Diazotization of <i>S</i>-Sulfonyl-cysteines

Mear, Sarah Jane; Jamison, Timothy F.

doi:10.1021/acs.joc.9b02630

Cited by 8 publications

(5 citation statements)

References 32 publications

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“…DoE has been used extensively in the optimization of chemical processes, particularly in pharmaceutical and fine chemical settings. DoE is often used for studies relating to enhancing the yield − and purity − of particular products but is also used for drug formulations − and delivery, − analytical method development, − and more. − This is because there are numerous and undisputed benefits to the use of DoE for experimental parameter screening and optimization, especially when compared with traditional human intuition-guided experimentation. With the rise of user-friendly software packages and the increased awareness of the chemical community, there has been a large uptake of this statistical method in recent years, although the technique itself has been around since the mid-20th century .…”

Section: Design Of Experiments (Doe)mentioning

confidence: 99%

A Brief Introduction to Chemical Reaction Optimization

et al. 2023

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From the start of a synthetic chemist’s training, experiments are conducted based on recipes from textbooks and manuscripts that achieve clean reaction outcomes, allowing the scientist to develop practical skills and some chemical intuition. This procedure is often kept long into a researcher’s career, as new recipes are developed based on similar reaction protocols, and intuition-guided deviations are conducted through learning from failed experiments. However, when attempting to understand chemical systems of interest, it has been shown that model-based, algorithm-based, and miniaturized high-throughput techniques outperform human chemical intuition and achieve reaction optimization in a much more time- and material-efficient manner; this is covered in detail in this paper. As many synthetic chemists are not exposed to these techniques in undergraduate teaching, this leads to a disproportionate number of scientists that wish to optimize their reactions but are unable to use these methodologies or are simply unaware of their existence. This review highlights the basics, and the cutting-edge, of modern chemical reaction optimization as well as its relation to process scale-up and can thereby serve as a reference for inspired scientists for each of these techniques, detailing several of their respective applications.

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Section: Design Of Experiments (Doe)mentioning

confidence: 99%

A Brief Introduction to Chemical Reaction Optimization

et al. 2023

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“…The sulfonyl group is first introduced to the Cys residue, and diazotisation is subsequently used to generate the a-hydroxy or a-chloro acid (depending on whether H 2 SO 4 or HCl is used). 260 5.10.6 3-Nitro-2-pyridinesulfenyl (Npys). The 3-nitro-2pyridinesulfenyl (Npys) 261 protecting group (Fig.…”

Section: Benzyloxymethyl (Bom)mentioning

confidence: 99%

Cysteine protecting groups: applications in peptide and protein science

2021

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“…3a) 20 minutes after the beginning of the experiment can be explained by the fact that in the presence of the primary amino acids in acidic media (in our experiment the pH of the initial CYS solution is 5.20, and the pH of the immediate mixed CS-1 and CS-2 solutions is 3.30 and 3.45 respectively) the NO 2 À (more precisely HNO 2 , which in an acidic media forms an extremely reactive NO + ) can react via the general scheme (the diazotization reaction): R-NH 3 + + NO 2 À = R-OH + N 2 + H 2 O. 46,47 Since the activity of the aliphatic amino-group is higher than that of the aromatic the former is not diazotized at pH o 3. 48 Furthermore, the reaction between CYS and AgNO 2 was accompanied by the formation of gas bubbles.…”

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confidence: 99%