Assignment of the Liposidomycin Diazepanone Stereochemistry

Knapp, Spencer; Morriello, Gregori J.; Nandan, Santosh; Emge, Thomas J.; Doss, George A.; Mosley, Ralph T.; Chen, Lijian

doi:10.1021/jo010355g

Cited by 34 publications

(21 citation statements)

References 19 publications

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“…More than 8 groups have studied the total synthesis of LPMs. [123][124][125][126][127][128][129][130][131][132][133][134][135][136][137][138][139][140] Difficulty in the synthesis of this class of molecules may lie with the introduction of 5-aminoribose moiety found in CPZs and LPMs after construction of a uridyldiazepanone moiety because the tertiary amine contained in the diazepanone structure inhibited the usual ribosylation promoted by Lewis acid. In addition, CPZs and LPMs would be sensitive to basic conditions because they contain a b-heterosubstituted carboxyl moiety.…”

Section: -110)mentioning

confidence: 99%

Fine Synthetic Nucleoside Chemistry Based on Nucleoside Natural Products Synthesis

Ichikawa

2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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Synthetic nucleoside chemistry based on nucleoside natural products synthesis were described. First, a samarium diiodide (SmI 2 )-promoted aldol reaction with the use of a a-phenylthioketone as an enolate was developed. The characteristics of this reaction are that the enolate can be regioselectively generated and the aldol reaction proceeds under near neutral condition. This reaction is proved to be a powerful reaction for the synthesis of complex nucleoside natural products, and herbicidin B and fully protected tunicaminyluracil, which were undecose nucleoside natural products, were synthesized. Next, the synthetic methodology of the caprazamycins, which are promising antibacterial nucleoside natural products, was also developed by the strategy including b bselective ribosylation without using a neighboring group participation. Our synthetic route provided a range of key analogues with partial structures to define the pharmacophore. Simplification of the caprazamycins was further pursued to develop diketopiperazine analogs.

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Section: -110)mentioning

confidence: 99%

Fine Synthetic Nucleoside Chemistry Based on Nucleoside Natural Products Synthesis

Ichikawa

2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…3.4) has been investigated by the groups of Knapp [81][82][83] and Ubukata [84,85] through chemical synthesis. Recent studies have indicated that the configuration at C-5' and C-6' are both S [83], and the configuration at C-2''' and C-3''' are also both S [85].…”

Section: Bmentioning

confidence: 99%

Phospho-MurNAc-Pentapeptide Translocase (MraY) as a Target for Antibacterial Agents and Antibacterial Proteins

Bugg¹,

Lloyd²,

Roper³

2006

IDDT

124

101

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Phospho-MurNAc-pentapeptide translocase (MraY, translocase I) catalyses the first step of the lipid-linked cycle of reactions of bacterial peptidoglycan biosynthesis. MraY is the target for five families of nucleoside antibacterial natural products: the tunicamycins, the mureidomycins (also pacidamycins, napsamycins), the liposidomycins, the muraymycins, and the capuramycins. Recent structure-activity studies on these families have led to the identification of active pharmacophores, and insight into their mechanisms of action. This step of peptidoglycan biosynthesis is also the target for the bacteriolytic E protein from bacteriophage phiX174, and for cyclic peptides of the amphomycin family which complex the undecaprenyl phosphate co-substrate. The mechanisms of enzyme inhibition by these agents are discussed, and the state of knowledge regarding the transmembrane structure, active site, and catalytic mechanism of MraY. The availability of high throughput assays and prospects of MraY as an antibacterial target are also discussed.

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“…The configuration of the double bonds of the lipid moiety of liposidomycin A I is cis [22]. The stereoselective synthesis of the disaccharide and 1,4-diazepan-3-one fragments and their comparison with the degradation products of liposidomycin have enabled the determination of configurations [23,24].…”

Section: Natural Disaccharide Nucleosidesmentioning

confidence: 99%

Disaccharide Nucleosides and their Incorporation into Oligonucleotides

Efimtseva¹,

Kulikova²,

Mikhailov³

2007

COC

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The review summarizes structural features, biological activity and synthetic methods of disaccharide nucleosides. In the first part the structures of natural disaccharide nucleosides are presented. The consequent part deals with general methods of synthesis of these compounds -formation of new N-and O-glycosidic bonds. Recent achievements in the preparation of disaccharide nucleosides from natural nucleosides are discussed. The last part is devoted to the synthesis and properties of oligonucleotides containing disaccharide nucleosides.Disaccharide nucleosides belong to an important group of natural compounds forming poly(ADP-ribose) and found in tRNA, antibiotics, and other physiologically active compounds. To date about a hundred disaccharide nucleoside and related derivatives have been isolated from various natural sources. These compounds contain an extra carbohydrate residue linked to one of the nucleoside hydroxyl groups via an O-glycosidic bond. The presence of a disaccharide residue and a heterocyclic base makes their properties similar to those of carbohydrates and nucleosides. These compounds manifest a broad spectrum of biological (including antibacterial, fungicidal, herbicidal, antitumour and antiviral) activities. The review by Lerner [1] published in 1991 provides a detailed description of the structures of disaccharide nucleoside antibiotics and the approaches to their synthesis. Some of the published data on the synthesis of complex nucleoside antibiotics were summarized by Knapp [2]. Since that time, many new publications devoted to this problem have appeared in the current literature. In our recent publiccations physicochemical properties [3], structure and general synthetic approaches to the synthesis [4] of disaccharide nucleosides were reviewed. Here we describe structural peculiarities of disaccharide nucleosides and summarize our recent data on their synthesis and incorporation into oligonucleotides (ONs). NATURAL DISACCHARIDE NUCLEOSIDESThe structures of disaccharide nucleosides are extremely diverse [5,6] and their elucidation is a rather complicated task. In addition to a heterocyclic base and two mono-saccharide residues, these compounds contain various functional substituents, such as acyl and alkyl groups as well as phosphate and sulfate residues, fatty acids, amino acids, peptides and additional sugars. Their degradation by acid and alkaline hydrolysis or methanolysis, periodate oxidation and subsequent reduction yields fragments the structures of which can be established by physicochemical methods. At present, the structures of many complex antibiotics are determined mainly by NMR spectroscopy and mass spectrometry.According to their structure natural disaccharide nucleosides may be divided into three main groups. Disaccharide nucleosides belonging to the first two groups contain natural purine nucleoside. In the first group additional ribofuranosyl residue is attached via O-glycosidic bond to the adenosine or guanosine. Most of these derivatives were found in biopolymers. 2 (3 )-O-...

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Assignment of the Liposidomycin Diazepanone Stereochemistry

Cited by 34 publications

References 19 publications

Fine Synthetic Nucleoside Chemistry Based on Nucleoside Natural Products Synthesis

Fine Synthetic Nucleoside Chemistry Based on Nucleoside Natural Products Synthesis

Phospho-MurNAc-Pentapeptide Translocase (MraY) as a Target for Antibacterial Agents and Antibacterial Proteins

Disaccharide Nucleosides and their Incorporation into Oligonucleotides

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