175844-11-8Relevant articles and documents
Synthesis and characterization of selenium(I/II) and tellurium(IV) derivatives of amino acids
Singh, Puspendra,Singh, Harkesh B.,Butcher, Ray J.
, p. 1 - 9 (2018)
The direct reaction between Te metal and methyl 2-(2-bromoacetamido)propanoate (27) at room temperature, yields the first example of organotellurium(IV) derivative (MeOC(O)CH(Me)NHCOCH2)2TeBr2 (31). Similarly, reaction of Te with methyl 2-(2-bromoacetamido)acetate (26) and methyl 2-(2-bromoacetamido)-3-phenylpropanoate (28) in presence of NaI in acetone gives MeOC(O)CH2NHCOCH2I (29), MeOC(O)CH(R)NHCOCH2)2TeI2 (R = H (30) and CH2Ph (32). Treatment of 26/27/28 with Li2Te2/Li2Se2 readily provides the [MeOC(O)CH(CH3)NHCOCH2]2Te2, (33); [MeOC(O)CH2NHCOCH2]2Se2, (34); [MeOC(O)CH(CH2Ph)NHCOCH2]2Se2, (35) and [Figure presented] (36). Similarly the reaction of (2,6-dimethyl-4-tert-butylC6H2)SeNa with 28 readily provide the [MeOC(O)CH(CH2Ph)NHCOCH2]SeC6H2-2,6-dimethyl-4-tert-butyl), (37) in good yield. Molecule [MeOC(O)CHNH(Boc)CH2]2Se2, (38) and [NaOC(O)CHNH(Boc)CH2Te(2,4,6-Me3C6H2] (39) were prepared by the treatment of Li2Se2/2,4,6-Me3C6H2TeNa with methyl 3-bromo-2-((tert-butoxycarbonyl)amino)propanoate and N-(t-Boc)-L-serine β-lactone respectively. These compounds are purified by chromatography and characterized by a number of analytical techniques such as (1H, 13C, 77Se and 125Te NMR) spectroscopy, mass spectrometry and elemental analysis. The single crystal X-ray studies of 29, 30, 31, 36 and 38 revealed the presence of characteristic O?Se/Te, secondary bonding interactions. A detailed analysis of the crystal structures of the compound reveals interesting supramolecular assembly.
Modelling the site of bromide binding in vanadate-dependent bromoperoxidases
Kraehmer, Verena,Rehder, Dieter
, p. 5225 - 5234 (2012)
Treatment of Boc-protected (S)-serine (Ser) methyl ester with triphenylphosphine bromide Ph3PBr (intermittently generated from PPh3 and N-bromosuccinimide) yields Boc-3-bromoalanine (R)-Boc-BrAlaMe and, after deprotection, bromoalani
Synthesis of novel unnatural amino acid as a building block and its incorporation into an antimicrobial peptide
Oh, Jong Eun,Lee, Keun Hyeung
, p. 2985 - 2990 (1999)
Considering the biological mechanism and in vivo stability of antimicrobial peptides, we designed and synthesized novel unnatural amino acids with more positively charged and bulky side chain group than lysine residue. The unusual amino acids, which were synthesized by either solution phase or solid phase, were incorporated into an antimicrobial peptide. Its effect on the stability, activity, and the structure of the peptide was studied to evaluate the potential of these novel unnatural amino acids as a building block for antimicrobial peptides. The incorporation of this unusual amino acid increased the resistance of the peptide against serum protease more than three times without a decrease in the activity. Circular dichroism spectra of the peptides indicated that all novel unnatural amino acids must have lower α helical forming propensities than lysine. Our results indicated that the unnatural amino acids synthesized in this study could be used not only as a novel building block for combinatorial libraries of antimicrobial peptides, but also for structure-activity relationship studies about antimicrobial peptides. Copyright (C) 1999 Elsevier Science Ltd.
