Methanol → epothilone E

HRID 1830996Notes

Reaction equation

HRID 1830996 reaction equation
[CH3:1][C:2]1[S:6][CH:5]=[C:4](/[CH:7]=[C:8](/[C@H:10]2[O:28][C:26](=[O:27])[CH2:25][C@H:24]([OH:29])[C:23]([CH3:31])([CH3:30])[C:21](=[O:22])[C@H:20]([CH3:32])[C@@H:19]([OH:33])[C@@H:18]([CH3:34])[CH2:17][CH2:16][CH2:15][C@H:13]3[O:14][C@H:12]3[CH2:11]2)\[CH3:9])[N:3]=1.C[OH:36]>>[CH3:34][C@@H:18]1[C@H:19]([OH:33])[C@@H:20]([CH3:32])[C:21](=[O:22])[C:23]([CH3:31])([CH3:30])[C@@H:24]([OH:29])[CH2:25][C:26](=[O:27])[O:28][C@H:10](/[C:8](/[CH3:9])=[CH:7]/[C:4]2[N:3]=[C:2]([CH2:1][OH:36])[S:6][CH:5]=2)[CH2:11][C@@H:12]2[O:14][C@@H:13]2[CH2:15][CH2:16][CH2:17]1

Participants

3

Reactant 2

HCID 887MethanolHCID 448799Epothilone A

Product 1

HCID 9806341epothilone E

Procedure

The concentrated culture is transferred to a 4 liter bioreactor and a methanolic solution of 1 g of epothilone A in 10 ml of methanol is added. The culture is then cultured further for a period of time of 21.5 h. The temperature is 32° C., the stirrer speed is 455 rpm and the introduction of air takes place at 6 l/min. At the time of harvesting, 100 ml of XAD is added and the mixture is incubated further for 1 h. The XAD is separated from the cells by screening and exhaustively eluted with methanol. The concentrated eluate is analysed by means of HPLC.

Workup

  1. customis 32° C.
  2. additionAt the time of harvesting, 100 ml of XAD is added
  3. waitthe mixture is incubated further for 1 h
  4. customThe XAD is separated from the cells
  5. washexhaustively eluted with methanol

Sources & evidence

ORD record
ord-982394f40b7d466ab77393233dc66ef7
Source dataset
uspto-grants-2006_06
Patent number
US07067544B2

Reaction notes

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