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Diethylamine → Tylosin 3-Acetate

HRID 1109841
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HRID 1109841 반응식
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]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8021DiethylamineHCID 8857Ethyl AcetateHCID 5280440Tylosin2회HCID 64266063-Acetyltylosin

생성물 1

HCID 71752879Tylosin 3-Acetate

시약·촉매·용매 2

HCID 887
Methanol
용매
HCID 962Water용매

반응 조건

온도
28 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-be586bce4943494b8fbb30bab7931ad4
출처 데이터셋
uspto-grants-1994_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05322937

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