A Novel Sensitive Colorimetric Assay for Visual Detection of Solid-Phase Bound Amines

Madder, Annemieke; Farcy, Nadia; Hosten, N.; Muynck, Hilde De; Clercq, Pierre J. De; Barry, John G.; Davis, Anthony P.

doi:10.1002/(sici)1099-0690(199911)1999:11<2787::aid-ejoc2787>3.0.co;2-d

Cited by 69 publications

(13 citation statements)

References 20 publications

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“…The de Clercq group, in particular, has followed a similar course for the identification of peptides that accelerate serine O-acylation, though a mention of reversible histidine N-acylation is made. [7][8][9] The focus of our efforts was on peptide secondary structures that maximized our ability to convert peptide hit sequences into active site structures that reliably position critical side-chains into 3-dimensional space. Short peptides that take on helical structure in organic solvent (α-helix and/or 3 10 -helix) were selected as the scaffold because the variable i + 3/i − 3 and i + 4/i − 4 positions in the linear sequence place functionality in close proximity to the i-position, to which a histidine (His) residue was placed (Fig.…”

Section: Introductionmentioning

confidence: 99%

Identification and optimization of short helical peptides with novel reactive functionality as catalysts for acyl transfer by reactive tagging

et al. 2014

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Herein we describe the screening and subsequent optimization of peptide catalysts for ester activation. A combinatorial methodology using dye-tagged substrate analogs is described for determining which components of a His-containing helical library display acyl transfer activity. We found that helical peptides display high activity, and amino acids that reinforce this propensity are advantaged. Through this approach two new structural motifs have been discovered that are capable of activating esters in organic solvents. Unlike most acyl transfer catalysts functioning in organic solvents, these catalysts are histidine- rather than N-alkyl histidine-based. Longer peptides with localization of reactive groups on the C-terminal end of the peptide were found to further enhance catalytic activity up to ∼2800-fold over background.

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Section: Introductionmentioning

confidence: 99%

Identification and optimization of short helical peptides with novel reactive functionality as catalysts for acyl transfer by reactive tagging

et al. 2014

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“…4-Fold molar excess of each amino acid and a coupling reagent TBTU (N,N,N 0 ,N 0 -tetramethyl-O-(benzotriazol-1-yl)uronium tetrafluoroborate) were used. The efficiency of each coupling/deprotection reaction was determined by NF31 39 with standard coupling reagents. After 2 min of preactivation, the mixture was added to the resin and irradiated in a microwave reactor three times in 5 min cycles with 15 min intervals when it cools down to ambient temperature.…”

Section: General Procedures For Synthesis Of Tetramers 10e13mentioning

confidence: 96%

Oligomers and peptidomimetics consisting of methyl 3-amino-2,3-dideoxyhexopyranosiduronic acids

et al. 2015

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“…with intermittent manual stirring for 90 min. Subsequent couplings were checked by the De Clercq test [58]. Fmoc deprotection was carried out by two treatments of 10 min with piperidine/DMF (2 : 8, v/v) and two extra treatments of 5 min with piperidine/DBU/toluene/DMF (5 : 5 : 20 : 70, v/v).…”

Section: (B) Avp 1-9: H-cys-tyr-phe-gln-asn-cys-pro-lys-gly-nhmentioning

confidence: 99%

Evolutionary combinatorial chemistry, a novel tool for SAR studies on peptide transport across the blood-brain barrier. Part 2. Design, synthesis and evaluation of a first generation of peptides

et al. 2005

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The use of high-throughput methods in drug discovery allows the generation and testing of a large number of compounds, but at the price of providing redundant information. Evolutionary combinatorial chemistry combines the selection and synthesis of biologically active compounds with artificial intelligence optimization methods, such as genetic algorithms (GA). Drug candidates for the treatment of central nervous system (CNS) disorders must overcome the blood-brain barrier (BBB). This paper reports a new genetic algorithm that searches for the optimal physicochemical properties for peptide transport across the blood-brain barrier. A first generation of peptides has been generated and synthesized. Due to the high content of N-methyl amino acids present in most of these peptides, their syntheses were especially challenging due to over-incorporations, deletions and DKP formations. Distinct fragmentation patterns during peptide cleavage have been identified. The first generation of peptides has been studied by evaluation techniques such as immobilized artificial membrane chromatography (IAMC), a cell-based assay, log Poctanol/water calculations, etc. Finally, a second generation has been proposed.

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A Novel Sensitive Colorimetric Assay for Visual Detection of Solid-Phase Bound Amines

Cited by 69 publications

References 20 publications

Identification and optimization of short helical peptides with novel reactive functionality as catalysts for acyl transfer by reactive tagging

Identification and optimization of short helical peptides with novel reactive functionality as catalysts for acyl transfer by reactive tagging

Oligomers and peptidomimetics consisting of methyl 3-amino-2,3-dideoxyhexopyranosiduronic acids

Evolutionary combinatorial chemistry, a novel tool for SAR studies on peptide transport across the blood-brain barrier. Part 2. Design, synthesis and evaluation of a first generation of peptides

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