Syntheses of Functionalized Biotin N-1‘ Derivatives:  New Tools for the Control of Gene Expression with Small Molecules

Inard, Cyril; Fourcade, Emmanuelle; Baron, Rudi; Tovar, Daniel; Chaisemartin, L. De; Blonski, Casimir; Faye, Jean-Charles

doi:10.1021/bc060010a

Cited by 6 publications

(7 citation statements)

References 10 publications

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“…Trimer 3 was N-Boc deprotected with TFA and evaporated to produce the crude TFA salt that was subsequently extended by D-Biotin through EDC-HCl mediated coupling to form the biotinylated trimer linker 4 scaffold in 80% yield. Inard et al 16 demonstrated that sulfur containing biotin derivatives were inert towards palladium, and thus palladium-mediated hydrogenation of benzyl ester 4 liberated the free carboxylic acid of the biotinylated linker 5 in 84% yield. Biotinylated linker 5 was equipped for direct esterification with the appropriate bioactive molecule, such as lagunamide A.…”

Section: Resultsmentioning

confidence: 99%

A pre-biotinylated linker assembly for single-step preparation of novel biosensors

Banasik¹

2017

Org. Commun.

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A simple and efficient method for the synthesis of biotin pre-functionalized linkers via orthogonal protecting group elongation strategy is reported for a single-step preparation of new biosensor probes. The target compound 4-(4-(4-(5-((3S, 4S, 6R)-2-oxohexahydro-1H-thieno[3,4]imidazol-4-yl) pentanamido) butanamido)butanamido) butanoic acid (5) was synthesized in five linear steps with a 40% overall yield.

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Section: Resultsmentioning

confidence: 99%

A pre-biotinylated linker assembly for single-step preparation of novel biosensors

Banasik¹

2017

Org. Commun.

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“…Increasing concentrations of NaCl were used to elute the labeled scFv, which was obtained at NaCl concentrations of 400 to 600 mM (Figure 3). We have shown that N′1 modifications of D-biotin result in a major loss of affinity for avidin (35). We made use of this property in the purification of labeled scFv on streptavidin, by adding biotin to the elution buffer.…”

Section: Discussionmentioning

confidence: 99%

“…It was essential for this labeling to be selective and to have no effect on antigen-scFv recognition. On the basis of previous work on the synthesis of functionalized biotin N-1′ derivatives (35), we synthesized a biotin N-1′ fluorescein derivative carrying a thiol inducer of intein splicing on its valeric chain. This molecule double-labeled the scFv, its biotin moiety facilitating purification of the labeled protein and its fluorescein moiety opening up opportunities for the use of fluorescence-based technology.…”

Section: Discussionmentioning

confidence: 99%

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Synthesis and Application of a N-1′ Fluorescent Biotinyl Derivative Inducing the Specific Carboxy-Terminal Dual Labeling of a Novel RhoB-Selective scFv

et al. 2009

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The fluorescent site-specific labeling of protein would provide a new, easy-to-use alternative to biochemical and immunochemical methods. We used an intein-mediated strategy for covalent labeling of the carboxy-terminal amino acid of a RhoB-selective scFv previously isolated from a phage display library (a human synthetic V(H) + V(L) scFv phage library). The scFv fused to the Mxe intein was produced in E. coli and purified and was then labeled with a newly synthesized fluorescent biotinyl cysteine derivative capable of inducing scFv-Mxe intein splicing. In this study, we investigated the splicing and labeling properties of various amino acids in the hinge domain between scFv and Mxe under thiol activation. In this dual labeling system, the fluorescein is used for antibody detection and biotin is used for purification, resulting in a high specific activity for fluorescence. We then checked that the purified biotinylated fluorescent scFv retained its selectivity for RhoB without modification of its affinity.

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“…59 However, when compound 133 was allowed to react with CSA, ether 134 again was obtained as the major product as indicated by TLC. 120 When this mixture proved difficult to separate, the mixture was treated with TsOH in MeOH in hopes that the two compounds could be separated following deprotection of the MOM-acetal. However, this also produced an inseparable mixture of the two products.…”

Section: Figure 40 Attempted Alkylation Of Benzyl Alcohol 104mentioning

confidence: 99%

Cascade cyclizations in total synthesis

Ulrich¹

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Plant-derived natural products continue to be a valuable source of useful therapies for cancer as well as other diseases. As part of a continuing mission to obtain anticancer agents from natural sources, researchers at the National Cancer Institute (NCI) established the 60 human tumor cell line anticancer screen. The schweinfurthins are one family of unique natural products discovered through this screening process, and most of the schweinfurthins exhibit potent and differential activity in the 60-cell line screen. Importantly, the pattern of activity displayed by the schweinfurthins shows no correlation to any clinically used anticancer drug, indicating that this family of natural products probably acts via a novel mechanism or at a novel target. Our group has conducted extensive structure-activity relationship studies in an effort to illuminate the mechanism of action of the schweinfurthins. In this thesis, the preparation and biological activity of a number of new schweinfurthin F analogues possessing variations in the D-ring alkyl chain and stilbene moiety will be discussed. These studies have clarified the importance of the D-ring substituent to the schweinfurthins' pharmacophore. Based on the results obtained from the exploration of the structural requirements of these natural products, it was determined that the right-half of the schweinfurthins would be an appropriate site for attachment of a molecular probe to be used in affinity experiments. The synthesis of these biotinylated probes will be presented in detail, and their use in pull-down assays will be summarized. The preparation of key schweinfurthin intermediates has involved the extensive use of Lewis acid-mediated cationic cascade cyclizations terminated by methoxymethyl (MOM)-protected phenols. Those successes have inspired investigations of additional applications of these cyclizations. In particular, a variant of these cyclizations using "MOM-protected" enol ethers as reasonable substitutes for β-keto ester terminating moieties has been studied. These interrelated studies involving the synthesis of vi TABLE OF CONTENTS LIST OF TABLES.

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Syntheses of Functionalized Biotin N-1‘ Derivatives: New Tools for the Control of Gene Expression with Small Molecules

Cited by 6 publications

References 10 publications

A pre-biotinylated linker assembly for single-step preparation of novel biosensors

A pre-biotinylated linker assembly for single-step preparation of novel biosensors

Synthesis and Application of a N-1′ Fluorescent Biotinyl Derivative Inducing the Specific Carboxy-Terminal Dual Labeling of a Novel RhoB-Selective scFv

Cascade cyclizations in total synthesis

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