Diethylamine → Tylosin 3-Acetate

HRID 1109841

Reaktionsgleichung

Reaktionsgleichung von HRID 1109841
C(OCC)(=O)C.C(NCC)C.CC[C@H]1OC(=O)C[C@@H](O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)[C@@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@](O)(C)C3)[C@H](N(C)C)[C@H]2O)[C@@H](CC=O)C[C@@H](C)C(=O)C=CC(C)=C[C@@H]1CO[C@@H]1O[C@H](C)[C@@H](O)[C@@H](OC)[C@H]1OC.[CH3:76][CH2:77][CH:78]1[O:95][C:93](=[O:94])[CH2:92][CH:91]([O:96][C:97]([CH3:99])=[O:98])[CH:90]([CH3:100])[CH:89]([O:101][CH:102]2[O:107][CH:106]([CH3:108])[CH:105]([O:109][CH:110]3[O:115][CH:114]([CH3:116])[CH:113]([OH:117])[C:112]([OH:119])([CH3:118])[CH2:111]3)[CH:104]([N:120]([CH3:122])[CH3:121])[CH:103]2[OH:123])[CH:88]([CH2:124][CH:125]=[O:126])[CH2:87][CH:86]([CH3:127])[C:84](=[O:85])[CH:83]=[CH:82][C:81]([CH3:128])=[CH:80][CH:79]1[CH2:129][O:130][CH:131]1[O:136][CH:135]([CH3:137])[CH:134]([OH:138])[CH:133]([O:139][CH3:140])[CH:132]1[O:141][CH3:142]>CO.O>[CH3:76][CH2:77][C@H:78]1[O:95][C:93](=[O:94])[CH2:92][C@@H:91]([O:96][C:97]([CH3:99])=[O:98])[C@H:90]([CH3:100])[C@@H:89]([O:101][C@@H:102]2[O:107][C@H:106]([CH3:108])[C@@H:105]([O:109][C@@H:110]3[O:115][C@@H:114]([CH3:116])[C@H:113]([OH:117])[C@@:112]([OH:119])([CH3:118])[CH2:111]3)[C@H:104]([N:120]([CH3:122])[CH3:121])[C@H:103]2[OH:123])[C@@H:88]([CH2:124][CH:125]=[O:126])[CH2:87][C@@H:86]([CH3:127])[C:84](=[O:85])[CH:83]=[CH:82][C:81]([CH3:128])=[CH:80][CH:79]1[CH2:129][O:130][C@@H:131]1[O:136][C@H:135]([CH3:137])[C@@H:134]([OH:138])[C@@H:133]([O:139][CH3:140])[C@H:132]1[O:141][CH3:142]

Komponenten

7

Edukt 4

HCID 8021DiethylamineHCID 8857Ethyl AcetateHCID 5280440Tylosin2×HCID 64266063-Acetyltylosin

Produkt 1

HCID 71752879Tylosin 3-Acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
28 °C

Versuchsvorschrift

In a 250 ml-Erlenmeyer flask (containing coil) containing 50 ml of a production medium (0.5% soluble starch, 5% glucose, 0.5% yeast extract, 1.0% malt extract, and 5 μg/ml of thiopeptine) was inoculated a platinum loopful of AB10ΔB1 strain, and cultivated by shaking culture at 28° C. for 21 days. Then, to a portion (1 ml) of the culture medium were added 0.2 g of K2HPO4 and 0.2 ml of toluene, and the mixture was stirred vigorously to effect extraction. After centrifugation (3,000 rpm, 10 minutes), the toluene layer, which is an upper layer, was taken out and subjected to thin layer chromatography. As the thin layer chromatography plate was used Art 5715 (produced buy Merck Co.) and the developer used was ethyl acetate (75 ml):diethylamine (1.5 ml):water (1.5 ml):methanol (0.75 ml). After drying it, the plate was analyzed at 280 nm using Chromato Scanner (CS-930, produced by Shimazu Seisakusho), and the positions of spots were confirmed by color development by immersing the plate in 10% H solution and heating it at 105° C. for 5 minutes. Tylosin had an Rf (relative mobility) value of 0.62 while the product by the transformed strain contained 3-acetyltylosin at Rf=0.68 in addition to tylosin.

Aufarbeitung

  1. additionIn a 250 ml-Erlenmeyer flask (containing coil)
  2. additioncontaining
  3. extraction50 ml of a production medium (0.5% soluble starch, 5% glucose, 0.5% yeast extract, 1.0% malt extract, and 5 μg/ml of thiopeptine)
  4. additionThen, to a portion (1 ml) of the culture medium were added 0.2 g of K2HPO4 and 0.2 ml of toluene
  5. stirringthe mixture was stirred vigorously
  6. extractionextraction
  7. customAfter centrifugation (3,000 rpm, 10 minutes)
  8. customArt 5715 (produced buy Merck Co.)
  9. customAfter drying it
  10. customChromato Scanner (CS-930, produced by Shimazu Seisakusho)
  11. temperatureheating it at 105° C. for 5 minutes

Quellen und Nachweise

ORD-Eintrag
ord-be586bce4943494b8fbb30bab7931ad4
Quelldatensatz
uspto-grants-1994_06
Patentnummer
US05322937

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