- Design, synthesis, and biological activity of novel triazole amino acids used to probe binding interactions between ligand and neutral amino acid transport protein SN1
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Novel triazole amino acids were synthesized as probes to investigate ligand-protein binding interactions of the neutral amino acid transporter SN1. The bonding hypothesis to be tested was that the side chains of endogenous substrates are acting as H-bond acceptors. Although limited inhibition of 3H-l-glutamine uptake by SN1 expressing oocytes was observed, the synthetic compounds show a trend that suggests a hydrogen bond interaction just outside the endogenous ligand binding pocket.
- Gajewski, Mariusz,Seaver, Ben,Esslinger, C. Sean
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Read Online
- Simple preparation of new [18F]F-labeled synthetic amino acid derivatives with two click reactions in one-pot and SPE purification
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New [18F]fluorinated 1,2,3-triazolyl amino acid derivatives were efficiently prepared from Huisgen 1,3-dipolar cycloaddition reactions, well known as click reaction. We developed two simultaneous click reactions in one-pot with a simple solid-p
- Yook, Cheol-Min,Lee, Sang Ju,Oh, Seung Jun,Ha, Hyun-Joon,Lee, Jong Jin
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p. 317 - 326
(2015/08/03)
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- Stable triazolylphosphonate analogues of phosphohistidine
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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. Springer-Verlag 2011.
- Mukai, Shin,Flematti, Gavin R.,Byrne, Lindsay T.,Besant, Paul G.,Attwood, Paul V.,Piggott, Matthew J.
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p. 857 - 874
(2012/10/07)
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- A fluorogenic probe for the catalyst-free detection of azide-tagged molecules
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Fluorogenic reactions in which non- or weakly fluorescent reagents produce highly fluorescent products can be exploited to detect a broad range of compounds including biomolecules and materials. We describe a modified dibenzocyclooctyne that under catalyst-free conditions undergoes fast strain-promoted cycloadditions with azides to yield strongly fluorescent triazoles. The cycloaddition products are more than 1000-fold brighter compared to the starting cyclooctyne, exhibit large Stokes shift, and can be excited above 350 nm, which is required for many applications. Quantum mechanical calculations indicate that the fluorescence increase upon triazole formation is due to large differences in oscillator strengths of the S0 S 1 transitions in the planar C2v-symmetric starting material compared to the symmetry-broken and nonplanar cycloaddition products. The new fluorogenic probe was successfully employed for labeling of proteins modified by an azide moiety.
- Friscourt, Frederic,Fahrni, Christoph J.,Boons, Geert-Jan
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p. 18809 - 18815
(2013/01/15)
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- PHOSPHOHISTIDINE ANALOGS
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The present invention relates to the phosphohistidine analogs of the present invention which of the formula (I) and the hapten containing the residue of same. It also relates to the hapten conjugated to a carrier molecule and the isolated antibodies raise
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Page/Page column 62-63
(2012/04/10)
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- Development of stable phosphohistidine analogues
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Protein phosphorylation is one of the most common and extensively studied posttranslational modifications (PTMs). Compared to the O-phosphorylation of Ser, Thr, and Tyr residues, our understanding of histidine phosphorylation is relatively limited, partic
- Kee, Jung-Min,Villani, Bryeanna,Carpenter, Laura R.,Muir, Tom W.
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supporting information; experimental part
p. 14327 - 14329
(2010/12/25)
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- A concise route to L-azidoamino acids: L-azidoalanine, L-azidohomo-alanine and L-azidonorvaline
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A simple and highly efficient synthetic route to three homologous azidoamino acids, starting from inexpensive, commercially available, protected natural amino acids is reported. The products can be used to introduce bioorthogonal handles into proteins. Ge
- Roth, Stefanie,Thomas, Neil R.
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scheme or table
p. 607 - 609
(2010/09/18)
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- The synthesis of chiral 3-oxo-6-[(phenylmethoxy)-carbonyl]-2-piperazineacetic acid esters designed for the presentation of an aspartic acid side chain. A subsequent novel Friedel Crafts reaction
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The syntheses of (2S, 6R)-, and (2S, 6S)-3-oxo-6-[(phenylmethoxy)carbonyl]-2-piperazineacetic acid methyl esters from L- or D-serine and dimethyl-D-malate are described. Acylation of the (2S, 6S) isomer with 3-methoxyphenylacetyl chloride, hydrogenolysis of the benzyl ester, followed by treatment with oxalyl chloride then aluminum chloride led to an unexpected tricyclic product into which a C2O2 unit had been incorporated.
- Kogan,Rawson
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p. 7089 - 7092
(2007/10/02)
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