109425-55-0Relevant articles and documents
Improved scalable syntheses of mono- and bis-urethane derivatives of ornithine
Wiejak,Masiukiewicz,Rzeszotarska
, p. 1189 - 1191 (2001)
In the search for a practical route to ornithine bisurethane derivatives useful for peptide synthesis, we elaborated the simple and efficient (86% yield) synthesis of Nε-tert-butoxycarbonyl-L-ornithine copper(II) complex(1). This served as substrate for obtaining Nε-tert-butoxycarbonyl-L-ornithine (2), Nα-benzyloxycarbonyl-Nε-tert- butoxycarbonyl-L-ornithine (3) and Nα-(9-fluorenyl)methoxycarbonyl-Nε-tert- butoxycarbonyl-L-ornithine (4). These were synthesized in 94-95% yields and with a purity above 99%.
Tri-peptide cationic lipids for gene delivery
Zhao, Yinan,Zhang, Shubiao,Zhang, Yuan,Cui, Shaohui,Chen, Huiying,Zhi, Defu,Zhen, Yuhong,Zhang, Shufen,Huang, Leaf
, p. 119 - 126 (2015)
Several novel tri-peptide cationic lipids were designed and synthesized for delivering DNA and siRNA. They have tri-lysine and tri-ornithine as headgroups, a carbamate group as a linker and 12 and 14 carbon atom alkyl groups as tails. These tri-peptide cationic lipids were prepared into cationic liposomes for the study of the physicochemical properties and gene delivery. Their particle size, zeta potential and DNA-binding were characterized to show that they were suitable for gene transfection. Further results indicate that these lipids can transfer DNA and siRNA very efficiently into NCI-H460 and Hep-2 tumor cells. The selected lipid, CDO14, was able to deliver combined siRNAs against c-Myc and VEGF for silencing distinct oncogenic pathways in lung tumors of mice, with little in vitro and in vivo toxicity. This journal is
An efficient and economical method for the preparation of Fmoc-Arg ωω (Boc) 2-OH
Zhu, Ruixin,Xie, Ming,Wang, Fei,Liu, Qi,Kang, Tingguo
, p. 1508 - 1509 (2010)
The arginine derivative Fmoc-Arg omega;ω″(Boc) 2-OH has been prepared in perfect yield starting from Fmoc-Orn?HCl and N,N′-di-Boc-N″-triflyguanidine with the presence of diisopropylethylamine (DIEA). This work provides an efficient a
COMPOUND FOR PREPARATION OF ANTIBODY-PAYLOAD CONJUGATE AND USE THEREOF
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, (2022/03/15)
The present application relates to a novel linker for use in bioconjugation, comprising two or more electrophilic carbon atoms of a carbonyl group, and a click chemistry functional group and, more specifically, to a linker through which a compound, a peptide, and/or a protein can be directly and/or indirectly linked by a substitution reaction to a desired target molecule, that is, a target molecule.
Optimized syntheses of Fmoc azido amino acids for the preparation of azidopeptides
Pícha, Jan,Budě?ínsky, Milo?,Machá?ková, Kate?ina,Collinsová, Michaela,Jirá?ek, Ji?í
, p. 202 - 214 (2017/04/06)
The rise of CuI-catalyzed click chemistry has initiated an increased demand for azido and alkyne derivatives of amino acid as precursors for the synthesis of clicked peptides. However, the use of azido and alkyne amino acids in peptide chemistry is complicated by their high cost. For this reason, we investigated the possibility of the in-house preparation of a set of five Fmoc azido amino acids: β-azido l-alanine and d-alanine, γ-azido l-homoalanine, δ-azido l-ornithine and ω-azido l-lysine. We investigated several reaction pathways described in the literature, suggested several improvements and proposed several alternative routes for the synthesis of these compounds in high purity. Here, we demonstrate that multigram quantities of these Fmoc azido amino acids can be prepared within a week or two and at user-friendly costs. We also incorporated these azido amino acids into several model tripeptides, and we observed the formation of a new elimination product of the azido moiety upon conditions of prolonged couplings with 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate/DIPEA. We hope that our detailed synthetic protocols will inspire some peptide chemists to prepare these Fmoc azido acids in their laboratories and will assist them in avoiding the too extensive costs of azidopeptide syntheses. Experimental procedures and/or analytical data for compounds 3–5, 20, 25, 26, 30 and 43–47 are provided in the supporting information.
PROPYL CATIONIC PEPTIDE LIPIDS, SYNTHESIS METHOD THEREOF, AND APPLICATION THEREOF
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Paragraph 0059; 0069; 0073; 0085, (2018/01/13)
A class of propyl cationic peptide lipids is propyl cationic peptide lipid compounds having a general formula structure as follows. After the propyl cationic peptide lipids are dispersed in water, a cationic liposome with a particle size of approximately 100 nm is obtained. The cationic liposome can carry plasmid DNA (pDNA) or small interfering RNA (siRNA) into cells to realize the function of gene delivery, and is almost non-toxic to the cells.
The two pathways for effective orthogonal protection of L-ornithine, for amino acylation of 5'-O-Pivaloyl nucleosides, describe the general and important role for the successful imitation, during the synthesis of the model substrates for the ribosomal mimic reaction
Bayryamov, Stanislav G.,Vassilev, Nikolay G.,Petkov, Dimiter D.
, p. 889 - 898 (2011/12/14)
Bz(NO2)-Orn(Boc)-OCH2CN was synthesized as an amino acid component with effective and successful orthogonal protection for amino acylation of 5'-O-Pivaloyl nucleosides and preparation of substrates for model ribosome reactions. The synthesis was carried out using suitable combinations of the methods of peptide synthesis and modification of amino acids.
Efficient procedure for the preparation of oligomer-free N-fmoc amino acids
Nowshuddin, Shaik,Rao,Reddy, A. Ram
experimental part, p. 2022 - 2031 (2009/11/30)
A two-step method is presented for the peptide-free, high-purity, and high-yield synthesis of N-Fmoc amino acids. The first step involves the preparation of stable dicyclohexylammonium-amino acid ionic adduct in acetone. Subsequently, the ionic adducts, on reaction with Fmoc-Nosu under mild alkaline conditions, give dipeptide-free N-Fmoc amino acids. The positive charge of the dicyclohexylammonium counterion in the ionic salt has a longer radius, moderating the nucleophilicity of the carboxylate ion of the amino acid and preventing by-products by arresting the formation of mixed anhydrides, the precursors of oligopeptide impurities.
A convenient, general synthesis of 1,1-dimethylallyl esters as protecting groups for carboxylic acids
Sedighi, Minoo,Lipton, Mark A.
, p. 1473 - 1475 (2007/10/03)
(Chemical Equation Presented) Carboxylic acids were converted in high yield to their 1,1-dimethylallyl (DMA) esters in two steps. Palladium-catalyzed deprotection of DMA esters was shown to be compatible with tert-butyl, benzyl, and Fmoc protecting groups, and Fmoc deprotection could be carried out selectively in the presence of DMA esters. DMA esters were also shown to be resistant to nucleophilic attack, suggesting that they will serve as alternatives to tert-butyl esters when acidic deprotection conditions need to be avoided.
