33173-55-6Relevant academic research and scientific papers
Modular click chemistry libraries for functional screens using a diazotizing reagent
Meng, Genyi,Guo, Taijie,Ma, Tiancheng,Zhang, Jiong,Shen, Yucheng,Sharpless, Karl Barry,Dong, Jiajia
, p. 86 - 89 (2019/11/13)
Click chemistry is a concept in which modular synthesis is used to rapidly find new molecules with desirable properties1. Copper(i)-catalysed azide–alkyne cycloaddition (CuAAC) triazole annulation and sulfur(vi) fluoride exchange (SuFEx) catalysis are widely regarded as click reactions2–4, providing rapid access to their products in yields approaching 100% while being largely orthogonal to other reactions. However, in the case of CuAAC reactions, the availability of azide reagents is limited owing to their potential toxicity and the risk of explosion involved in their preparation. Here we report another reaction to add to the click reaction family: the formation of azides from primary amines, one of the most abundant functional groups5. The reaction uses just one equivalent of a simple diazotizing species, fluorosulfuryl azide6–11 (FSO2N3), and enables the preparation of over 1,200 azides on 96-well plates in a safe and practical manner. This reliable transformation is a powerful tool for the CuAAC triazole annulation, the most widely used click reaction at present. This method greatly expands the number of accessible azides and 1,2,3-triazoles and, given the ubiquity of the CuAAC reaction, it should find application in organic synthesis, medicinal chemistry, chemical biology and materials science.
Synthesis and Explosion Hazards of 4-Azido- l -phenylalanine
Richardson, Mark B.,Brown, Derek B.,Vasquez, Carlos A.,Ziller, Joseph W.,Johnston, Kevin M.,Weiss, Gregory A.
, p. 4525 - 4536 (2018/04/26)
A reliable, scalable, cost-effective, and chromatography-free synthesis of 4-azido-l-phenylalanine beginning from l-phenylalanine is described. Investigations into the safety of the synthesis reveal that the Ullman-like Cu(I)-catalyzed azidation step does not represent a significant risk. The isolated 4-azido-l-phenylalanine product, however, exhibits previously undocumented explosive characteristics.
Puromycin Analogues Capable of Multiplexed Imaging and Profiling of Protein Synthesis and Dynamics in Live Cells and Neurons
Ge, Jingyan,Zhang, Cheng-Wu,Ng, Xue Wen,Peng, Bo,Pan, Sijun,Du, Shubo,Wang, Danyang,Li, Lin,Lim, Kah-Leong,Wohland, Thorsten,Yao, Shao Q.
supporting information, p. 4933 - 4937 (2016/04/26)
Newly synthesized proteins constitute an important subset of the proteome involved in every cellular process, yet existing chemical tools used to study them have major shortcomings. Herein we report a suite of cell-permeable puromycin analogues capable of being metabolically incorporated into newly synthesized proteins in different mammalian cells, including neuronal cells. Subsequent labeling with suitable bioorthogonal reporters, in both fixed and live cells, enabled direct imaging and enrichment of these proteins. By taking advantage of the mutually orthogonal reactivity of these analogues, we showed multiplexed labeling of different protein populations, as well as quantitative measurements of protein dynamics by fluorescence correlation spectroscopy, could be achieved in live-cell environments. Tag and see: A suite of cell-permeable puromycin analogues that are capable of multiplexed imaging of newly synthesized proteins in live cells and neurons has been developed. For the first time, diffusion dynamics of newly synthesized proteins inside live neuron-like dendritic cells were quantitatively measured, revealing a heterogeneous behavior.
A diversity-oriented synthesis strategy enabling the combinatorial-type variation of macrocyclic peptidomimetic scaffolds
Isidro-Llobet, Albert,Hadje Georgiou, Kathy,Galloway, Warren R. J. D.,Giacomini, Elisa,Hansen, Mette R.,Méndez-Abt, Gabriela,Tan, Yaw Sing,Carro, Laura,Sore, Hannah F.,Spring, David R.
supporting information, p. 4570 - 4580 (2015/04/14)
Macrocyclic peptidomimetics are associated with a broad range of biological activities. However, despite such potentially valuable properties, the macrocyclic peptidomimetic structural class is generally considered as being poorly explored within drug discovery. This has been attributed to the lack of general methods for producing collections of macrocyclic peptidomimetics with high levels of structural, and thus shape, diversity. In particular, there is a lack of scaffold diversity in current macrocyclic peptidomimetic libraries; indeed, the efficient construction of diverse molecular scaffolds presents a formidable general challenge to the synthetic chemist. Herein we describe a new, advanced strategy for the diversity-oriented synthesis (DOS) of macrocyclic peptidomimetics that enables the combinatorial variation of molecular scaffolds (core macrocyclic ring architectures). The generality and robustness of this DOS strategy is demonstrated by the step-efficient synthesis of a structurally diverse library of over 200 macrocyclic peptidomimetic compounds, each based around a distinct molecular scaffold and isolated in milligram quantities, from readily available building-blocks. To the best of our knowledge this represents an unprecedented level of scaffold diversity in a synthetically derived library of macrocyclic peptidomimetics. Cheminformatic analysis indicated that the library compounds access regions of chemical space that are distinct from those addressed by top-selling brand-name drugs and macrocyclic natural products, illustrating the value of our DOS approach to sample regions of chemical space underexploited in current drug discovery efforts. An analysis of three-dimensional molecular shapes illustrated that the DOS library has a relatively high level of shape diversity.
A simple quick route to fullerene amino acid derivatives
Strom, T. Amanda,Barron, Andrew R.
supporting information; experimental part, p. 4764 - 4766 (2010/09/16)
Two new fullerene amino acids have been prepared by dipolar addition to C60 of either the Boc- or Fmoc-Nα-protected azido amino acids derived from phenylalanine and lysine. UV-visible and CV studies indicate the as prepared amino acids are a mi
Nitrene addition to exfoliated graphene: A one-step route to highly functionalized graphene
Strom, T. Amanda,Dillon, Eoghan P.,Hamilton, Christopher E.,Barron, Andrew R.
supporting information; experimental part, p. 4097 - 4099 (2010/08/22)
We demonstrate a high yield method of functionalizing graphene nanosheets through nitrene addition of azido-phenylalanine [Phe(N3)] to exfoliated micro-crystalline graphite (μG). This method provides a direct route to highly functionalized grap
Synthesis of aryl azides and vinyl azides via proline-promoted CuI-catalyzed coupling reactions.
Zhu, Wei,Ma, Dawei
, p. 888 - 889 (2007/10/03)
The coupling reaction of aryl halides or vinyl iodide with sodium azide under catalysis of CuI/L-proline works at relatively low temperature to provide aryl azides or vinyl azides in good to excellent yields.
Structure-binding relation of philanthotoxins from nicotinic acetylcholine receptor binding assay
Nakanishi, Koji,Huang, Xuefei,Jiang, Hong,Ying, Liu,Fang, Kan,Huang, Danwen,Choi, Seok-Ki,Katz, Elizabeth,Eldefrawi, Mohyee
, p. 1969 - 1988 (2007/10/03)
Philanthotoxins are noncompetitive inhibitors of the nicotinic acetylcholine receptor and the various glutamate receptors. Analogues carrying photoaffinity labels, fluorine atoms for solid-state NMR studies of ligand/receptor interaction, and large head g
