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Palladium-catalyzed deracemization of allylic carbonates in water with formation of allylic alcohols: hydrogen carbonate ion as nucleophile in the palladium-catalyzed allylic substitution and kinetic resolution.

Journal of the American Chemical Society

Lüssem BJ, Gais HJ.
PMID: 12785831
J Am Chem Soc. 2003 May 21;125(20):6066-7. doi: 10.1021/ja034109t.

The palladium-catalyzed deracemization of racemic cyclic and acyclic allylic methyl carbonates in water in the presence of N,N'-(1R,2R)-1,2-cyclohexanediylbis[2-(diphenylphophino)benzamide] proceeds with high enantioselectivities to give the corresponding allylic alcohols in high yields. This deracemization involves a palladium-catalyzed allylic substitution with...

Functionalized chiral vinyl aminosulfoxonium salts: asymmetric synthesis and application to the synthesis of enantiopure unsaturated prolines, beta,gamma-dehydro amino acids, and cyclopentanoid keto aminosulfoxonium ylides.

Journal of the American Chemical Society

Tiwari SK, Gais HJ, Lindenmaier A, Babu GS, Raabe G, Reddy LR, Köhler F, Günter M, Koep S, Iska VB.
PMID: 16734492
J Am Chem Soc. 2006 Jun 07;128(22):7360-73. doi: 10.1021/ja061152i.

Methylation of the enantiopure functionalized vinyl sulfoximines 5a-e and 14a-d followed by a F- ion or DBU-mediated isomerization of the vinyl aminosulfoxonium salts 7a-e and 15a-d, respectively, gave the allyl aminosulfoxonium salts 10a-e and 17a-d, respectively. A concomitant intramolecular...

Chiral fluorinated α-sulfonyl carbanions: enantioselective synthesis and electrophilic capture, racemization dynamics, and structure.

Chemistry (Weinheim an der Bergstrasse, Germany)

Hellmann G, Hack A, Thiemermann E, Luche O, Raabe G, Gais HJ.
PMID: 23401229
Chemistry. 2013 Mar 18;19(12):3869-97. doi: 10.1002/chem.201204014. Epub 2013 Feb 10.

Enantiomerically pure triflones R(1) CH(R(2) )SO2 CF3 have been synthesized starting from the corresponding chiral alcohols via thiols and trifluoromethylsulfanes. Key steps of the syntheses of the sulfanes are the photochemical trifluoromethylation of the thiols with CF3 Hal (Hal=halide)...

WITHDRAWN: Corrigendum to "A lectin from the Chinese bird-hunting spider binds sialic acids".

Carbohydrate research

Siebert HC, Lu SY, Wechselberger R, Born K, Eckert T, Liang S, der Lieth CW, Jiménez-Barbero J, Schauer R, G Vliegenthart JF, Lütteke T, André S, Kaltner H, Gabius HJ, Kožár T.
PMID: 20176345
Carbohydr Res. 2010 Feb 20; doi: 10.1016/j.carres.2009.12.027. Epub 2010 Feb 20.

The Publisher regrets that this article is an accidental duplication of an article that has already been published, doi: 10.1016/j.carres.2010.01.003. The duplicate article has therefore been withdrawn.

Fluorinated Carbohydrates as Lectin Ligands: Synthesis of OH/F-Substituted N-Glycan Core Trimannoside and Epitope Mapping by 2D STD-TOCSYreF NMR spectroscopy.

Chemistry (Weinheim an der Bergstrasse, Germany)

Diercks T, Infantino AS, Unione L, Jiménez-Barbero J, Oscarson S, Gabius HJ.
PMID: 30276889
Chemistry. 2018 Oct 22;24(59):15761-15765. doi: 10.1002/chem.201803217. Epub 2018 Oct 01.

Glycan-protein interactions play an important role in a broad range of physiological processes, raising interest to elucidate the structural interplay. Yet, their dynamic nature limits the analysis by crystallography, whereas NMR spectroscopy suffers from the low

Why Do Membranes of Some Unhealthy Cells Adopt a Cubic Architecture?.

ACS central science

Xiao Q, Wang Z, Williams D, Leowanawat P, Peterca M, Sherman SE, Zhang S, Hammer DA, Heiney PA, King SR, Markovitz DM, André S, Gabius HJ, Klein ML, Percec V.
PMID: 28058284
ACS Cent Sci. 2016 Dec 28;2(12):943-953. doi: 10.1021/acscentsci.6b00284. Epub 2016 Dec 05.

