N-Substituted arylsulfonamide building blocks as alternative submonomers for peptoid synthesis

Vézina‐Dawod, Simon; Derson, Antoine; Biron, Éric

doi:10.1016/j.tetlet.2014.11.104

Cited by 14 publications

(16 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…N-Protection of commercially available amino alcohols 1a-f was performed with 2-Nos-Cl under standard conditions followed by O-tert-butylation of compounds 2a-f with magnesium perchlorate and di-tert-butylcarbonate in refluxing dichloromethane ( Figure 1) [7]. A first study was performed with the submonomer N-(2-methoxyethyl)-2-nitrobenzenesulfonamide on a supported bromoacetylated Phe to identify the optimal conditions for bromine displacement with the N-substituted arylsulfonamide derivatives [7]. Different reaction parameters were tested and after the nucleophilic displacement and cleavage from the Rink amide resin, the conversion rate was evaluated by HPLC.…”

Section: Resultsmentioning

confidence: 99%

N-Substituted Arylsulfonamides as Alternative Building Blocks in Peptoid and Peptide Synthesis

Vézina‐Dawod¹,

Jobin²,

Derson³

et al. 2015

Peptides 2015, Proceedings of the 24th American Peptide Symposium

Self Cite

View full text Add to dashboard Cite

Section: Resultsmentioning

confidence: 99%

N-Substituted Arylsulfonamides as Alternative Building Blocks in Peptoid and Peptide Synthesis

Vézina‐Dawod¹,

Jobin²,

Derson³

et al. 2015

Peptides 2015, Proceedings of the 24th American Peptide Symposium

Self Cite

View full text Add to dashboard Cite

“…At this point, the question arose about the utility of the Rh 2 -method in such a case. ECD in situ spectra of 6 with Rh 2 (O 2 CCH 3 ) 4 were and #1 of quinidine (4) and its structures (bottom) calculated at B3LYP-D3/aug-cc-pVDZ/PCM/CHCl 3 level; frequencies scaled by a factor 0.984 for 3 and 0.980 for 4; band-width σ = 10 cm −1 measured both in CH 3 CN and EtOH. They exhibit a similar shape, although in EtOH CE at~295 nm splits to two not fully resolved maxima (Figure 8).…”

Section: Oseltamivir (6)mentioning

confidence: 99%

“…Many of their applications consist of their use as ligands in asymmetric synthesis to afford small heterocyclic derivatives as, for example, pyrrolidine, morpholinones, 2 or transoxazolines. 3 The chiral amino alcohols are also widely used in peptoid synthesis, 4 and click chemistry to obtain functionalized triazoles. 5 As a consequence of significant biological activity and broad applicability in organic synthesis, vic-amino alcohols are an important class of organic compounds, whose absolute configuration (AC) determination is vital.…”

Section: Introductionmentioning

confidence: 99%

“…ECD spectra of quinine(3) and quinidine(4) recorded in CHCl 3 (bottom) and their ECD spectra in the presence of Rh 2 (O 2 CCH 3 ) 4 (top) measured 24 h after dissolution in CHCl 3 with schematic representation of correlation rule for 580 nm band on the example of 3 in the insert (R in rule projection = quinoline ring) FIGURE 4 VCD (top) and IR (bottom) spectra of quinine (3) recorded in CDCl 3 compared with calculation at B3LYP-D3/augcc-pVDZ/PCM/CHCl 3 level of theory; frequencies scaled by a factor 0.984; band-width σ = 10 cm −1…”

mentioning

confidence: 99%

See 1 more Smart Citation

Chirality sensing of bioactive compounds with amino alcohol unit via circular dichroism

2017

View full text Add to dashboard Cite

The aim of the present work was to test various chiroptical techniques, including in particular the in situ dirhodium methodology, to assign the absolute configuration of 1,2- and 1,3-amino alcohols. As models, we selected mainly compounds that have both an additional strongly absorbing and interfering chromophoric system and application in medicinal chemistry. Determination of the absolute configuration (AC) of the tested molecules such as cinchona alkaloids, Tamiflu, and others was carried out using a combination of electronic and vibrational circular dichroism (ECD, VCD) spectroscopy. It has been demonstrated that both 1,2- and 1,3-aminol moieties are subject to the same sector rule correlating stereostructure of formed Rh -complex with chiroptical properties, and that the changes in the position of the stereogenic center do not affect its proper use.

show abstract

“…As mentioned above the conditions required for deprotection must be mild enough to avoid dehydration of the hydroxylated product, therefore strongly acidic conditions should be avoided. Considering the two issues of ease of deprotection and versatility with respect to carboxylate incorporation, nitrophenylsulfonamides (Nosyl) groups are of interesta st hey can be removed under mildly basic conditions with at hiolatev ia a nucleophilic aromatic substitution (see Figure 4), [27] and also offers four different sites for introduction of ac arboxylate moiety.…”

Section: Introductionmentioning

confidence: 99%

Enzymatic Late‐Stage Oxidation of Lead Compounds with Solubilizing Biomimetic Docking/Protecting groups

Vickers

Backfisch

Oellien

et al. 2018

Chemistry A European J

View full text Add to dashboard Cite

Late‐stage functionalization of lead compounds is of high interest in drug discovery since it offers an easy access to metabolites and derivatives of a lead compound without the need to redesign an often long multistep synthesis. Owing to their high degree of chemoselectivity, biocatalytic transformations, enzymatic oxidations in particular, are potentially very powerful because they could allow the synthesis of less lipophilic derivatives of a lead compound. In the majority of cases, enzymatic oxidations have been used in an empirical way as their regioselectivity is difficult to predict. In this publication, the concept of using docking/protecting groups in a biomimetic fashion was investigated, which could help steer the regioselectivity of a P450BM3‐mediated oxidation. A novel set of docking/protecting groups was designed that can be cleaved under very mild conditions and address the often problematic aqueous solubility of the substrates. Vabicaserin was used as tool compound containing typical groups such as basic, aliphatic, and aromatic moieties. The results were rationalized with the help of in silico docking and molecular dynamic studies.

show abstract

N-Substituted arylsulfonamide building blocks as alternative submonomers for peptoid synthesis

Cited by 14 publications

References 42 publications

N-Substituted Arylsulfonamides as Alternative Building Blocks in Peptoid and Peptide Synthesis

N-Substituted Arylsulfonamides as Alternative Building Blocks in Peptoid and Peptide Synthesis

Chirality sensing of bioactive compounds with amino alcohol unit via circular dichroism

Enzymatic Late‐Stage Oxidation of Lead Compounds with Solubilizing Biomimetic Docking/Protecting groups

Contact Info

Product

Resources

About