Fluoride ion-catalyzed conjugate addition for easy synthesis of 3-sulfanylpropionic acid from thiol and α,β-unsaturated carboxylic acid

Gao, Shijay; Tseng, C.-C.; Tsai, Cheng Hsuan; Yao, Ching Fa

doi:10.1016/j.tet.2007.11.064

Cited by 22 publications

(13 citation statements)

References 44 publications

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“…179 At biologically relevant pH, carboxylic acids exist primarily as carboxylates, which deactivates them for Michael addition. This was observed for α,β-unsaturated ketone 259 , where α-substitution with a carboxylic acid was more deactivating than electron donating substituents like a methyl group 257 or a methoxyphenyl group 256 (Table 6).…”

Section: Other αβ-Unsaturated Carbonylsmentioning

confidence: 99%

Covalent Modifiers: A Chemical Perspective on the Reactivity of α,β-Unsaturated Carbonyls with Thiols via Hetero-Michael Addition Reactions

et al. 2016

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Although Michael acceptors display a potent and broad spectrum of bioactivity, they have largely been ignored in drug discovery because of their presumed indiscriminate reactivity. As such, a dearth of information exists relevant to the thiol reactivity of natural products and their analogs possessing this moiety. In the midst of recently approved acrylamide-containing drugs, it is clear that a good understanding of the hetero-Michael addition reaction and the relative reactivities of biological thiols with Michael acceptors under physiological conditions is needed for the design and use of these compounds as biological tools and potential therapeutics. This perspective provides information that will contribute to this understanding, such as kinetics of thiol addition reactions, bioactivities, as well as steric and electronic factors that influence the electrophilicity and reversibility of Michael acceptors. This perspective is focused on α,β-unsaturated carbonyls given their preponderance in bioactive natural products.

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Section: Other αβ-Unsaturated Carbonylsmentioning

confidence: 99%

Covalent Modifiers: A Chemical Perspective on the Reactivity of α,β-Unsaturated Carbonyls with Thiols via Hetero-Michael Addition Reactions

et al. 2016

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“…A decarboxylative Mannich addition led to the desired acrylic acid 29 . 25 Thiophenol 15 and acrylic acid 29 were combined using the TBAF·3H 2 O catalyzed reaction 22 to produce the diacid, and further elaboration to the di-NHS ester was carried out using the NHS•TFA reagent. Careful oxidation with m -CPBA produced the sulfoxide 9 .…”

Section: Resultsmentioning

confidence: 99%

Design of CID-cleavable protein cross-linkers: identical mass modifications for simpler sequence analysis

et al. 2015

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The cross-linking Mass Spectrometry (XL-MS) technique has enormous potential for studying the interactions between proteins, and it can provide detailed structural information about the interaction interfaces in large protein complexes. Such information has been difficult to obtain by conventional structural methods. One of the primary impediments to the wider use of the XL-MS technique is the extreme challenge in sequencing cross-linked peptides because of their complex fragmentation patterns in MS. A recent innovation is the development of MS-cleavable cross-linkers, which allows direct sequencing of component peptides for facile identification. Sulfoxides are an intriguing class of thermally-cleavable compounds that have been shown to fragment selectively during low-energy collisional induced dissociation (CID) analysis. Current CID-cleavable cross-linkers create fragmentation patterns in MS2 of multiple peaks for each cross-linked peptide. Reducing the complexity of the fragmentation pattern in MS2 facilitates subsequent MS3 sequencing of the cross-linked peptides. The first authentic identical mass linker (IML) has now been designed, prepared, and evaluated. Multistage tandem mass spectrometry (MSn) analysis has demonstrated that the IML cross-linked peptides indeed yield one peak per peptide constituent in MS2 as predicted, thus allowing effective and sensitive MS3 analysis for unambiguous identification. Selective fragmentation for IML cross-linked peptides from the 19S proteasome complex was observed, providing a proof-of-concept demonstration for XL-MS studies on protein complexes.

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“…18,19 Furthermore, despite our report of an early quantitative wasteless procedure for stoichiometric melt reactions without catalyst, 1 further two-step procedures have been tried to decrease the temperature by use of a catalyst at the expense of lower yield and the need for chromatographic workup. [20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37] This is also true for the later tried MCRs for the preparation of 4H-chromenes. The catalytic processes for the one-pot synthesis of 2-amino-4-aryl-3-cyano-substituted 4Hchromenes have been recently complemented by the application of potassium phthalimido-N-hydroxylate in water as another base though by use of 10% excess of the reagent malononitrile, 3 which however creates additional wastes when recycling the catalyst.…”

Section: Introductionmentioning

confidence: 99%

Ball milling for the quantitative and specific solvent-free Knoevenagel condensation + Michael addition cascade in the synthesis of various 2-amino-4-aryl-3-cyano-4H-chromenes without heating

et al. 2014

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Fluoride ion-catalyzed conjugate addition for easy synthesis of 3-sulfanylpropionic acid from thiol and α,β-unsaturated carboxylic acid

Cited by 22 publications

References 44 publications

Covalent Modifiers: A Chemical Perspective on the Reactivity of α,β-Unsaturated Carbonyls with Thiols via Hetero-Michael Addition Reactions

Covalent Modifiers: A Chemical Perspective on the Reactivity of α,β-Unsaturated Carbonyls with Thiols via Hetero-Michael Addition Reactions

Design of CID-cleavable protein cross-linkers: identical mass modifications for simpler sequence analysis

Ball milling for the quantitative and specific solvent-free Knoevenagel condensation + Michael addition cascade in the synthesis of various 2-amino-4-aryl-3-cyano-4H-chromenes without heating

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