Synthesis and transmembrane transport studies by NMR of a glucosyl phospholipid of thymidine

Neumann, Jean‐Michel; Debouzy, Jean‐Claude; Iglesias‐Guerra, Fernando; Gouyette, Catherine; Dupraz, B.; Tam, Huynh Dinh

doi:10.1021/ja00194a018

Cited by 37 publications

(10 citation statements)

References 5 publications

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“…Alkaline deprotection afforded the glucosyl phosphodiester 10 (sodium salt). Subsequent conversion to its tetrabutylammonium salt by a Dowex 50 WX2 exchange resin [( n -C 4 H 9 )N + form], followed by alkylation with the acetylated iodoethyl thioglucoside 6 gave the desired phosphotriester derivative 3 . Alternatively, by DBU treatment the β-cyanoethyl group of phosphotriester 8 was removed selectively to yield the peracetylated phosphodiester 9 , which was used as reference sample in the stability studies.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Studies of Mononucleoside Glucosyl Phosphotriester Derivatives

et al. 1997

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The synthesis and stability studies in several aqueous media of mononucleoside glucosyl phosphotriester derivatives of 3'-azido-3'-deoxythymidine are reported herein. Such neutral mononucleotides, which incorporate beta-glucopyranosidyl moieties associated to a thioethyl linker as phosphate protecting groups were designed to act as "pronucleotides", giving rise to the corresponding 5'-mononucleotide through a glucosidase-mediated activation mechanism.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Studies of Mononucleoside Glucosyl Phosphotriester Derivatives

et al. 1997

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“…Thymidine 5 0 -alkylphosphates (5, 6) were synthesised according to the method of Neumann et al (1989) with a slight modification, as follows. A mixture of TMP tetrabutylammonium (300 mmol) and lauryl bromide or hexadecyl bromide (3 mmol) in dimethylacetamide (2 mL) was heated at 80 C for 16 h. The resulting mixture was appropriately diluted with CH 2 Cl 2 and the alkylated product was purified by silica gel column chromatography eluting with CH 2 Cl 2 -methanol.…”

Section: Syntheses Of Nucleotide Derivativesmentioning

confidence: 99%

Selective inhibition of embryonic development in starfish by long-chain alkyl derivatives of UMP, TMP and AMP

Tanaka¹,

Ogita²,

Usuki

et al. 2009

Natural Product Research

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Nucleoside analogs have been evaluated as useful tools for the investigation of the mechanism of cell differentiation. We thus examined the effects of nucleoside 5'-alkylphosphates (1-10) on the morphogenetic development of starfish embryos. These nucleotide derivatives were all permissive for their development up to the blastula stage, but the derivatives with lauryl side chain selectively inhibited one of the following stages into bipinnaria larvae. Among them, uridine 5'-laurylphosphate (2) inhibited gastrulation of the blastula, as is the case with the antibiotic tunicamycin, suggesting its inhibitory activity on sulfated and non-sulfated glycoprotein syntheses. Unexpectedly, adenosine 5'-laurylphosphate (8) was evaluated as a novel class of inhibitor that can arrest the embryos exactly at the late gastrula stage, absolutely inhibiting cell differentiation involved in the development of gastrointestinal tract. This is the first report on the appearance of biological activity due to the structural modification of a naturally-occurring molecule, which is critical to the morphogenetic development of multicellular organisms.

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“…In 1989/1990, Huynh-Dinh and co-workers [46] published the synthesis of 6-dglucopyranosyl hexadecyl 5'-thymidinylphosphate (85) as a model compound for the biochemically important dolicyl glucose-1-phosphate (Scheme 12). The target nucleolipid of the authors was a phosphotriester composed from thymidine, glucose-6phosphate, and hexadecan-1-ol.…”

Section: Fig 2 Liposidomycinsmentioning

confidence: 99%

Nucleolipids: Natural Occurrence, Synthesis, Molecular Recognition, and Supramolecular Assemblies as Potential Precursors of Life and Bioorganic Materials

Rosemeyer

2005

C&B

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Nucleolipids are hybrid molecules composed of a nucleobase, a nucleoside, a nucleotide or an oligonucleotide (either DNA or RNA), and a lipophilic moiety, which might be either simply a single- or double-chained alkyl (or alkenyl) moiety or a carbocyclic hydrocarbon such as cholesterol, a vitamin, or a bile acid. This review covers all aspects of nucleolipids, namely their natural occurrence, their synthesis, their molecular recognition, as well as aggregation behavior, either in aqueous or non-aqueous solution. Potential future aspects of nucleolipids in material sciences and for the elucidation of biochemical reactions in living cells are discussed.

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Synthesis and transmembrane transport studies by NMR of a glucosyl phospholipid of thymidine

Cited by 37 publications

References 5 publications

Synthesis and Studies of Mononucleoside Glucosyl Phosphotriester Derivatives

Synthesis and Studies of Mononucleoside Glucosyl Phosphotriester Derivatives

Selective inhibition of embryonic development in starfish by long-chain alkyl derivatives of UMP, TMP and AMP

Nucleolipids: Natural Occurrence, Synthesis, Molecular Recognition, and Supramolecular Assemblies as Potential Precursors of Life and Bioorganic Materials

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