Mannosidohydroxystreptomycin fromStreptomyces sp.

Arcamone, F; Cassinelli, Giuseppe; D'Amico, Giovanni; Orezzi, P.

doi:10.1007/bf02144377

Cited by 18 publications

(13 citation statements)

References 5 publications

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“…Daunosamine, 3-amino-2,6 dideoxy-l-lyxo-hexose is the natural aminosugar present in all anthracycline glycosides produced by the strains belonging to the species Streptomyces peucetius, the original producer of the daunorubicin group of antibiotics, and related strains [3]. It has never been identified as a constituent of other anthracyclines nor of any natural glycoside.…”

Section: Design Of the Disaccharide Doxorubicin Analoguesmentioning

confidence: 99%

“…The final products are characterized by varied molecular structures, further diversified by the different glycosylation patterns typical for the different families of final glycosides. In the case of the anthracyclines, the pattern of glycosylation is a consequence, both in terms of the nature of the sugar moieties as well as of the position of the substitution, of the genetic constitution of the producing microbial strains [3][4][5][6]. The antitumor activity of a biosynthetic anthracycline and its chemical relationship with the glycosidic pigments previously studied and described by different authors was first reported in 1959 [7].…”

Section: Introductionmentioning

confidence: 99%

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Sabarubicin

Arcamone

2007

Topics in Current Chemistry

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Disaccharide derivatives in the daunorubicin and in the 4-demethoxy (idarubicin) series in whichthe first sugar moiety linked to the aglycone is a non-aminated sugar, namely 2-deoxy-L-rhamnose or 2-deoxy-L-fucose andthe second moiety is daunosamine, have been obtained upon synthesis of the appropriate activated sugarintermediate and glycosylation of the corresponding aglycones. The compounds containing 2-deoxy-L-fucose exhibit superior pharmacological properties with respect to thestereoisomers containing 2-deoxy-L-rhamnose. The doxorubicinanalog 7-O-(α-L-daunosaminyl-α(1-4)-2-deoxy-L-fucosyl)-4-demethoxy-adriamycinone (sabarubicin) was prepared startingfrom 14-acetoxyidarubicinone. Solution properties and molecular interactions are compared with thoseof doxorubicin. Sabarubicin exhibits a superior antitumor efficacy, presumably related to theactivation of p53-independent apoptosis. A number of sabarubicin analogues have also been synthesized.

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Section: Design Of the Disaccharide Doxorubicin Analoguesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Sabarubicin

Arcamone

2007

Topics in Current Chemistry

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“…Anthracyclines are a group of drugs used in cancer chemotherapy [65]. Daunorubicin and doxorubicin produced by S. peucetius have been effective against most types of cancer [66].…”

Section: Polyketidesmentioning

confidence: 99%

Natural Products of Actinobacteria Derived from Marine Organisms

Karuppiah

Sun

2016

Studies in Natural Products Chemistry

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“…The most common is L-daunosamine, present in the carbohydrate moieties of the anthracycline family of antibiotics. 2 These include clinically useful agents for the medical treatment of human cancer such as daunorubicin, doxorubicin, and synthetic idarubicin ( Figure 2). 3,4 L-Acosamine, a C-4 epimer of L-daunosamine, was isolated from actinoidin, a vancomycin-type antibiotic.…”

Section: Introductionmentioning

confidence: 99%

“…Less toxic than doxorubicin, this compound is currently available for the medicinal treatment of advanced cancers. [2][3][4][5] L-Ristosamine is a component of the water-soluble glycoprotein ristomycin, a member of the vancomycin family of antibiotics, 1,6 used to diagnose variants of von Willebrand disease. 7 The fourth theoretically possible 3-amino-2,3,6-trideoxy-L-hexose, with the L-xylo configuration, has not been found in nature so far.…”

Section: Introductionmentioning

confidence: 99%

Methyl 3-Amino-2,3,6,-trideoxy-l-hexopyranosides in DFT Level Theory Conformational Studies

Nowacki

Liberek

2008

J. Phys. Chem. A

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Geometry optimizations at the B3LYP level of density functional theory are reported for the (1)C4 and (4)C1 conformations of four theoretically possible alpha and beta methyl 3-amino-2,3,6-trideoxy-L-hexopyranosides. The Gibbs free energies, relative Gibbs free energies, and geometry parameters are presented for all the optimized structures. Conformational analysis of the pyranose ring is performed for each stereoisomer on the basis of calculated rotamer populations. It is demonstrated that the alpha/beta-L-arabino, alpha/beta-L-lyxo, and alpha-L-ribo stereoisomers adopt the (1)C4 conformation, whereas beta-L-ribo and alpha/beta-L-xylo stereoisomers remain in (1)C4 <==> (4)C1 conformational equilibrium. The preference of the alpha over the beta anomers is due to the endo-anomeric effect. The factors affecting the stability of pyranose ring conformations are discussed, as is the influence of hydrogen bonds on the orientation of the hydroxyl and amino groups. Figures of the most stable conformers are presented.

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Mannosidohydroxystreptomycin fromStreptomyces sp.

Cited by 18 publications

References 5 publications

Sabarubicin

Sabarubicin

Natural Products of Actinobacteria Derived from Marine Organisms

Methyl 3-Amino-2,3,6,-trideoxy-l-hexopyranosides in DFT Level Theory Conformational Studies

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