an aqueous solution (20 mg/ml) of FR901379 Substance (20 mg as FR901379 Substance; 16.7 μmol) as well as 2 ml of a buffer (0.2M sodium citrate buffer, pH 4.0), and the reaction was carried out at 30° C. for 3 hours. The reaction was then stopped by adding 0.4M trichloroacetic acid and centrifuged at low speed to remove precipitated high molecular weight protein and other impurities. The FR179642 Substance produced was subjected to HPLC and monitored at 210 nm to determine the acylase activity.

Workup

  1. custom30084 obtained in Example 1-1
  2. customto remove
  3. customprecipitated high molecular weight protein and other impurities

Sources & evidence

ORD record
ord-e5c32cf376b54e578bc823212e96bc87
Source dataset
uspto-grants-2000_11
Patent number
US06146872

Reaction notes

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