37040
D-(+)-Digitoxose
≥99.0% (TLC)
Synonym(s):
2,6-Dideoxy-D-ribohexose
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About This Item
Empirical Formula (Hill Notation):
C6H12O4
CAS Number:
Molecular Weight:
148.16
Beilstein:
1721555
MDL number:
Assay
≥99.0% (TLC)
optical activity
[α]20/D +48±2°, c = 1% in H2O
mp
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
InChI key
FDWRIIDFYSUTDP-WGDKFINWSA-N
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Biochem/physiol Actions
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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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
Sumei Li et al.
Organic letters, 15(6), 1374-1377 (2013-02-26)
The identification of a lobophorin biosynthetic gene cluster from the deep-sea derived Streptomyces sp. SCSIO 01127 reveals a paradigm of three glycosyltransferases (GTs) LobG1-LobG3 being responsible for appending four sugars. Characterization of five differentially glycosylated metabolites from three GT gene-inactivation
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
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
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