acosamine and daunosamine

acosamine has been researched along with daunosamine* in 4 studies

Other Studies

4 other study(ies) available for acosamine and daunosamine

ArticleYear
Synthesis and DNA-binding affinity studies of glycosylated intercalators designed as functional mimics of the anthracycline antibiotics.
    Organic & biomolecular chemistry, 2009, Sep-21, Volume: 7, Issue:18

    Anthracycline antibiotics such as daunomycin (Dauno) and doxorubicin (Dox) are well-known clinically used cancer chemotherapeutics, which, among other mechanisms, bind to DNA, thereby triggering a cascade of biological responses leading to cell death. However, anthracyclines are cardiotoxic, and drug resistance develops rapidly, thus limiting their clinical use. We report here the synthesis and DNA-binding affinity of a novel class of functional anthracycline mimetics consisting of an aromatic moiety linked to a carbohydrate (1-12). In the targets, the aromatic core consists of a 2-phenylbenzo[b]furan-3-yl, 2-phenylbenzo[b]thiophen-3-yl, 1-tosyl-2-phenylindol-3-yl, or 2-phenylindol-3-yl group that is bound to one of three aminosugars (daunosamine, acosamine, or 4-amino-2,3,4,6-tetradeoxy-alpha-l-hexopyranoside) via a propargyl linker. The DNA binding affinity of these twelve compounds has been evaluated by using both direct and indirect fluorescence measurements. Compared to Dauno and Dox, the DNA binding affinity of these analogues is weaker. However, both aromatic and aminosugar motifs are critical to DNA binding, with more influence coming from the structural features of the aromatic portion.

    Topics: Animals; Anthracyclines; Anti-Bacterial Agents; Biomimetic Materials; DNA; Drug Design; Glycosides; Glycosylation; Hexosamines; Intercalating Agents; Iodine; Spectrometry, Fluorescence

2009
A stereoselective synthesis of 6,6,6-trifluoro-L-daunosamine and 6,6,6-trifluoro-L-acosamine.
    Organic & biomolecular chemistry, 2006, Jul-21, Volume: 4, Issue:14

    A short synthesis of 6,6,6-trifluoro-L-acosamine 15 and 6,6,6-trifluoro-L-daunosamine 19 has been accomplished. The pyranose ring system of these carbohydrate analogues was formed by a hetero-Diels-Alder reaction of vinylogous imide 11 and ethyl vinyl ether which gave adduct 12a in 40% yield. Hydroboration gave 13 and subsequent hydrogenolytic removal of the (R)-2-phenylethyl chiral auxiliary gave ethyl 6,6,6-trifluoro-L-acosaminide 14. Acid hydrolysis furnished target 15. Glycoside 13 was N-trifluoroacetylated to give 16, the structure was confirmed by single crystal X-ray diffraction. The C-4 stereochemistry of 16 was inverted by Swern oxidation of the 4-OH group, and subsequent borohydride reduction to give 17. Hydrogenolytic removal of the auxiliary gave ethyl-6,6,6-trifluoro-L-daunosaminide 18. Acid hydrolysis provided 19.

    Topics: Fluorine; Hexosamines; Molecular Structure; Stereoisomerism

2006
New stereodivergent approach to 3-amino-2,3,6-trideoxysugars. Enantioselective synthesis of daunosamine, ristosamine, acosamine, and epi-daunosamine.
    Organic letters, 2003, Aug-21, Volume: 5, Issue:17

    [reaction: see text] An enantioselective preparation of the four diastereomeric 3-amino-2,3,6-trideoxy-hexoses, key components of anthracycline antibiotics, has been developed. Sharpless catalytic asymmetric epoxidation of the (2E)-2,5-hexadien-1-ol, regioselective ring opening with azide, followed by convenient functional group transformations, afforded the key aldehydes cis- or trans-6 in any configuration. The diastereoselective addition of methylmetal reagents to these aldehydes followed by ozonolysis gives access in a completely stereocontrolled manner to the four isomeric trideoxyaminosugars.

    Topics: Aldehydes; Azides; Carbohydrate Conformation; Hexosamines; Methylation; Ozone; Stereoisomerism

2003
A short and efficient transformation of rhamnose into activated daunosamine, acosamine, ristosamine and epi-daunosamine derivatives, and synthesis of an anthracycline antibiotic acosaminyl-epsilon-iso-rhodomycinone.
    Carbohydrate research, 2000, Dec-01, Volume: 329, Issue:4

    3-Amino-2,3,6-trideoxyhexopyranoses are essential constituents of most anthracycline antitumour antibiotics. For an investigation of structure-activity relationships, the four diastereomeric amino sugars daunosamine, acosamine, ristosamine, and epi-daunosamine were synthesised in short and efficient routes starting from commercially available rhamnose. Several glycosyl donors were provided and their use was exemplified in the synthesis of acosaminyl-epsilon-isorhodomycinone.

    Topics: Anthracyclines; Antibiotics, Antineoplastic; Doxorubicin; Drug Screening Assays, Antitumor; Hexosamines; Humans; Molecular Structure; Rhamnose; Stereoisomerism; Tumor Cells, Cultured

2000