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项与 Lipitek International, Inc. 相关的文献（医药）

1999-11-01·Chemistry and Physics of Lipids3区 · 生物学

New approaches to synthesis of stereospecific sphingomyelin

3区 · 生物学

Review

作者: Weis, A L

Enormous progress in the asymmetric synthesis of stereochemically and chemically pure D-erythro-sphingosine and ceramides led to the development of a practical, efficient, easily scaleable process to provide industrial quantities of chiral sphingosine and ceramides. This established a new platform of chiral starting materials which facilitate the synthesis of complex sphingolipids. Utilizing stereochemically homogeneous, fully synthetic ceramides, two efficient synthetic methods were developed for the preparation of ultra pure stereochemically homogeneous sphingomyelins. The first method adapted highly efficient phosphoramidite technology from oligonucleotide chemistry. This method allows selective insertion of a phosphocholine moiety into 3-O-protected ceramide through phosphitylation, followed by choline attachment, phosphite oxidation and deprotection. This route provides stereochemically homogeneous sphingomyelin in 35-79% yield. The second route is based on the reaction of selectively protected ceramides with cyclic chlorophosphate followed by treatment with trimethylamine to give the desired sphingomyelins in 50% yield. Multigram quantities of 14C-labeled N-palmitoyl-D-erythro-sphingomyelin were produced with specific activity > 1000 dpm/nmol.

Synthesis of dendritic sterically hindered fluorophores: A novel series of amplified fluorescent probes.

作者: Alferiev, Ivan S. ; Martin, Vladimir V. ; Weis, Alexander L.

In the detection and quantification of mol. probes, particularly in FISH diagnostics, mutual fluorescence quenching of aromatic fluorophores is considered a major drawback of amplified mol. probes employing multiple fluorophore moieties.To overcome this problem and to amplify the fluorescent signal, a novel series of fluorescein conjugates with adamantane 1,3,5,7-tetracarboxylic acid was synthesized.Evaluation of the fluorescent properties of these conjugates established the advantages of a rigid adamantane rigid core.The quantum yields of fluorescence for adamantane conjugates were significantly higher than for analogs with flexible spacers and the same number of fluorescein residues.The novel fluorescent adamantane conjugates were employed in the preparation of functional derivatives and nucleic acid probes.Synthesis, fluorescent properties and potential applications of the amplified fluorescent probes will be presented.

Synthesis of novel nitroxide radicals containing fluorescent moieties: Fluorophores with an internal redox trigger.

作者: Martin, Vladimir V. ; Berezina, Tatyana A. ; Weis, Alexander L. ; Likhtenshtein, Gertz I. ; Lozinsky, Evgenia

The combination in the same mol. of a fluorophore and a nitroxide free radical center yields a non-fluorescent compound due to a strong exchange interaction between them.Altering the paramagnetic nature of the radical center by reduction or recombination with active free radical results in appearance of fluorescence.This phenomenon makes nitroxide-fluorophore hybrid mols. useful for biol. research or for medical diagnostics.To better understand the structural requirements for a fluorescent response and to achieve variability of triggering potentials and fluorescent properties, synthetic approaches to incorporate nitroxide moities with different redox potential and varioust fluorophores have been developed.Several series of hybrid mols. were synthesized and tested for potential diagnostic use.Synthesis of hybrid mols. and their fluorescent properties will be discussed.

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100 项与 Lipitek International, Inc. 相关的转化医学

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