391624-46-7Relevant academic research and scientific papers
Solid-phase synthesis of oligourea peptidomimetics employing the Fmoc protection strategy
Boeijen,Van Ameijde,Liskamp
, p. 8454 - 8462 (2001)
A solid-phase-Fmoc-based-synthesis strategy is described for oligourea peptidomimetics as well as a convenient general synthesis approach for the preparation of the required building blocks 5a-j and 5k. These are suitable for use in peptide or robot synthesizers, which is illustrated by the synthesis of oligourea peptidomimetics of part of Leu-enkephalin (10) and a neurotensin derivative (17).
LIGAND LINKER SUBSTRATE
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Page/Page column 13-15, (2020/07/15)
Ligand functionalized substrate including a solid substrate, which has been modified to provide grafted catching ligand groups covalently bound via a linker, methods of preparing said ligand functionalized substrate and the use thereof, such as to increase binding rate and the dynamic binding capacity (DBC).
Tri-Orthogonal Scaffolds for the Solid-Phase Synthesis of Peptides
Pícha, Jan,Fabre, Benjamin,Budě?ínsky, Milo?,Hajduch, Jan,Abdellaoui, Mehdi,Jirá?ek, Ji?í
supporting information, p. 5180 - 5192 (2018/08/01)
Multi-orthogonal scaffolds can be useful for the attachment of several different compounds to the same central skeleton. Such compounds can find applications in the development of protein mimics because of their potential to mimic several distant epitopes
PEPTIDE NUCLEIC ACID (PNA) MONOMERS WITH AN ORTHOGONALLY PROTECTED ESTER MOIETY
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, (2018/10/19)
This application pertains to orthogonally protected esters of peptide nucleic acid (PNA) monomers, which ester groups can be removed under conditions that permit typical backbone and side chain acid- and base-labile protecting groups to remain substantially intact thereby permitting the high yield of PNA monomer carboxylic acids that are suitable for use in PNA oligomer synthesis. Exemplary ester groups include, but are not limited to, 2,2,2-trichloroethyl (TCE), 2,2,2-tribromoethyl (TBE), 2-bromoethyl (2-BE) and 2-iodoethyl groups (2-IE). This invention also pertains to novel methods for the synthesis of Backbone Ester compounds and related Backbone Ester Acid Salts.
Flow-mediated synthesis of Boc, Fmoc, and Dd iv monoprotected diamines
Jong, Thingsoon,Bradley, Mark
supporting information, p. 422 - 425 (2015/03/03)
A series of monoprotected aliphatic diamines (21 examples) were synthesized via continuous flow methods. The carbamates and enamines were obtained in 45-91% yields using a 0.5 mm diameter PTFE tubular flow reactor. Using readily accessible protecting group precursors, the procedure serves as an attractive alternative to existing batch-mode synthetic routes by providing direct, multigram access to N-Boc-, N-Fmoc-, and N-Ddiv-protected compounds with productivity indexes of 1.2-3.6 g/h.
A ratiometric fluorescent nanoprobe for H2O2 sensing and in vivo detection of drug-induced oxidative damage to the digestive system
Wu, Guangfei,Zeng, Fang,Yu, Changmin,Wu, Shuizhu,Li, Wensheng
, p. 8528 - 8537 (2015/02/19)
Hydrogen peroxide is a biologically important reactive oxygen species (ROS) and plays crucial roles in living organisms. Herein, a FRET-based ratiometric fluorescent probe has been developed for detecting H2O2in vitro and in vivo. In this nanoprobe, carbon dots serve as the energy donor and carrier for the H2O2 recognition element. This nanoprobe exhibits fast-response, low toxicity, high sensitivity (with a detection limit of 0.5 μM) and selectivity towards H2O2 over other reactive oxygen or nitrogen species. The nanoprobe has been successfully applied in the detection of H2O2 in live cells and in zebrafish larvae. By incubating the nanoprobe with zebrafishes, the nanoprobe can be absorbed by the fishes within 1 h and accumulates mainly in the abdominal region. Due to its small size (～4 nm), the nanoprobe is gradually excreted by zebrafishes without long-term accumulation. Moreover, as the first ratiometric chemoprobe that can detect H2O2in vivo, the nanoprobe has been found capable of detecting and locating endogenous H2O2 in zebrafishes as a result of drug-induced oxidative damage. The successful detection of H2O2 by the nanoprobe in vivo may support its eventual use in clinical applications.
Molecular recognition of surface-immobilized carbohydrates by a synthetic lectin
Rauschenberg, Melanie,Fritz, Eva-Corrina,Schulz, Christian,Kaufmann, Tobias,Ravoo, Bart Jan
supporting information, p. 1354 - 1364 (2014/07/22)
The molecular recognition of carbohydrates and proteins mediates a wide range of physiological processes and the development of synthetic carbohydrate receptors ("synthetic lectins") constitutes a key advance in biomedical technology. In this article we report a synthetic lectin that selectively binds to carbohydrates immobilized in a molecular monolayer. Inspired by our previous work, we prepared a fluorescently labeled synthetic lectin consisting of a cyclic dimer of the tripeptide Cys-His-Cys, which forms spontaneously by air oxidation of the monomer. Amine-tethered derivatives of N-acetylneuraminic acid (NANA), β-D-galactose, β-Dglucose and α-D-mannose were microcontact printed on epoxide-terminated self-assembled monolayers. Successive prints resulted in simple microarrays of two carbohydrates. The selectivity of the synthetic lectin was investigated by incubation on the immobilized carbohydrates. Selective binding of the synthetic lectin to immobilized NANA and β-D-galactose was observed by fluorescence microscopy. The selectivity and affinity of the synthetic lectin was screened in competition experiments. In addition, the carbohydrate binding of the synthetic lectin was compared with the carbohydrate binding of the lectins concanavalin A and peanut agglutinin. It was found that the printed carbohydrates retain their characteristic selectivity towards the synthetic and natural lectins and that the recognition of synthetic and natural lectins is strictly orthogonal.
N-urethane-protected amino alkyl isothiocyanates: Synthesis, isolation, characterization, and application to the synthesis of thioureidopeptides
Sureshbabu, Vommina V.,Naik, Shankar A.,Hemantha,Narendra,Das, Ushati,Guru Row, Tayur N.
supporting information; experimental part, p. 5260 - 5266 (2009/12/06)
(Chemical Equation Presented) Synthetically useful N-Fmoc amino-alkyl isothiocyanates have been described, starting from protected amino acids. These compounds have been synthesized in excellent yields by thiocarbonylation of the monoprotected 1,2-diamines with CS2/TEA/p-TsCl, isolated as stable solids, and completely characterized. The procedure has been extended to the synthesis of amino alkyl isothiocyanates from Boc- and Z-protected amino acids as well. The utility of these isothiocyanates for peptidomimetics synthesis has been demonstrated by employing them in the preparation of a series of dithioureidopeptide esters. Boc-Gly-OH and Boc-Phe-OH derived isothiocyanates 9a and 9c have been obtained as single crystals and their structures solved through X-ray diffraction. They belong to the orthorhombic crystal system, and have a single molecule in the asymmetric unit (Z′ = 1). 9a crystallizes in the centrosymmetric space group Pbca, while 9c crystallizes in the noncentrosymmetric space group P212121.
