Direct incorporation of unprotected ketone groups into peptides during solid-phase synthesis: Application to the one-step modification of peptides with two different biophysical probes for FRET

Small molecule–DNA hybrids can be synthesized in a one-pot fashion and in good yields by coupling multiazide cores to alkyne-modified DNAs on a solid support using click chemistry.

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DMAP-assisted sulfonylation as an efficient step for the methylation of primary amine motifs on solid support

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.13.81 ◽

2017 ◽

Vol 13 ◽

pp. 806-816 ◽

Cited By ~ 6

Author(s):

Johnny N Naoum ◽

Koushik Chandra ◽

Dorit Shemesh ◽

R Benny Gerber ◽

Chaim Gilon ◽

...

Keyword(s):

Dft Calculations ◽

Primary Amine ◽

Energy Barrier ◽

Solid Phase Synthesis ◽

State Of The Art ◽

Solid Phase ◽

Solid Support ◽

Somatostatin Analogue ◽

Phase Synthesis ◽

The One

Several multistep strategies were developed to ensure single methylation of amines on solid support. These strategies rely on the introduction of the o-NBS protecting/activating group as a key step. We found that the state-of-the-art strategies fail for the methylation of several primary amine motifs, largely due to inefficient sulfonylation. Here we show that using the superior nucleophilic base DMAP instead of the commonly used base collidine as a sulfonylation additive is essential for the introduction of the o-NBS group to these amine motifs. DFT calculations provide an explanation by showing that the energy barrier of the DMAP intermediate is significantly lower than the one of the collidine. We demonstrate that using DMAP as a sole additive in the sulfonylation step results in an overall effective and regioselective N-methylation. The method presented herein proved highly efficient in solid-phase synthesis of a somatostatin analogue bearing three N α-methylation sites that could not be synthesized using the previously described state-of-the-art methods.

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One-step solid phase synthesis of a highly efficient and robust cobalt pentlandite electrocatalyst for the oxygen evolution reaction

Journal of Materials Chemistry A ◽

10.1039/c6ta07962h ◽

2016 ◽

Vol 4 (47) ◽

pp. 18314-18321 ◽

Cited By ~ 70

Author(s):

Mohammad Al-Mamun ◽

Yun Wang ◽

Porun Liu ◽

Yu Lin Zhong ◽

Huajie Yin ◽

...

Keyword(s):

Oxygen Evolution ◽

Oxygen Evolution Reaction ◽

Solid Phase Synthesis ◽

Solid Phase ◽

Phase Synthesis ◽

Highly Efficient ◽

One Step

One-step concurrent growth of a Co9S8/carbon nanosheet composite as an efficient and robust oxygen evolution electrocatalyst.

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Initiation and development of exothermic reactions during solid-phase synthesis under explosive loading

Thermal Science ◽

10.2298/tsci19s2505t ◽

2019 ◽

Vol 23 (Suppl. 2) ◽

pp. 505-511 ◽

Cited By ~ 1

Author(s):

Vladimir Tolkachev ◽

Oksana Ivanova ◽

Sergey Zelepugin

Keyword(s):

Solid Phase Synthesis ◽

Solid Phase ◽

Experimental Studies ◽

High Heat ◽

Bottom Part ◽

Phase Synthesis ◽

Exothermic Reactions ◽

Porous Aluminum ◽

The One ◽

Faster Development

The previous numerical and experimental studies of the solid-phase synthesis of porous reactive mixtures (Al-S and Al-Tf) placed into cylindrical ampoules subjected to explosive detonation revealed the sharp increase in temperatures and pressures. The results have shown that high heat release and high increase in pressure due to exothermic reactions in the mixture, on the one hand, promote the faster development of reactions and, on the other hand, contribute to the formation of a gas phase that, in turns, may lead to the damage or even fracture of ampoules. This problem is solved by adding an inert porous aluminum layer to the bottom part of the mixture. Computations are carried out using the model of a multicomponent medium and the finite element method. Numerical simulation has shown that in this case the fracture of cylindrical ampoules is not observed.

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