Diverse Reactions of Vinyl Diazo Compounds with Quinone Oxonium Ions, Quinone Imine Ketals, and Eschenmoser’s Salt

ACS Catalysis ◽  
2021 ◽  
pp. 9869-9874
Author(s):  
Haifeng Zheng ◽  
Kan Wang ◽  
Isa Faghihi ◽  
Wendell P. Griffith ◽  
Hadi Arman ◽  
...  
Keyword(s):  
Quinone Imine ◽  
Diazo Compounds ◽  
Oxonium Ions

New catalysts for the reduction of aromatic diazo compounds by alcohols to hydrocarbons

1983 ◽  
Vol 32 (4) ◽  
pp. 858-861 ◽  
Author(s):  
V. S. Lenenko ◽  
A. P. Borisov ◽  
V. D. Makhaev ◽  
E. I. Mysov ◽  
V. B. Shur ◽  
...  
Keyword(s):  
Diazo Compounds

Rhodium-catalyzed enone carbonyl directed C–H activation for the synthesis of indanones containing all-carbon quaternary centers

2021 ◽  
Vol 8 (7) ◽  
pp. 1447-1453
Author(s):  
Jiang Lou ◽  
Wenjia Han ◽  
Zhuqing Liu ◽  
Jiaqi Xiao
Keyword(s):  
Diazo Compounds ◽  
Quaternary Centers ◽  
Ketene Dithioacetals

Rhodium(iii)-catalyzed enone carbonyl directed C–H activation/annulation of α-aroyl ketene dithioacetals with diazo compounds has been realized for the synthesis of β-quaternary indanones.

Synthesis of pyrazolo[1,5-c]quinazoline derivatives through the copper-catalyzed domino reaction of o-alkenyl aromatic isocyanides with diazo compounds

2020 ◽  
Vol 56 (55) ◽  
pp. 7665-7668 ◽  
Author(s):  
Lu Liu ◽  
Lei Li ◽  
Shukuan Mao ◽  
Xin Wang ◽  
Ming-Dong Zhou ◽  
...  
Keyword(s):  
Diazo Compounds ◽  
Domino Reaction ◽  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
Quinazoline Derivatives

Various o-alkenyl aromatic isocyanides were prepared from readily available reactants for their double annulation with diazo compounds for a one-pot synthesis of pyrazolo[1,5-c]quinazolines under mild reaction conditions.

scholarly journals ON A POSSIBLE ASYMMETRY OF ALIPHATIC DIAZO COMPOUNDS. II

1922 ◽  
Vol 52 (2) ◽  
pp. 485-494
Author(s):  
P.A. Levene ◽  
L.A. Mikeska
Keyword(s):  
Diazo Compounds

scholarly journals Oxonium Ion Guided Analysis of Quantitative Proteomics Data Reveals Site-Specific O-Glycosylation of Anterior Gradient Protein 2 (AGR2)

2021 ◽  
Vol 22 (10) ◽  
pp. 5369
Author(s):  
Martina Pirro ◽  
Yassene Mohammed ◽  
Arnoud H. de Ru ◽  
George M. C. Janssen ◽  
Rayman T. N. Tjokrodirijo ◽  
...  
Keyword(s):  
Cell Lines ◽  
Quantitative Proteomics ◽  
Glycosylation Site ◽  
Total Cell ◽  
Tandem Mass ◽  
Proteomics Data ◽  
Site Specific ◽  
Oxonium Ions ◽  
Tandem Mass Tag ◽  
Colorectal Cancer Cell Lines

Developments in mass spectrometry (MS)-based analyses of glycoproteins have been important to study changes in glycosylation related to disease. Recently, the characteristic pattern of oxonium ions in glycopeptide fragmentation spectra had been used to assign different sets of glycopeptides. In particular, this was helpful to discriminate between O-GalNAc and O-GlcNAc. Here, we thought to investigate how such information can be used to examine quantitative proteomics data. For this purpose, we used tandem mass tag (TMT)-labeled samples from total cell lysates and secreted proteins from three different colorectal cancer cell lines. Following automated glycopeptide assignment (Byonic) and evaluation of the presence and relative intensity of oxonium ions, we observed that, in particular, the ratio of the ions at m/z 144.066 and 138.055, respectively, could be used to discriminate between O-GlcNAcylated and O-GalNAcylated peptides, with concomitant relative quantification between the different cell lines. Among the O-GalNAcylated proteins, we also observed anterior gradient protein 2 (AGR2), a protein which glycosylation site and status was hitherto not well documented. Using a combination of multiple fragmentation methods, we then not only assigned the site of modification, but also showed different glycosylation between intracellular (ER-resident) and secreted AGR2. Overall, our study shows the potential of broad application of the use of the relative intensities of oxonium ions for the confident assignment of glycopeptides, even in complex proteomics datasets.

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