Synthesis of Benzyl Esters Using 2-Benzyloxy-1-methylpyridinium Triflate

Histidine-phosphorylated proteins and the corresponding kinases are important components of bacterial and eukaryotic cell-signalling pathways, and are therefore potential drug targets. The study of these biomolecules has been hampered by the lability of the phosphoramidate functional group in the phosphohistidines and the lack of generic antibodies. Herein, the design and concise synthesis of stable triazolylphosphonate analogues of N1- and N3-phosphohistidine, and derivatives suitable for bioconjugation, are described.

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“…1 (Nakata et al 1996) -19.0°(c 1.0, CHCl 3 )]. The NMR data are similar to those reported (Tummatorn et al 2007). …”

Section: (S)-benzyl 3-hydroxy-2-(t-butoxycarbonylamino) Propanoate [Bsupporting

confidence: 88%

Stable triazolylphosphonate analogues of phosphohistidine

et al. 2011

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“…Opting to reduce the number of synthetic steps by purchasing isotopic alanine benzyl ester commercially nearly doubles the cost, however. Several other straightforward synthetic routes to produce benzyl esters from carboxylic acids exist …”

Section: Resultsmentioning

confidence: 99%

Development and characterization of novel 8‐plex DiLeu isobaric labels for quantitative proteomics and peptidomics

Frost

Greer

Xiang

et al. 2015

Rapid Comm Mass Spectrometry

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Rationale Relative quantification of proteins via their enzymatically digested peptide products determines disease biomarker candidate lists in discovery studies. Isobaric label-based strategies using TMT and iTRAQ allow for up to 10 samples to be multiplexed in one experiment, but their expense limits their use. The demand for cost-effective tagging reagents capable of multiplexing many samples led us to develop an 8-plex version of our isobaric labeling reagent, DiLeu. Methods The original 4-plex DiLeu reagent was extended to an 8-plex set by coupling isotopic variants of dimethylated leucine to an alanine balance group designed to offset the increasing mass of the label’s reporter group. Tryptic peptides from a single protein digest, a protein mixture digest, and Saccharomyces cerevisiae lysate digest were labeled with 8-plex DiLeu and analyzed via nanoLC-MS2 on a Q-Exactive Orbitrap mass spectrometer. Characteristics of 8-plex DiLeu-labeled peptides, including quantitative accuracy and fragmentation, were examined. Results An 8-plex set of DiLeu reagents with 1 Da-spaced reporters was synthesized at a yield of 36%. The average cost to label eight 100 μg peptide samples was calculated to be approximately $15. Normalized collision energy tests on the Q-Exactive revealed that a higher-energy collisional dissociation value of 27 generated the optimum number of high-quality spectral matches. Relative quantification of DiLeu-labeled peptides yielded normalized median ratios accurate to within 12% of their expected values. Conclusions Cost-effective 8-plex DiLeu reagents can be synthesized and applied to relative peptide and protein quantification. These labels increase the multiplexing capacity of our previous 4-plex implementation without requiring high-resolution instrumentation to resolve reporter ion signals.

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“…These results can be considered to be more consistent with an S N 2‐type reaction, although kinetic studies have not been conducted. The reaction would involve the formation of a hydrogen bond between the proton of the carboxylic acid and a nitrogen atom of TriBOT, which activates the two species and leads to an S N 2‐type reaction to give benzyl esters (Scheme ) 9…”

Section: Resultsmentioning

confidence: 99%

O‐Benzylation of Carboxylic Acids Using 2,4,6‐Tris(benzyloxy)‐1,3,5‐triazine (TriBOT) under Acidic or Thermal Conditions

et al. 2015

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Metal–organic polyhedra (MOPs) or frameworks (MOFs) based on Cr3+ are notoriously difficult to synthesize, especially as crystals large enough to be suitable for characterization of the structure or properties. It is now shown that the co‐existence of In3+ and Cr3+ induces a rapid crystal growth of large single crystals of heterometallic In‐Cr‐MOPs with the [M8L12] (M=In/Cr, L=dinegative 4,5‐imidazole‐dicarboxylate) cubane‐like structure. With a high concentration of protons from 12 carboxyl groups decorating every edge of the cube and an extensive H‐bonded network between cubes and surrounding H2O molecules, the newly synthesized In‐Cr‐MOPs exhibit an exceptionally high proton conductivity (up to 5.8×10−2 S cm−1 at 22.5 °C and 98 % relative humidity, single crystal).

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Synthesis of Benzyl Esters Using 2-Benzyloxy-1-methylpyridinium Triflate

Cited by 44 publications

References 10 publications

Stable triazolylphosphonate analogues of phosphohistidine

Stable triazolylphosphonate analogues of phosphohistidine

Development and characterization of novel 8‐plex DiLeu isobaric labels for quantitative proteomics and peptidomics

O‐Benzylation of Carboxylic Acids Using 2,4,6‐Tris(benzyloxy)‐1,3,5‐triazine (TriBOT) under Acidic or Thermal Conditions

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