104091-09-0Relevant articles and documents
Fmoc-OPhth, the reagent of Fmoc protection
Yoshino, Ryo,Tokairin, Yoshinori,Kikuchi, Mari,Konno, Hiroyuki
, p. 1600 - 1603 (2017)
Fmoc-OSu has been widely used for Fmoc protection of amino groups, especially amino acids, in solid phase peptide synthesis. However, it has been recognized that Fmoc-βAla-OH is formed as a by-product via the Lossen rearrangement during the reaction. Since we reconfirmed the formation of Fmoc-βAla-OH during the preparation of Fmoc-AA-OH by Fmoc-OSu, Fmoc-OPhth was designed and synthesized as a new Fmoc reagent to avoid the formation of Fmoc-βAla-OH. Furthermore, Fmoc protection by Fmoc-OPhth and Fmoc-SPPS were evaluated. The various Fmoc-amino acids prepared by Fmoc-OPhth were carried out in good yields and these are applicable in Fmoc-SPPS.
Benzotriazole reagents for the syntheses of Fmoc-, Boc-, and Alloc-protected amino acids
Ibrahim, Tarek S.,Tala, Srinivasa R.,El-Feky, Said A.,Abdel-Samii, Zakaria K.,Katritzky, Alan R.
, p. 2013 - 2016 (2011)
Stable Fmoc-, Boc-, and Alloc-benzotriazoles react with various amino acids including unprotected serine and glutamic acid, in the presence of triethylamine at 20° as reagents to introduce -amino protecting groups to afford Fmoc-, Boc-, and Alloc-protected amino acids (77-94%) free of dipeptide and tripeptide impurities. Fmoc-, and Alloc-Gly-Gly-OH dipeptides were prepared in 90% yields by N-acylation of glycylglycine with Fmoc- and Alloc-benzotriazoles in the presence of triethylamine. Synthesized N-protected amino acids were greater than 99% pure, analyzed by HPLC. Georg Thieme Verlag Stuttgart - New York.
Liquid-chromatography quantitative analysis of 20 amino acids after derivatization with FMOC-CI and its application to different origin Radix isatidis
Zhou, Wei,Zhang, Xiao-Yan,Duan, Geng-Li
, p. 509 - 515 (2011)
We developed a simple, rapid and reliable method for determination of 20 common amino acids based on derivatization with 9-fluorenylmethyl chloroformate (FMOC-CI) and RP-LC/UV, this method was first introduced into quantitative analysis of amino acids. The amino groups of amino acids were trapped with FMOC-CI to form amino acid-FMOC-Cl adducts which can be suitable for LC-UV. Chromatographic separation was performed on a C18 column with a mobile phase gradient consisting of acetonitrile and sodium acetate solution. This method was shown to be sensitive for 20 common amino acids. In the intra-day precisions assay, the range of RSDs was 3.21-7.67% with accuracies of 92.34-102.51%; for the inter-day precisions assay, the range of RSDs was 5.82-9.19% with accuracies of 90.25-100.63%. The results also indicated that solutions of amino acids-FMOC-Cl can be kept at room temperature for at least 24 h without showing significant losses in the quantified values. The validated method was successfully applied to the determination of major four kinds of amino acids in R. isatidis samples (Arg, Pro, Met and Val). The total content of amino acids in different origin R. isatidis was 13.32-19.16 mg/g. The differences between R. isatidis samples were large using HCA.
Molecular Scaffolds as Double-Targeting Agents For the Diagnosis and Treatment of Neuroblastoma
Villaverde, Gonzalo,Alfranca, Arantzazu,Gonzalez-Murillo, áfrica,Melen, Gustavo J.,Castillo, Rafael R.,Ramírez, Manuel,Baeza, Alejandro,Vallet-Regí, María
, p. 3067 - 3072 (2019)
The selective delivery of therapeutic and imaging agents to tumoral cells has been postulated as one of the most important challenges in the nanomedicine field. Meta-iodobenzilguanidine (MIBG) is widely used for the diagnosis of neuroblastoma (NB) due to its strong affinity for the norepinephrine transporter (NET), usually overexpressed on the membrane of malignant cells. Herein, a family of novel Y-shaped scaffolds has been synthesized, which have structural analogues of MIBG covalently attached at each end of the Y-structure. The cellular uptake capacity of these double-targeting ligands has been evaluated in vitro and in vivo, yielding one specific Y-shaped structure that is able to be engulfed by the malignant cells, and accumulates in the tumoral tissue, at significantly higher levels than the structure containing only one single targeting agent. This Y-shaped ligand can provide a powerful tool for the current treatment and diagnosis of this disease.
Conjugate (MTC-220) of muramyl dipeptide analogue and paclitaxel prevents both tumor growth and metastasis in mice
Ma, Yao,Zhao, Nan,Liu, Gang
, p. 2767 - 2777 (2011)
1 (MTC-220), a conjugate of paclitaxel and a muramyl dipeptide analogue, has been synthesized as a novel agent of dual antitumor growth and metastasis activities. In vitro and in vivo tests show that 1 retains its ability to inhibit tumor growth. It is su
New TFA-free cleavage and final deprotection in Fmoc solid-phase peptide synthesis: Dilute HCl in fluoro alcohol
Palladino, Pasquale,Stetsenko, Dmitry A.
