Emollient, humectant, and fluorescent α,β-unsaturated thiol esters for long-acting skin applications

Robinson, Carmen; Hartman, Rosemarie F.; Rose, Seth D.

doi:10.1016/j.bioorg.2008.06.004

Cited by 10 publications

(10 citation statements)

References 11 publications

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“…The reaction was allowed to stir at room temperature for 3 h, was concentrated, and the product was purified on silica gel, eluting with 97∶2∶1 DCM/Hexanes/TEA to furnish 10 (51.4 mg, 30%) as a yellow film. Characterization data matched with literature [97].…”

Section: Methodssupporting

confidence: 57%

Synthesis of Non-linear Protein Dimers through a Genetically Encoded Thiol-ene Reaction

et al. 2014

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Site-specific incorporation of bioorthogonal unnatural amino acids into proteins provides a useful tool for the installation of specific functionalities that will allow for the labeling of proteins with virtually any probe. We demonstrate the genetic encoding of a set of alkene lysines using the orthogonal PylRS/PylTCUA pair in Escherichia coli. The installed double bond functionality was then applied in a photoinitiated thiol-ene reaction of the protein with a fluorescent thiol-bearing probe, as well as a cysteine residue of a second protein, showing the applicability of this approach in the formation of heterogeneous non-linear fused proteins.

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Section: Methodssupporting

confidence: 57%

Synthesis of Non-linear Protein Dimers through a Genetically Encoded Thiol-ene Reaction

et al. 2014

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“…Furthermore the sulphonamides are the best-known inhibitors of the carbonic anhydrase enzyme, currently used for the treatment of glaucoma in clinical medicine [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 5-amino-1,3,4-thiadiazole-2-sulphonamide derivatives and their inhibition effects on human carbonic anhydrase isozymes

Kasımoğulları

Bülbül

Mert

et al. 2010

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…This thiol is not commerciallya vailable and was prepared by following a reported procedure. [12] Interestingly,a ll S-Michaelr eactions proceeded with complete diastereoselectivity,a so nly au nique diastereoisomerw as observedi nt he reaction mixture. Therefore, the resultsr eported herein indicate ar obust stereoinduction mechanism for the protonation of the enolate adduct upon conjugate addition.…”

Section: Resultsmentioning

confidence: 94%

Cell‐Penetrating Peptides Containing Fluorescent d‐Cysteines

Navo

Asín

Gómez-Orte

et al. 2018

Chemistry A European J

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A series of fluorescent d-cysteines (Cys) has been synthesized and their optical properties were studied. The key synthetic step is the highly diastereoselective 1,4-conjugate addition of aryl thiols to a chiral bicyclic dehydroalanine recently developed by our group. This reaction is fast at room temperature and proceeds with total chemo- and stereoselectivity. The Michael adducts were easily transformed into the corresponding amino acids to study their optical properties and, in some selected cases, into the corresponding N-Fmoc-d-cysteine derivatives to be used in solid-phase peptide synthesis (SPPS). To further demonstrate the utility of these non-natural Cys-derived fluorescent amino acids, the coumaryl and dansyl derivatives were incorporated into cell-penetrating peptide sequences through standard SPPS and their optical properties were studied in different cell lines. The internalization of these fluorescent peptides was monitored by fluorescence microscopy.

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Emollient, humectant, and fluorescent α,β-unsaturated thiol esters for long-acting skin applications

Cited by 10 publications

References 11 publications

Synthesis of Non-linear Protein Dimers through a Genetically Encoded Thiol-ene Reaction

Synthesis of Non-linear Protein Dimers through a Genetically Encoded Thiol-ene Reaction

Synthesis of 5-amino-1,3,4-thiadiazole-2-sulphonamide derivatives and their inhibition effects on human carbonic anhydrase isozymes

Cell‐Penetrating Peptides Containing Fluorescent d‐Cysteines

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