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D-(+)-Digitoxose
≥99.0% (TLC)
Synonym(e):
2,6-Dideoxy-D-ribo-hexose
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About This Item
Empirische Formel (Hill-System):
C6H12O4
CAS-Nummer:
Molekulargewicht:
148.16
Beilstein:
1721555
MDL-Nummer:
Assay
≥99.0% (TLC)
Optische Aktivität
[α]20/D +48±2°, c = 1% in H2O
mp (Schmelzpunkt)
98-100 °C
SMILES String
C[C@H]1OC(O)C[C@H](O)[C@@H]1O
InChI
1S/C6H12O4/c1-3-6(9)4(7)2-5(8)10-3/h3-9H,2H2,1H3/t3-,4+,5?,6-/m1/s1
InChIKey
FDWRIIDFYSUTDP-WGDKFINWSA-N
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Biochem./physiol. Wirkung
The natural glycoside digitoxin contains a trisaccharide component made up of digitoxose monosaccharides. A modified monosaccharide digitoxin (with a single digitoxose moiety) was found to have greater anti-proliferative effects on various human non-small cell lung cancer cell lines than intact digitoxin.
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D F Brown et al.
Experientia, 39(9), 979-984 (1983-09-15)
The effect of digitoxose (DIG) on food intake, gold thioglucose (GTG) lesion formation in the ventromedial hypothalamus (VMH), and VMH glucose oxidation in vitro was investigated in mice. DIG significantly decreased the amount of food ingested during the day compared
Amélia P Rauter et al.
Carbohydrate research, 340(2), 191-201 (2005-01-11)
Synthesis of alkyl 2,6-dideoxy-L-arabino-hexopyranosides was accomplished by the reaction of 1,5-anhydro-2,6-dideoxy-L-arabino-hex-1-enitol with fatty alcohols in dichloromethane, catalyzed by triphenylphosphine hydrobromide. Reaction with octanol and dodecanol gave the corresponding alpha-glycosides in 50% and 42% yield, the beta-glycosides in 20% and 21%
Shannon C Timmons et al.
Carbohydrate research, 342(18), 2695-2704 (2007-10-24)
As deoxysugars are integral components of many natural products, the development of efficient chemical and enzymatic routes to prepare these compounds is of particular interest. Herein, we report a comparison of several synthetic methodologies used to prepare protected derivatives of
W M Rockey et al.
Carbohydrate research, 335(4), 261-273 (2001-10-12)
Extensive variations of the ring structures of three deoxyaldohexopyranoses, L-fucose, D-quinovose, and L-rhamnose, and four dideoxyaldohexopyranoses, D-digitoxose, abequose, paratose, and tyvelose, were studied by energy minimization with the molecular mechanics algorithm MM3(92). Chair conformers, 4C(1) in D-quinovose and the equivalent
Rachel L Kubiak et al.
Biochemistry, 50(26), 5905-5917 (2011-05-24)
l-Digitoxose is an unusual dideoxysugar found attached to various pharmacologically active natural products, including the antitumor antibiotic tetrocarcin A and the antibiotics kijanimicin and jadomycin B. Six enzymes are required for its production starting from glucose 1-phosphate. Here we describe
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