Methanol → 7-Xylosyl-10-deacetylbaccatin III

HRID 1940469Notes

Reaction equation

HRID 1940469 reaction equation
[CH3:1][C:2]1[C@@H:19]([O:20]C([C@H](O)[C@@H](NC(C2C=CC=CC=2)=O)C2C=CC=CC=2)=O)[CH2:18][C@:14]2([OH:41])[C:15]([CH3:17])([CH3:16])[C:3]=1[C@@H:4]([OH:68])[C:5]([C@@:7]1([CH3:67])[C@@H:12]([C@@H:13]2[O:42][C:43]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:44])[C@:11]2([O:53][C:54]([CH3:56])=[O:55])[CH2:51][O:52][C@@H:10]2[CH2:9][C@@H:8]1[O:57][C@@H:58]1[O:63][CH2:62][C@@H:61]([OH:64])[C@H:60]([OH:65])[C@H:59]1[OH:66])=[O:6].CO.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O>[CH3:1][C:2]1[C@@H:19]([OH:20])[CH2:18][C@:14]2([OH:41])[C:15]([CH3:16])([CH3:17])[C:3]=1[C@@H:4]([OH:68])[C:5]([C@@:7]1([CH3:67])[C@H:12]([C@@H:13]2[O:42][C:43]([C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)=[O:44])[C@:11]2([O:53][C:54]([CH3:56])=[O:55])[CH2:51][O:52][C@@H:10]2[CH2:9][C@@H:8]1[O:57][C@@H:58]1[O:63][CH2:62][C@@H:61]([OH:64])[C@H:60]([OH:65])[C@H:59]1[OH:66])=[O:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 62657Potassium Phosphate, TribasicHCID 4678379610-Deacetyltaxol 7-Xyloside

Product 1

HCID 53153567-Xylosyl-10-deacetylbaccatin IIIYield 103%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Cells were prepared as described in Example 4. 1 mg 7-xylosyl-10-deacetyltaxol, 200 mg (108 milliunits) C-13 deacylase (described in Example 4), 0.2 ml methanol, 0.2 ml 1 M potassium phosphate buffer pH 7, and 3.6 ml water were mixed end-over-end at 48 rpm for 17 hours at 24° C. After 15 hours, HPLC analysis by Method 1 showed complete removal of C-13 side chain from the substrate. 2 ml of the solution now containing 7-xylosyl-10-deacetylbaccatin-III was added to 1 ml of the above Moraxella sp. cells (0.24 g wet cell weight) in 50 mM potassium phosphate buffer pH 7 and mixed end-over-end for 24 hours at 48 rpm. Reaction mixtures were extracted with 6 ml CH2Cl2. Extracts were dried and redissolved in methanol for HPLC analysis by Method 1. 0.099 mg/ml 10-deacetylbaccatin-III was found (103% yield based on initial 7-xylosyl-10-deacetyltaxol concentration).

Workup

  1. customCells were prepared
  2. customHPLC analysis by Method 1 showed complete removal of C-13 side chain from the substrate
  3. addition2 ml of the solution now containing 7-xylosyl-10-deacetylbaccatin-III was added to 1 ml of the above Moraxella sp
  4. additioncells (0.24 g wet cell weight) in 50 mM potassium phosphate buffer pH 7 and mixed end-over-end for 24 hours at 48 rpm
  5. customReaction mixtures
  6. extractionwere extracted with 6 ml CH2Cl2
  7. customExtracts were dried
  8. dissolutionredissolved in methanol for HPLC analysis by Method 1
  9. concentration(103% yield based on initial 7-xylosyl-10-deacetyltaxol concentration)

Sources & evidence

ORD record
ord-65cf0ffbe56d42739b07770481d8d9e5
Source dataset
uspto-grants-1997_12
Patent number
US05700669

Reaction notes

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