Viriplanin A, a new anthracycline antibiotic of the nogalamycin group. I Isolation, characterization, degradation reactions and biological properties.

A systematic analysis of all naturally-occurring glycosylated bacterial secondary metabolites reported in the scientific literature up through early 2013 is presented. This comprehensive analysis of 15 940 bacterial natural products revealed 3426 glycosides containing 344 distinct appended carbohydrates and highlights a range of unique opportunities for future biosynthetic study and glycodiversification efforts.

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“…Interestingly, these two sugars have also been identified in anthracycline antibiotics (viriplanins A and D, Section 4). 289,290,477 …”

Section: Coumarinsmentioning

confidence: 99%

A comprehensive review of glycosylated bacterial natural products

et al. 2015

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“…26,27 It also exists in several structurally related natural products including arugomycin ( 20 ), 28,29 cororubicin ( 21 ), 30 and viriplanin A ( 22 ). 31,32 Interestingly, these anthracycline-type antibiotics all contain a bicyclo-aminosugar moiety that is attached to the aglycone via a C -glycosidic bond in addition to the typical O -glycosidic linkage.…”

Section: Sugars Containing Oxidized Aminesmentioning

confidence: 99%

The biosynthesis of nitrogen-, sulfur-, and high-carbon chain-containing sugars

2013

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Carbohydrates serve many structural and functional roles in biology. While the majority of monosaccharides are characterized by the chemical composition: (CH2O)n, modifications including deoxygenation, C-alkylation, amination, O- and N-methylation, which are characteristic of many sugar appendages of secondary metabolites, are not uncommon. Interestingly, some sugar molecules are formed via modifications including amine oxidation, sulfur incorporation, and “high-carbon” chain attachment. Most of these unusual sugars have been identified over the past several decades as components of microbially produced natural products, although a few high-carbon sugars are also found in the lipooligosaccharides of the outer cell walls of Gram-negative bacteria. Despite their broad distribution in nature, these sugars are considered “rare” due to their relative scarcity. The biosynthetic steps that underlie their formation continue to perplex researchers to this day and many questions regarding key transformations remain unanswered. This review will focus on our current understanding of the biosynthesis of unusual sugars bearing oxidized amine substituents, thio-functional groups, and high-carbon chains.

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“…15 Another example of a dinitroso compound in which the two nitroso groups act independently of each other is provided by the anthracycline antibiotic viriplanin A [16][17][18][19] an antibiotic with activity against Herpes simplex viruses. In this large molecule (12) the two nitroso groups are each bonded to tertiary carbon atoms in b-pyranoside rings in different sections of the molecule.…”

Section: Non-interacting Dinitroso Compoundsmentioning

confidence: 99%

Dinitroso and polynitroso compounds

Gowenlock

Richter‐Addo

2005

Chem. Soc. Rev.

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The growing interest in the chemistry of C-nitroso compounds (RN=O; R = alkyl or aryl group) is due in part to the recognition of their participation in various metabolic processes of nitrogen-containing compounds. C-Nitroso compounds have a rich organic chemistry in their own right, displaying interesting intra- and intermolecular dimerization processes and addition reactions with unsaturated compounds. In addition, they have a fascinating coordination chemistry. While most of the attention has been directed towards C-nitroso compounds containing a single -NO moiety, there is an emerging area of research dealing with dinitroso and polynitroso compounds. In this critical review, we present and discuss the synthetic routes and properties of these relatively unexplored dinitroso and polynitroso compounds, and suggest areas of further development involving these compounds. (126 references.).

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Viriplanin A, a new anthracycline antibiotic of the nogalamycin group. I Isolation, characterization, degradation reactions and biological properties.

Cited by 27 publications

References 14 publications

A comprehensive review of glycosylated bacterial natural products

A comprehensive review of glycosylated bacterial natural products

The biosynthesis of nitrogen-, sulfur-, and high-carbon chain-containing sugars

Dinitroso and polynitroso compounds

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