Synthesis of nucleoside aminooxy acids

Gong, Yan; Peyrat, Sandrine; Sun, Hongbin; Xie, Juan

doi:10.1016/j.tet.2011.06.105

Cited by 14 publications

(15 citation statements)

References 44 publications

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“…We have designed nucleoside aminooxy acids as novel building blocks for the development of stable oligonucleotide mimetics [35]. Replacement of the ionic phosphodiester by the neutral N -oxyamide linkage would not only increase its cellular permeability but also enhance its resistance to extra- and intracellular nucleases degradation.…”

Section: O-aminooxy Nucleosidesmentioning

confidence: 99%

Synthesis of O-Amino Sugars and Nucleosides

Chen

Xie

2018

Molecules

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Nucleic acids and carbohydrates are essential biomolecules involved in numerous biological and pathological processes. Development of multifunctional building blocks based on nucleosides and sugars is in high demand for the generation of novel oligonucleotide mimics and glycoconjugates for biomedical applications. Recently, aminooxyl-functionalized compounds have attracted increasing research interest because of their easy derivatization through oxime ligation or N-oxyamide formation reactions. Various biological applications have been reported for O-amino carbohydrate- and nucleoside-derived compounds. Here, we report our efforts in the design and synthesis of glyco-, glycosyl, nucleoside- and nucleo-aminooxy acid derivatives from readily available sugars and amino acids, and their use for the generation of N-oxyamide-linked oligosaccharides, glycopeptides, glycolipids, oligonucleosides and nucleopeptides as novel glycoconjugates or oligonucleotide mimics. Delicate and key points in the synthesis will be emphasized.

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Section: O-aminooxy Nucleosidesmentioning

confidence: 99%

Synthesis of O-Amino Sugars and Nucleosides

Chen

Xie

2018

Molecules

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“…As part of a continuing program on the synthesis of sugarand nucleoside-derived aminooxy acids, [13][14][15][16][17] we report herein the synthesis of nucleo aminooxy acid derivatives with thymine or cytosine connected to the side chain of a β-aminooxy acid through either an amide or a triazole linkage (Figure 1). To the best of our knowledge, nucleo aminooxy acids have not been previously reported in the literature.…”

Section: 12mentioning

confidence: 99%

“…11,12 It would therefore be interesting to synthesize nucleo aminooxy acids containing nucleobases on the side chain of aminooxy acids in order to study the secondary structure and DNA/RNA binding properties of the corresponding Noxy nucleopeptides, since both the N-oxy peptide and the nucleobases could contribute to structure organization. As part of a continuing program on the synthesis of sugarand nucleoside-derived aminooxy acids, [13][14][15][16][17] we report herein the synthesis of nucleo aminooxy acid derivatives with thymine or cytosine connected to the side chain of a β-aminooxy acid through either an amide or a triazole linkage (Figure 1). To the best of our knowledge, nucleo aminooxy acids have not been previously reported in the literature.…”

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confidence: 99%

Synthesis of Nucleo Aminooxy Acid Derivatives

Noël

Xie

2012

Synthesis

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Nucleobase-functionalized peptides have attracted increasing interest because of their well-ordered secondary structures and stability toward enzymatic degradations. We have designed and synthesized nucleo aminooxy acids as novel building blocks for nucleopeptides. Four nucleo aminooxy acid derivatives with cytosine or thymine in the side chain linked by an amide or a triazole moiety have been synthesized from L-serine.Key words: nucleo aminooxy acids, nucleopeptides, N-oxy nucleopeptides, cytosine, thymine, amides, triazoles, L-serine, eliminations Nucleo amino acids are synthetic amino acids bearing nucleobases covalently linked to their side chains. Various peptides containing nucleo α-and β-amino acids have been reported as being able to form rigid and helical structures as well as well-defined double strands with complementary sequences. [1][2][3][4][5][6][7] Moreover, nucleopeptides have recently emerged as a promising alternative to peptide nucleic acids, 8,9 able to penetrate into a cell nucleus without cytotoxic effects. 10Aminooxy acids are analogues of amino acids bearing an oxyamine function (O-NH 2 ) in the place of amine. Peptides of aminooxy acids have an ease of forming welldefined structures like α-, β-and γ-turns or helices thanks to intramolecular hydrogen-bond formation. 11,12It would therefore be interesting to synthesize nucleo aminooxy acids containing nucleobases on the side chain of aminooxy acids in order to study the secondary structure and DNA/RNA binding properties of the corresponding Noxy nucleopeptides, since both the N-oxy peptide and the nucleobases could contribute to structure organization. As part of a continuing program on the synthesis of sugarand nucleoside-derived aminooxy acids, [13][14][15][16][17] we report herein the synthesis of nucleo aminooxy acid derivatives with thymine or cytosine connected to the side chain of a β-aminooxy acid through either an amide or a triazole linkage (Figure 1). To the best of our knowledge, nucleo aminooxy acids have not been previously reported in the literature. The target nucleo aminooxy acid derivatives are accessible from the β-phthalimidooxy ester 8 (Scheme 1). This compound has been previously prepared from L-serine by Burke and co-workers. 18 We have synthesized the phthalimidooxy ester 7 from L-Ser-OMe (5) by N-tritylation and Mitsunobu reactions, and purified compounds 6 and 7 by simple precipitation, without column chromatography. Treatment of 7 with 36% hydrochloric acid in dichloromethane as reported led, however, to a mixture of compounds. Removal of the trityl group was then achieved with acetyl chloride in methanol, leading to the amine salt 8 in 65% yield. Coupling of 8 with N 4 -Cbz-protected cytosin-1-ylacetic acid 9 19 using BOP reagent furnished the cytosin-1-yl-substituted aminooxy ester 2a in 53% yield; however, reaction of 8 with thymin-1-ylacetic acid (14) 20 using EDC/HOAt led to the corresponding polar thymin-1-yl-substituted aminooxy ester which proved to be difficult to purify.We then decided to rep...

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“…Moreover, the oxyamine function could be used for generating libraries of conjugates through chemoselective neoglycosylation with reducing sugars, oxime ligation with carbonyl compounds, in addition to coupling with carboxylic acids. With a continuing interest in N ‐oxyamide modified biomolecules, we reported herein a stereoselective synthesis of both (2 R )‐ and (2 S )‐aminooxy analogues of β‐ O ‐glucosylserine 1 and 2 (Scheme ) and their use for the preparation of N ‐oxyamide‐linked glycoconjugates.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of (2R)- and (2S)-aminooxy analogues of β-O-glucosylserine andN-oxyamide linked glycoconjugates

2016

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Glycosyl amino acids are constituents of glycopeptides and glycoproteins playing important roles in various cellular activities and pathogenic processes. We have stereoselectively synthesized both (2R)-and (2S)-aminooxy analogues of b-O-glucosylserine from sn-(3-b-O-glucosyl)glycerol through selective protection, Mitsunobu reaction, oxidation and Lattrell-Dax epimerization reactions. N-oxyamide linked glycopetides and glycolipids have been prepared from the b-O-glucosyl aminooxy acid derivatives. 1 H NMR and IR studies suggest the formation of an a NÀO turn structure in the glycopeptide 19.

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Synthesis of nucleoside aminooxy acids

Cited by 14 publications

References 44 publications

Synthesis of O-Amino Sugars and Nucleosides

Synthesis of O-Amino Sugars and Nucleosides

Synthesis of Nucleo Aminooxy Acid Derivatives

Synthesis of (2R)- and (2S)-aminooxy analogues of β-O-glucosylserine andN-oxyamide linked glycoconjugates

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