Nonlamellar lipid arrangements, including cubosomes, appear in unhealthy cells, e.g., when they are subject to stress, starvation, or viral infection. The bioactivity of cubosomes-nanoscale particles exhibiting bicontinuous cubic structures-versus more common vesicles is an unexplored area due to lack...

Vision while the eyes move: Getting the full picture.

Science advances

Fabius JH, Van der Stigchel S.
PMID: 34301609
Sci Adv. 2021 Jul 23;7(30). doi: 10.1126/sciadv.abk0043. Print 2021 Jul.

Visual information is continuously sampled from our environment, even as the eyes move, which helps the visual system create a stable view of the world.

Structural Characterization of Rat Galectin-5, an N-Tailed Monomeric Proto-Type-like Galectin.

Biomolecules

Ruiz FM, Medrano FJ, Ludwig AK, Kaltner H, Shilova NV, Bovin NV, Gabius HJ, Romero A.
PMID: 34944498
Biomolecules. 2021 Dec 09;11(12). doi: 10.3390/biom11121854.

Galectins are multi-purpose effectors acting via interactions with distinct counterreceptors based on protein-glycan/protein recognition. These processes are emerging to involve several regions on the protein so that the availability of a detailed structural characterization of a full-length galectin is...

Fluorinated Carbohydrates as Lectin Ligands: Simultaneous Screening of a Monosaccharide Library and Chemical Mapping by .

The Journal of organic chemistry

Martínez JD, Manzano AI, Calviño E, Diego A, Rodriguez de Francisco B, Romanò C, Oscarson S, Millet O, Gabius HJ, Jiménez-Barbero J, Cañada FJ.
PMID: 33258593
J Org Chem. 2020 Dec 18;85(24):16072-16081. doi: 10.1021/acs.joc.0c01830. Epub 2020 Dec 01.

Molecular recognition of carbohydrates is a key step in essential biological processes. Carbohydrate receptors can distinguish monosaccharides even if they only differ in a single aspect of the orientation of the hydroxyl groups or harbor subtle chemical modifications. Hydroxyl-by-fluorine...

Chiral Lithiated Allylic α-Sulfonyl Carbanions: Experimental and Computational Study of Their Structure, Configurational Stability, and Enantioselective Synthesis.

Chemistry (Weinheim an der Bergstrasse, Germany)

Gerhards F, Griebel N, Runsink J, Raabe G, Gais HJ.
PMID: 26494207
Chemistry. 2015 Dec 01;21(49):17904-20. doi: 10.1002/chem.201503123. Epub 2015 Oct 23.

X-ray crystal structure analysis of the lithiated allylic α-sulfonyl carbanions [CH2 CHC(Me)SO2 Ph]Li⋅diglyme, [cC6 H8 SO2 tBu]Li⋅PMDETA and [cC7 H10 SO2 tBu]Li⋅PMDETA showed dimeric and monomeric CIPs, having nearly planar anionic C atoms, only OLi bonds, almost planar allylic...

Brain lesion-induced alteration of selected phenotypic properties of spleen macrophages and their partial restoration in the course of foreign body reaction against intraperitoneally implanted polymers.

Journal of materials science. Materials in medicine

Smetana K, Petrovický P, Zach P, Nemcová V, Jelínková M, Vacík J, Gabius HJ.
PMID: 15348128
J Mater Sci Mater Med. 1999 Jul;10(7):425-9. doi: 10.1023/a:1008931231762.

A lesion in the dorsoposterior part of the rat brain septum is known to exert an inhibitory effect on the delayed skin hypersensitivity and incorporation of radiolabeled thymidine into the lymphoid organs. To determine whether distinct properties of macrophages...

Dynamic behavior of chiral sulfonimidoyl-substituted allyl and alkyl (dimethylamino)titanium(IV) complexes: metallotropic shift, reversible beta-hydride elimination/reinsertion, and ab initio calculations of allyl and alkyl aminosulfoxonium ylides.

Journal of the American Chemical Society

Gais HJ, Bruns PR, Raabe G, Hainz R, Schleusner M, Runsink J, Babu GS.
PMID: 15869283
J Am Chem Soc. 2005 May 11;127(18):6617-31. doi: 10.1021/ja0433828.

Variable-temperature (1)H and (13)C NMR spectroscopy of the sulfonimidoyl-substituted allyltitanium(IV) complexes E-1a-c and Z-1a-c, which carry diethylamino groups at the Ti atom, revealed a fast 1,3-C,N-shift of the Ti atom, leading to an equilibrium between the epimeric Calpha-titanium allyl...

Showing 1 to 12 of 55 entries