- CHEMOSELECTIVE SENSITIVITY BOOSTER FOR TAGGING A PEPTIDE, PEPTIDE CONJUGATE, OR SIMILAR REACTIVE MOLECULE
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The invention pertains to chemoselective sensitivity booster for tagging a peptide, peptide conjugate, or similar reactive molecule for analysis of a peptide, protein, antibody, protein bioconjugate, antibody bioconjugate, and similar analytes. The sensitivity booster comprises of sp2 or sp3 nitrogen centers in combination with hydrophobic carbon chains linked with an electrophile or nucleophile for attachment with a peptide, peptide conjugate, or molecules with similar reactivity.
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Page/Page column 24; 25
(2020/12/29)
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- Sensitivity booster for mass detection enables unambiguous analysis of peptides, proteins, antibodies, and protein bioconjugates
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A chemical tag enhances peptide detection by multiple orders in mass spectrometry. The substantial improvement in the peptide mapping along with simplified and enhanced fragmentation pattern enables the unambiguous sequencing of a protein and antibody. The chemoselective sensitivity booster provides a tool for remarkably improved analysis of protein bioconjugates.
- Singudas, Rohith,Reddy, Neelesh C.,Rai, Vishal
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supporting information
p. 9979 - 9982
(2019/08/22)
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- N-Propargylation of secondary amines directly using calcium carbide as an acetylene source
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A one-pot N-propargylation of secondary amines has been achieved by heating the amine with formaldehyde and calcium carbide in DMSO in the presence of CuCl as a catalyst. Fifteen examples of propargylic tertiary amines, 12 of which are novel, were efficiently prepared in yields of 65-84%. The advantages of the method are broad substrate scope and a simple work-up procedure.
- Fu, Rugang,Li, Zheng
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p. 341 - 345
(2017/06/19)
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- Synthesis of novel triazole-linked mefloquine derivatives: Biological evaluation against Plasmodium falciparum
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Using 2,8-bis(trifluoromethyl)quinoline, the pharmacophore of mefloquine, as scaffold, eleven novel triazole-linked compounds have been synthesised by the application of CuAAC chemistry. The in vitro biological activity of the compounds on the Plasmodium falciparum chloroquine-sensitive strain NF54 was then determined. The compounds all showed IC50s in the lower μM range with (1R,3S,5R)-N-{[1-(2,8-bis(trifluoromethyl)quinoline-4-yl)-1H-1,2,3-triazol-4-yl]methyl}adamantan-2-amine (29) exhibiting the best activity of 1.00 μM.
- Hamann, Anton R.,De Kock, Carmen,Smith, Peter J.,Van Otterlo, Willem A.L.,Blackie, Margaret A.L.
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supporting information
p. 5466 - 5469
(2015/01/08)
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- A 1,3-amino group migration route to form acrylamidines
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A novel 1,3-amino group migration strategy for the synthesis of acrylamidines is presented. Cu(i) catalyzed reaction of N,N-disubstituted propargylamine with tosylazide generates a highly reactive ketenimine intermediate which is trapped by a tethered amino group leading to the rearrangement reaction.
- Chauhan, Dinesh Pratapsinh,Varma, Sreejith Jayasree,Vijeta, Arjun,Banerjee, Pallavi,Talukdar, Pinaki
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supporting information
p. 323 - 325
(2014/01/06)
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- Influence of the acetylenic substituent on the intramolecular carbolithiation of alkynes
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The intramolecular carbolithiation of a series of propargylic ethers has been performed to evaluate the influence of the terminal substituent on the efficiency and the stereochemical outcome of the cyclization. Our results show that only 5-exo-dig cyclizations are observed, and dihydrobenzofurans are obtained exclusively. Depending on the nature of the terminal substituent, two cases can be considered. If the terminal substituent carried by the acetylenic carbon atom is itself a carbon atom, the cyclization can occur provided the terminal propargylic position bears a coordinating element and is at least disubstituted. When the cyclization occurs, it follows an anti-carbolithiation pathway and thus leads to the E isomer of the exocyclic double bond. Only in one case (Ph) was a mixture of the E and Z isomers of the resulting olefin recovered. The cyclization can also take place if the alkyne is directly substituted by S or Si, provided the cyclization conditions are tuned. In the case of the trimethylsilyl substituent, a syn-carbolithiation was observed. If the double bond is recovered, in most cases, in the exocyclic position, the products can aromatize directly for SPh-substituted substrate 24. Furthermore, in the two latter cases, when alkylation of the vinyllithium intermediate is performed, isomerization of the double bond seems instantaneous. Copyright
- Girard, Anne-Lise,Lhermet, Rudy,Fressigne, Catherine,Durandetti, Muriel,Maddaluno, Jacques
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scheme or table
p. 2895 - 2905
(2012/06/29)
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- Copper(I)-catalysed deacetylenative cross-coupling reaction of terminal alkynes with propargylic amines via C(sp)-C(sp3) bond cleavage
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The catalytic deacetylenative coupling reaction of terminal alkynes with various N-substituted propargylic amines proceeded in the presence of CuCl (10 mol%) and NaPO(4 equiv) in THF at 130 °C to give the corresponding substituted propargylic amines in go
- Kim, Yongeun,Nakamura, Hiroyuki
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supporting information; experimental part
p. 1686 - 1690
(2012/07/17)
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- 4 ( 1H) -PYRIDINONE DERIVATIVES AND THEIR USE AS ANTIMALARIA AGENTS
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4-pyridone (4-pyridinone) derivatives of Formula (I) and pharmaceutically acceptable derivatives thereof, processes for their preparation, pharmaceutical formulations thereof and their use in chemotherapy of certain parasitic infections such as malaria, are provided.
