2004
DOI: 10.1021/cc0340729
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Improved Loading and Cleavage Methods for Solid-Phase Synthesis Using Chlorotrityl Resins:  Synthesis and Testing of a Library of 144 Discrete Chemicals as Potential Farnesyltransferase Inhibitors

Abstract: The use of chlorotrityl resins for the immobilization of amines is sometimes deterred by the lengthy process of loading the reactants on the resins and product decomposition caused by the reactive chlorotrityl group in the presence of 1% TFA as a cleavage agent. Here, we report improved methods developed for selective and efficient loading of aminobenzoic acid derivatives on chlorotrityl resins and for cleavage of aniline-containing products from the resins without decomposition. These methods led to the synth… Show more

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Cited by 14 publications
(14 citation statements)
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“…Therefore, a fluorogenic substrate for the purpose of detecting seminal fluid within a forensic casework framework was constructed through the sequential coupling of immobilized Rh-110 to amino acids HSSKLQ, a sequence previously reported by Denmeade et al 11 as a proteolytic cleavage site of seminal fluid-specific protease prostate specific antigen (PSA). Rh-110 was successfully anchored to the 2-chlorotrityl chloride resin (known to react with aromatic amines in the presence of a base such as pyridine or N,N-Diisopropylethylamine (DIPEA)) 12 in the first step towards substrate preparation.…”
Section: Please Do Not Adjust Marginsmentioning
confidence: 99%
See 1 more Smart Citation
“…Therefore, a fluorogenic substrate for the purpose of detecting seminal fluid within a forensic casework framework was constructed through the sequential coupling of immobilized Rh-110 to amino acids HSSKLQ, a sequence previously reported by Denmeade et al 11 as a proteolytic cleavage site of seminal fluid-specific protease prostate specific antigen (PSA). Rh-110 was successfully anchored to the 2-chlorotrityl chloride resin (known to react with aromatic amines in the presence of a base such as pyridine or N,N-Diisopropylethylamine (DIPEA)) 12 in the first step towards substrate preparation.…”
Section: Please Do Not Adjust Marginsmentioning
confidence: 99%
“…Rh-110 was successfully anchored to the 2-chlorotrityl chloride resin (known to react with aromatic amines in the presence of a base such as pyridine or N,N-diisopropylethylamine (DIPEA)) 12 in the first step towards substrate preparation. Upon reaction, the resin exhibited a deep red coloration that was retained after extensive washing, indicating successful dye incorporation.…”
mentioning
confidence: 99%
“…The most critical feature of solid-phase synthesis is the attachment of substrate to the polymeric resin (Scott, 2009), so the first anchoring unit should be loaded efficiently with polystyrene support and the linkage should be stable enough to tolerate the subsequent chemical transformations and chemical environment. Trityl linker is commonly used in solidphase peptide synthesis which allows the "protected" compound to be subjected to various chemical manipulations and consequently to afford pure compounds without numerous purification steps (Park et al, 2004;Olsen et al, 2004;Lundquist et al, 2006;Crestey et al, 2008). Additionally, the trityl linker is readily cleaved under mild acidic condition (1% TFA in dichloromethane) owing to the high stability of trityl cations (Rothman et al, 2003).…”
Section: Introductionmentioning
confidence: 99%
“…11 In our search for an alternative class of compounds that could inhibit PGGT-1, we noted that (1) the action of PGGT-1 is highly reminiscent of that of PFT 7 and (2) effective ambiphilic peptidic PFT inhibitors, having a polar head, that are assembled from simple building blocks connected through amide bonds have been reported. 12 These observations led us to design a combinatorial strategy aimed at the generation of ambiphilic oligopeptides as potential PGGT-1 inhibitors, 13 based on the use of commercially available building blocks. Our strategy, which further includes a random optimization item, 14 can be summarized as follows (Schemes 1 and 2).…”
mentioning
confidence: 99%