Method to build 2,4-substituted selenazole from β-azido diselenide and carboxylic acid: A formal synthesis of selenazofurin
Qiao, Junfei,Liu, Yi,Du, Yuguo
, p. 3061 - 3068 (2018)
A novel approach for the synthesis of 2,4-disubstituted selenazoles using carboxylic acids (or anhydrides) and β-azido diselenide was achieved via a one-pot cascade formation of selenazoline (Staudinger reduction/diselenide cleavage/selenocarbonylation/az
Synthesis of Enantiopure Unnatural Amino Acids by Metallaphotoredox Catalysis
Faraggi, Tomer M.,Rouget-Virbel, Caroline,Rincón, Juan A.,Barberis, Mario,Mateos, Carlos,García-Cerrada, Susana,Agejas, Javier,De Frutos, Oscar,Macmillan, David W. C.
supporting information, p. 1966 - 1973 (2021/08/18)
We describe herein a two-step process for the conversion of serine to a wide array of optically pure unnatural amino acids. This method utilizes a photocatalytic cross-electrophile coupling between a bromoalkyl intermediate and a diverse set of aryl halides to produce artificial analogues of phenylalanine, tryptophan, and histidine. The reaction is tolerant of a broad range of functionalities and can be leveraged toward the scalable synthesis of valuable pharmaceutical scaffolds via flow technology.
Design and synthesis of selenazole-substituted ritonavir analogs
Qiao, Junfei,Zhao, Chuanfang,Liu, Jun,Du, Yuguo
supporting information, p. 2379 - 2381 (2018/06/25)
With the help of Surflex-Dock calculation, two ritonavir analogs in which one thioazole unit was replaced by selenazole have been designed and synthesized. The key selenazole structure was constructed from β-azido diselenide through a cascade diselenide cleavage/selenocarbonylation/Staudinger reduction/aza-Wittig reaction and a following MnO2 oxidation. The accordingly prepared compounds exhibited good anti-HIV-1 (IIIB) activities comparable to that of the original ritonavir, as well as the positive SI values.
OPTICALLY ACTIVE -AMINO ACID INTO WHICH BSH IS INTRODUCED AND METHOD FOR SYNTHESIZING THE SAME
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, (2011/05/14)
Disclosed is the method for producing an optically active BSH amino acid, which comprises a step of reacting an optically active α-amino acid derivative having a halogen in a side chain with a cyanoethyl BSH compound represented by formula (1). An optically active BSH amino acid obtained by the method is also disclosed.
Evaluation of α-pyrones and pyrimidones as photoaffinity probes for affinity-based protein profiling
Battenberg, Oliver A.,Nodwell, Matthew B.,Sieber, Stephan A.
experimental part, p. 6075 - 6087 (2011/10/09)
α-Pyrones and pyrimidones are common structural motifs in natural products and bioactive compounds. They also display photochemistry that generates high-energy intermediates that may be capable of protein reactivity. A library of pyrones and pyrimidones was synthesized, and their potential to act as photoaffinity probes for nondirected affinity-based protein profiling in several crude cell lysates was evaluated. Further "proof-of-principle" experiments demonstrate that a pyrimidone tag on an appropriate scaffold is equally capable of proteome labeling as a benzophenone.
Internally stabilized selenocysteine derivatives: Syntheses, 77Se NMR and biomimetic studies
Phadnis, Prasad P.,Mugesh
, p. 2476 - 2481 (2007/10/03)
Selenocystine ([Sec]2) and aryl-substituted selenocysteine (Sec) derivatives are synthesized, starting from commercially available amino acid L-serine. These compounds are characterized by a number of analytical techniques such as NMR (1H, 13C and 77Se) and TOF mass spectroscopy. This study reveals that the introduction of amino/imino substituents capable of interacting with selenium may stabilize the Sec derivatives. This study further suggests that the oxidation-elimination reactions in Sec derivatives could be used for the generation of biologically active selenols having internally stabilizing substituents. The Royal Society of Chemistry 2005.
Synthesis of a selenocysteine-containing peptide by native chemical ligation
Gieselman, Matt D.,Xie, Lili,Van Der Donk, Wilfred A.
, p. 1331 - 1334 (2007/10/03)
(equation presented) A new method for the synthesis of selenocysteine derivatives and selenocysteine-containing peptides is described. Fmoc-Se-p-methoxybenzylselenocysteine (1) was prepared and used for solid-phase synthesis of peptides with an N-terminal unprotected selenocysteine. Subsequent native chemical ligation with a peptide thioester provided a 17-mer that corresponds to the C-terminus of ribonucleotide reductase with selenocysteine in place of cysteine.
