Pyridine → An inositol

HRID 1923451

반응식

HRID 1923451 반응식
[CH:1]1([O:32]P([O-])([O-])=O)[CH:6]([O:7]P([O-])([O-])=O)[CH:5]([O:12]P([O-])([O-])=O)[CH:4]([O:17]P([O-])([O-])=O)[CH:3]([O:22]P([O-])([O-])=O)[CH:2]1[O:27]P([O-])([O-])=O.[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].N1C=CC=CC=1>O>[CH:6]1([OH:7])[CH:5]([OH:12])[CH:4]([OH:17])[CH:3]([OH:22])[CH:2]([OH:27])[CH:1]1[OH:32]

참가 물질

4

반응물 2

HCID 1049PyridineHCID 66391Phytate Persodium

생성물 1

HCID 892An inositol

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
65 °C

실험 절차

Crystalline sodium phytate C (4 g) was dissolved with sonication in water (20 ml) and converted to the free acid by passage through a column of Dowex 50×8-200 ion-exchange resign. The column eluate was adjusted to pH 8 with pyridine and evaporated to dryness. The residue was dissolved in water (30 ml) and pyridine (130 ml) containing N,N-dicyclohexylcarbodiimide (8 g) was added. The reaction mixture was heated to 65° C. for 18 h and evaporated to dryness. The residue was extracted with water (4×10 ml) filtered and the filtrate was evaporated to dryness to give the pentapyridinium Salt of Myo-inositol 1,6:2,3:4,5-Tripyrophosphate (3.355 g, 77% yield). 31P-NMR (D2O) δ: −8.83 & −13.53 (AB, J=22.3 Hz, 2P, ax-eq), −9.82 & −10.00 (AB, J=17.8 Hz, 2P, eq-eq), −10.18 (AB as a singlet, 2P, eq-eq); 1H-NMR (D2O) δ: 8.65 (d, J=5.6 Hz, 10H), 8.48 (dd, J=7.9, 7.9 Hz, 5H), 7.94 (dd, J=7.0, 7.0 Hz, 10H), 5.00 (bd, J=10.5 Hz, 1H), 4.57 (ddd, J=9.6, 9.6, 5.5 Hz, 1H), 4.43-4.36 (m, 2H), 4.30-4.18 (m, 2H); 13C-NMR (D2O) δ: 147.0, 140.9, 127.3, 77.9 (t, J=6.8 Hz), 76.4-76.0 (m), 75.4-75.0 (m), 73.8 (t, J=6.8 Hz), 73.3 (bs), 72.8 (bs). The compound was then dissolved in water (30 ml) and passed through a column Dowex 50W×8 Na+ form. The column eluate was concentrated to dryness to give Hexasodium Salt of Myo-inositol 1,6:2,3:4,5-Tripyrophosphate (2.25 g, 97%) and used for biological experiments in 98.5% purity without any further purification. The impurity is unreacted starting material (or tripyrophosphate hydrolyzed back to starting material). 31P-NMR (D2O) δ: −8.34 & −13.14 (AB, J=21.7 Hz, 2P, ax-eq), −9.53 & −9.70 (AB, J=17.8 Hz, 2P, eq-eq), −9.92 (AB as a singlet, 2P, eq-eq); 1H-NMR (D2O) δ: 5.04 (bd, J=10.5 Hz, 1H), 4.65-4.59 (m, 1H), 4.51-4.36 (m, 2H), 4.32-4.18 (m, 2H); 13C-NMR (D2O) δ: 77.1-76.8 (m), 76.5-76.0 (m), 75.4-75.0 (m), 74.1-73.9 (m), 73.7-73.2 (m), 73.2-72.5 (m).

후처리

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in water (30 ml)
  3. additionpyridine (130 ml) containing N,N-dicyclohexylcarbodiimide (8 g)
  4. additionwas added
  5. customevaporated to dryness
  6. extractionThe residue was extracted with water (4×10 ml)
  7. filtrationfiltered
  8. customthe filtrate was evaporated to dryness

출처 및 근거

ORD 기록
ord-afade9ed855e44889c32812bd01102ba
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178514B2

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