반응 #2503593

ord-dc18771ad84b4588bca7181e52339f02

반응 방정식

OC1C(O)C(O)C(O)C(O)C1O
L-chiro-inositol
OC[C@H]1O[C@H](OC2[C@@H](O)[C@@H](O)C(O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@H]1O
Fagopyritol A1
OC[C@H]1O[C@H](OC2[C@@H](O)[C@H](O)C(O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@H]1O
Fagopyritol B1
OC1C(O)C(O)C(O)C(O)C1O
D-chiro-inositol
→
O=C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO
D-galactose
OC[C@H]1O[C@H](OC2[C@@H](O)[C@@H](O)C(O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@H]1O
Fagopyritol A1
OC1C(O)C(O)C(O)C(O)C1O
D-chiro-inositol

반응물

OC1C(O)C(O)C(O)C(O)C1O
L-chiro-inositol
OC[C@H]1O[C@H](OC2[C@@H](O)[C@@H](O)C(O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@H]1O
Fagopyritol A1
OC[C@H]1O[C@H](OC2[C@@H](O)[C@H](O)C(O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@H]1O
Fagopyritol B1
OC1C(O)C(O)C(O)C(O)C1O
D-chiro-inositol

시약

없음

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타Results
  2. 2
    추출Buckwheat bran was extracted with 50% EtOH
  3. 3
    추출the resulting extract
  4. 4
    기타chromatographed on carbon-Celite, 1:1 (w/w)
  5. 5
    기타to purify Fagopyritol A1
  6. 6
    기타Fagopyritol B1 was also purified from the same sample for comparison
  7. 7
    기타Per(pentafluoropropionates) of chiro-inositol from acid hydrolysis of Fagopyritol A1 and Fagopyritol B1

실험 절차

Results. Buckwheat bran was extracted with 50% EtOH, and the resulting extract chromatographed on carbon-Celite, 1:1 (w/w), to purify Fagopyritol A1. Fagopyritol B1 was also purified from the same sample for comparison. Per(pentafluoropropionates) of chiro-inositol from acid hydrolysis of Fagopyritol A1 and Fagopyritol B1 co-chromatographed on a chiral column with authentic D-chiro-inositol, but not with authentic L-chiro-inositol. Hydrolysis of Fagopyritol A1 and Fagopyritol B1 produced D-galactose and D-chiro-inositol in mole ratios of 1.01:1.00 for Fagopyritol A1 and 1.03:1.00 for Fagopyritol B11. Free D-chiro-inositol was obtained by acid hydrolysis of a mixture of Fagopyritol A1 and Fagopyritol B1 followed by purification on a carbon-Celite column. Fagopyritol A1 and Fagopyritol B1 were hydrolyzed by β-D-galactosidase, but not by β-D-galactosidase, demonstrating an α-D-galactopyranosyl linkage.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US06825173B2uspto-grants-2004_11