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Page/Page column 39
(2010/08/08)
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- Copper(I)-catalyzed substitution reactions of propargylic amines: Importance of C(sp)-C(sp3) bond cleavage in generation of iminium intermediates
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Substitution reactions of propargylic amines proceed in the presence of copper(I) catalysts. Mechanistic studies showed that C(sp)?C(sp3) bond cleavage assisted by nitrogen lone-pair electrons is essential for the reaction, and the resulting iminium intermediates undergo amine exchange, aldehyde exchange, and alkyne addition reactions. Because iminium intermediates are key to aldehyde?alkyne?amine (A3) coupling reactions, this transformation is effective not only for reconstruction of propargylic amines but also for chiral induction of racemic compounds in the presence of chiral catalysts.
- Sugiishi, Tsuyuka,Kimura, Akifumi,Nakamura, Hiroyuki
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supporting information; experimental part
p. 5332 - 5333
(2010/07/04)
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- A gallium-catalyzed cycloisomerization/Friedel-Crafts tandem
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Under noble (Au, Pt, Ru) and group 13 (Ga, In) metals catalysis, 1,6-arenynes rearrange to give 1,2-dihydronaphthalenes in a high yielding, regiocontrolled fashion. When the reaction is carried out in the presence of electron-rich arenes (anisole, phenol, indole derivatives), Friedel-Crafts addition may follow the cycloisomerization step. Only GaX3 salts proved able to catalyze these two C-C bond formation events. This specificity of gallium has been exploited for the synthesis of valuable polycyclic compounds that would be very difficult to prepare otherwise. For instance, tetrahydroisoquinolines and tetrahydrobenzoazepines have been obtained by selective 6-exo-dig or 7-endo-dig cyclization of N-tethered 1,6-arenynes. DFT calculations were carried out to shed light on the mechanism and provide a rationale for this regiodivergency. Computations also reveal the fundamental role of the tether in the stabilization of carbocationic species. Differential reactivities of other types of substrates in gallium- and gold-catalyzed cascades are also exposed, showing that the two approaches are complementary. In particular, bimolecular Friedel-Crafts additions are facilitated under gallium catalysis.
- Li, Hui-Jing,Guillot, Regis,Gandon, Vincent
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supporting information; experimental part
p. 8435 - 8449
(2011/03/19)
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- Tuning topochemical polymerization of diacetylenes: A joint synthetic, structural, photophysical, and theoretical study of a series ofanalogues of aknown reactive monomer, 1,6-bis(diphenylamino)-2,4-hexadiyne (THD)
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Several analogues of 1,6-bis(diphenylamino)-2,4-hexadiyne (THD) have been prepared and their thermal and photochemical solid-state polymerization reactivity assessed. The compounds involved in this investigation are 1,6-bis(dibenzylamino)-2,4-hexadiyne (1
- Deschamps, Jerome,Balog, Mirela,Boury, Bruno,Yahia, Mouna Ben,Filhol, Jean-Sebastien,Van Der Lee, Arie,Al Choueiry, Antoine,Barisien, Thierry,Legrand, Laurent,Schott, Michel,Dutremez, Sylvain G.
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scheme or table
p. 3961 - 3982
(2012/01/05)
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- Synthesis of α-amino acids by reaction of aziridine-2-carboxylic acids with carbon nucleophiles
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A variety of homochiral α-amino acids have been prepared in good yield via regioselective reaction of higher order cuprates with (2S)-N-para-toluenesulfonylaziridine-2-carboxylic acid 4. The reaction was much less regioselective and low yielding when higher order cuprates were reacted with the more hindered aziridine carboxylic acid 30, the principal products being protected β-amino acids. Reaction of lithium trimethylsilylacetylide with the aziridine acid 30, however, gave a protected α-amino acid which was converted to the protected isoleucine ester 37. The Royal Society of Chemistry 2006.
- Beresford, Kenneth J. M.,Church, Nicola J.,Young, Douglas W.
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p. 2888 - 2897
(2008/02/08)
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- New Synthesis of Propargylic Amines from 2-(Bromomethyl)aziridines. Intermediacy of 3-Bromoazetidinium Salts
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A new, efficient, and straightforward synthesis provides propargylamines in high overall yields (64-77%) by transformation of 1-(arylmethyl)-2-(bromomethyl)aziridines into N,N-di(arylmethyl)N-(2-propynyl)amines via N-(2,3-dibromopropyl)amines and N-(2-bromo-2-propenyl)amines. The conversion of N-(2,3-dibromopropyl)amines into N-(2-bromo-2-propenyl)amines is based on a novel analogue of the Hofmann elimination. A Yamaguchi-Hirao alkylation, a Sonogashira coupling, or a hydroarylation reaction further functionalized these propargylamines toward potentially interesting compounds for medicinal and agrochemical use.
- D'Hooghe, Matthias,Van Brabandt, Willem,De Kimpe, Norbert
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p. 2703 - 2710
(2007/10/03)
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- Copper reagents: A new and efficient solution for the selective addition of metallated propargylic amines to aldehydes
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(Matrix presented) Anti α-amino-homopropargylic alcohols are prepared by addition of metallated propargylic amines to aldehydes. Among the four organometallic (Ll, Zn, Ti, Cu) derivatives used, the most effective are the copper reagents.
- Bernaud, Frederic,Vrancken, Emmanuel,Mangeney, Pierre
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p. 2567 - 2569
(2007/10/03)
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