Acetic Acid → FR-179642

HRID 1862191Notes

Reaction equation

HRID 1862191 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.P([O-])(O)(O)=O.[K+].P([O-])([O-])(O)=O.[Na+].[Na+].C(O)(=O)C>CO>[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

5

Reactant 3

HCID 176Acetic 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 sulfateHCID 71312623Disodium hydrogenphosphate potassium dihydrogenphosphate

Product 1

HCID 71714631FR-179642

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 700 μl of the fermentation broth of Streptomyces anulatus No. 4811 obtained in Example 1-1 was added 100 μl of an aqueous solution of Substance FR901379 (100 mg/ml) (10 mg as Substance FR901379; 8.35 μmol) together with 100 μl of methanol and 100 μl of buffer (0.5 M potassium dihydrogen phosphate-disodium hydrogen phosphate buffer; pH 6.0), and the reaction was carried out at 30° C. for 30 minutes. The reaction was then stopped with 1 ml of 4% acetic acid and following addition of 2 ml of methanol, the mixture was filtered through a membrane filter (0.45 μm) to remove the macromolecular protein and other fraction and subjected to HPLC and the acylase activity of the skeletal substance FR179642 produced was monitored and assayed at 210 nm.

Workup

  1. custom4811 obtained in Example 1-1
  2. filtrationthe mixture was filtered through a membrane
  3. filtrationfilter (0.45 μm)
  4. customto remove the macromolecular protein and other fraction

Sources & evidence

ORD record
ord-e0df566f4a90466f878650d7f1dfc00c
Source dataset
uspto-grants-2003_03
Patent number
US06537789B1

Reaction notes

Loading…