, p. 6346 - 6349 (2012)
A novel method for cleaving from resin and removing acid-labile protecting groups for the Fmoc solid-phase peptide synthesis is described. 0.1 N HCl in hexafluoroisopropanol or trifluoroethanol cleanly and rapidly removes the tert-butyl ester and ether, Boc, trityl, and Pbf groups and cleaves the common resin linkers: Wang, HMPA, Rink amide, and PAL. Addition of just 5-10% of a hydrogen-bonding solvent considerably retards or even fully inhibits the reaction. However, a non-hydrogen-bonding solvent is tolerated.
Multicomponent hydrogels from enantiomeric amino acid derivatives: Helical nanofibers, handedness and self-sorting
Adhikari, Bimalendu,Nanda, Jayanta,Banerjee, Arindam
, p. 8913 - 8922 (2011)
In this study, chiral helical nanofibers have been obtained from suitable, co-assembling, two oppositely charged amino acid based two component hydrogels. An equimolar mixture of an N-terminally protected amino acid Fmoc-(l/d)Glu (Fmoc: N-fluorenyl-9-methoxycarbonyl, Glu: glutamic acid) and (l/d)Lys (Lys: lysine) can co-assemble to form hydrogels. These hydrogels have been characterised using circular dichroism (CD), atomic force microscopy (AFM), transmission electron microscopy (TEM), X-ray powder diffraction, fluorescence spectroscopic and rheological studies. CD and AFM studies have been extensively used to examine the chiral/achiral nature of fibers obtained from different hydrogel systems. The equimolar mixture of two l-isomers, {Fmoc-(l)Glu + (l)Lys} in the assembled state, leads to the exclusive formation of left-handed helical nanofibers, whereas an equimolar mixture of two d-isomers, {Fmoc-(d)Glu + (d)Lys}, gives rise to right-handed helical nanofibers. The CD study of the gel obtained from the {Fmoc-(l)Glu + (l)Lys} system is exactly the mirror image of the CD signal obtained from the gel of the {Fmoc-(d)Glu + (d)Lys} system. These results suggest that the molecular chirality is being translated into the supramolecular helicity and the handedness of these fibers depends on the corresponding molecular chirality in the mixture of the two component system. Reversing the handedness of helical fibers is possible by using enantiomeric building blocks. Co-assembly of racemic and equimolar mixtures of all four components, i.e., [{Fmoc-(l)Glu + (l)Lys} + {Fmoc-(d)Glu + (d)Lys}] can also form hydrogels. Interestingly, in this racemic mixture self-sorting has been observed with the presence of almost equal amount of left- and right-handed helical nanofibers. The equimolar mixture of Fmoc-(l)Glu and l-ornithine/l-arginine also produces hydrogel with left-handed helical fibers. Moreover, the straight fiber has been observed from the two component hydrogel {Fmoc-(l)Glu + (l)Lys} system in the presence of Ca2+/Mg2+ ions. This indicates the straight nanofibers are obtained under suitable conditions and acid-base interaction is responsible for making the helical fibers at the nanoscale.
Easy saponification by metal silanolates: Application in SPPS and in (S)-5-hydroxynorvaline preparation
Minta, Ewelina,Boutonnet, Cédric,Boutard, Nicolas,Martinez, Jean,Rolland, Valérie
, p. 1795 - 1797 (2005)
Alkali metal trimethylsilanolates, TMSO-, M+, has been used for efficient conversion of methyl esters into their corresponding anhydrous acid salts under mild non-aqueous conditions. This strategy has been applied to SPPS for the preparation of neurotoxin cyclic analogues and in (S)-5-hydroxynorvaline synthesis.
SUPRAMOLECULAR GEL SUPPORTED ON OPEN-CELL POLYMER FOAM
-
Page/Page column 16-17, (2021/03/19)
The present invention relates to a polymer foam, said polymer foam comprising pores forming an open-cell polymer foam, said polymer foam comprising a supramolecular gel inside pores, and said polymer foam comprising at least one enzyme. The present invention relates to a supramolecular gel; its preparation and its applications, notably in chemical synthesis and kinetic resolution, in particular of organic compounds. The present invention also relates to flow chemistry.
Preparation method of N-fluorenylmethoxycarbonyl-gamma-(S-triphenylmethyl-cysteamine)-L-glutamic acid
-
Paragraph 0026, (2020/10/05)
The invention provides a preparation method of N-fluorenylmethoxycarbonyl-gamma-(S-triphenylmethyl-cysteamine)-L-glutamic acid. The preparation method mainly solves the technical problems of complexity, long period, high cost, and low yield of an original process, and comprises the following steps: (1) preparing N-fluorenylmethoxycarbonyl-L-glutamic acid; (2) preparing N-fluorenylmethoxycarbonyl-L-glutamic acid-1-benzyl ester; (3) preparing S-triphenylmethyl cysteamine; (4) preparing N-fluorenylmethoxycarbonyl-gamma-(S-triphenylmethyl-cysteamine)-L-glutamic acid-alpha-benzyl ester; and (5) preparing N-fluorenylmethoxycarbonyl-gamma-(S-triphenylmethyl-cysteamine)-L-glutamic acid. The method is rapid, high in yield and simple in separation and purification, and the used solvent is environment-friendly and is suitable for mass production.
